Jon Stewart on a Knicks Disaster, the Soto Era, His ‘Daily Show’ Comeback, Bad Biden Coverage, and New York Fans | Plus: Is an OKC Title Now Inevitable?

Summary

Podcast Summary: The Bill Simmons Podcast Featuring Jon Stewart

Release Date: May 23, 2025

In this engaging episode of The Bill Simmons Podcast, host Bill Simmons sits down with renowned comedian and former Daily Show host Jon Stewart for an extensive conversation covering a wide array of topics. From the tumultuous performance of the New York Knicks in the NBA playoffs to Jon Stewart's illustrious career in comedy and media, the duo delves deep into sports, politics, media authenticity, and personal anecdotes. Below is a detailed summary capturing the essence of their discussion.

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1. Knicks' Playoff Struggles and OKC's Dominance

The episode kicks off with Bill Simmons analyzing the New York Knicks' disappointing Game 1 loss in the playoffs. He expresses significant concern about the team's ability to advance, citing their poor performance and defensive weaknesses. Simmons highlights the Oklahoma City Thunder's (OKC) remarkable season, noting their stellar point differential and robust defense.

Notable Quote:

Bill Simmons (00:03:00): "OKC might only lose three games in this entire playoffs the way this is going. So they're 78 and 17 for the season right now. And if you go historically, I did this last year because it seemed like the Celtics had a chance to go 80 and 20 in the season. The Bulls were 87 and 13 in 1996. That is, that's the mark. I don't know if anyone's beating that in our lifetimes."

Simmons draws parallels between OKC's potential dominance and historic NBA teams, arguing that OKC could cement their place in all-time great discussions if they continue their current trajectory.

2. Jon Stewart's Return and Reflections on Comedy

Jon Stewart joins the conversation, bringing his unique perspective from his time hosting The Daily Show. He reflects on his comedic journey, sharing insights into the challenges and rewards of building a career in comedy. Stewart recounts his early days in Greenwich Village, bartending while trying to break into stand-up comedy, and the camaraderie among comedians during that era.

Notable Quote:

Jon Stewart (01:15:15): "I just have nothing but ridiculously fond memories. And I'm sure there's a little gloss of nostalgia that carries over maybe some of the tougher times. But I think if it hadn't been somewhat painful and somewhat of a struggle, you know, it wouldn't mean much in the aftermath."

Stewart emphasizes the importance of authentic relationships and hard work in the entertainment industry, contrasting it with today's digital and performative landscape.

3. Evolution of Media and Authenticity

A significant portion of the discussion centers on the transformation of media, particularly the rise of social media and its impact on authenticity. Both Simmons and Stewart critique how public figures, including athletes and politicians, curate their personas online, often leading to a disconnect between their public image and reality.

Notable Quote:

Bill Simmons (05:27:05): "But they still think of authenticity as a strategy, which is the antithesis of authenticity."

Jon Stewart (05:28:02): "Now I feel like the whole thing is kayfabe. The whole thing is, you know, we talked about it on the show. It used to be the. It's not the crime, it's the COVID up. I feel like the whole thing is cover up."

They discuss the challenges of maintaining genuine authenticity in an era where image often trumps reality, leading to public backlash when discrepancies arise.

4. Impact of Social Media and Modern Media Consumption

The conversation shifts to how social media and streaming platforms have revolutionized content consumption. They explore the implications of having instant access to vast amounts of information and the pressure it places on media professionals to constantly perform and engage with audiences.

Notable Quote:

Jon Stewart (05:36:19): "People don't really know what's behind it. And then over and over again we find out, oh, that person was a maniac, or, oh, that person got caught, you know, behind the scenes saying this when they actually said this in public."

This segment critiques the superficiality fostered by social media, where depth and authenticity are often sacrificed for visibility and engagement.

5. Sports Media Influences and Comparisons

Bill Simmons draws parallels between sports broadcasting and political/media show dynamics, highlighting the influence of iconic sports shows like Mike and the Mad Dog's on the evolution of podcasting. They reminisce about the golden era of sports radio and its seamless blend with emerging media formats.

Notable Quote:

Bill Simmons (06:00:00): "I just feel like a lot of the people that have huge platforms now. And I include myself, were like, massively influenced by that specific show because of the interplay back and forth with those guys."

Jon Stewart (06:00:32): "But I always remain optimistic because there's too many. Look, I do too, on an individual basis. There's just too many fucking good people."

6. Personal Anecdotes and Relationships

Jon Stewart shares humorous and heartfelt stories about his family, particularly his interactions with his son and experiences with wrestling events. He recounts a memorable moment when he unexpectedly took a wrestling bump during a SummerSlam event, leading to playful teasing from Bill about his son's reaction.

Notable Quote:

Jon Stewart (07:00:25): "So I went out there and I'm up on Cena, who's gigantic and muscular, and he. And there was. There's no. Like, oh. Yeah, it looked like a. Do you know those, like, Instagram posts where they're like a friend group that takes the same picture every 10 years? And that was daunting because it was a very strange, like, kind of melancholy feeling of the evidence of, you know, decrepitude is too strong a word."

These personal stories add a relatable and entertaining layer to the conversation, showcasing the human side of both hosts.

7. Final Thoughts on Knicks and Broader Sports Insights

As the episode winds down, Simmons and Stewart revisit the Knicks' playoff prospects, discussing strategies and player performances that could influence the series outcome. They compare current Knicks dynamics to historic moments in sports, emphasizing the unpredictable nature of playoff basketball.

Notable Quote:

Bill Simmons (07:43:54): "What do you think 1993 Mike and the Mad Dog would have said about that loss last night?"

Jon Stewart (07:43:59): "It's a crapshoot. And the Dodgers are going to be there for a while and the Yankees are going to be there and. But they're at least you want sustainably good."

8. Closing Remarks and Future Outlook

In their closing moments, Simmons and Stewart reflect on the broader cultural and political climate, expressing concerns over media integrity and the future of political discourse. They emphasize the need for authentic leadership and the importance of media professionals maintaining their integrity amidst increasing polarization.

Notable Quote:

Jon Stewart (08:35:57): "What they do is, after these kinds of disruptions, you have to have kind of a more clear-eyed view of what it takes to bend that thing and where you want to bend it."

Bill Simmons (08:36:29): "I can't forgive the bump because that was crazy. Even if you were like 35, that would have been a crazy bump. That's a bump like past your 20s. I'm not taking. Making it."

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Key Takeaways:

• OKC Thunder's Playoff Potential: Bill Simmons provides a thorough analysis of OKC's dominant performance, suggesting they could achieve historic greatness if they maintain their current form.

• Jon Stewart's Comedic Journey: Stewart shares his path from a struggling comedian in Greenwich Village to hosting The Daily Show, highlighting the importance of authenticity and resilience.

• Media Authenticity: Both hosts critique the superficial nature of modern media, emphasizing the loss of genuine authenticity in public personas.

• Influence of Sports Radio on Modern Media: The episode draws connections between traditional sports broadcasting and contemporary podcasting, acknowledging the lasting impact of legendary shows.

• Personal Stories Enhance the Dialogue: Stewart's anecdotes about his family and unexpected experiences add depth and relatability to the discussion.

• Concerns Over Media and Political Integrity: The hosts express apprehensions about the current state of media and its role in shaping political narratives, advocating for honest and authentic journalism.

This episode offers listeners a rich blend of sports analysis, media critique, and personal storytelling, all anchored by the insightful dialogue between Bill Simmons and Jon Stewart. Whether you're a sports enthusiast, a media aficionado, or a fan of Jon Stewart's comedic prowess, this conversation provides valuable perspectives and entertaining moments.

Transcript

[Bill Simmons]

You're listening and watching the Bill Simmons podcast presented by FanDuel, our friends America's number one sportsbook, and they've made it easier than ever to get in on the action during an NBA playoff game, even after a tip off. Just look for the live SGP tab on the FanDuel Sportsbook app and build your own bet slip. Then sit back, relax, track the outcome of your parlay right in the app. And if you don't already have it, download the FanDuel app today to make every moment more the Ringer is committed to responsible gaming. Please visit rg-help.com to learn more about the resources and helplines available and listen to the end episode for additional details. Must be 21 + on President Select States gaming problem, call 100 GAMBLER visit rg-help.com Coming up, OKC Minnesota Game 2 + Jon Stewart on the Knicks in Life next. We're also brought to you by the Ringer Podcast Network where I put up a new rewatchables. On Monday night we did Close Encounters of the Third Kind. It is the third installment of Big Ass 70s Month. The last one will be on Monday night. We are doing Heaven Can Wait, a beloved movie for a lot of us with Warren Beatty and Julie Crystal. So you have five days to watch that. You can watch all the rewatchables episodes as video podcasts on Spotify, as on our Ringer Movies YouTube channel, or wherever you get your podcasts. So stay tuned for that. Coming up on this podcast, a long, long conversation with the one and only Jon Stewart. Because, and it's weird because I scheduled it before we knew that the Knicks were going to have a calamitous Game 1 loss. But we talked about the Knicks and New York Sports. We talked about his career, we talked about everything going on in the country. The Mets, you name it, we talked about it. It's a long, long combo. So I wanted to run that, as you know, the majority of the podcast, but wanted to put a little something at the top after watching OKC Minnesota Game 2. So we're going to talk about that right after Pearl Jam and then a lot of Jon Stewart. It's all next. Let's bring in our guys. Pearl Jam. All right, recording this part of the podcast a little after 8:30, right after game two. OKC Minnesota. OKC throttles Minnesota. And I gotta be honest, I'm a little concerned. I'm a little concerned for the rest of the playoffs because it feels like OKC, who was already a great team, who was already 68 and 14 during this season they had, they're plus 12.6 point differential. In the playoffs, they're plus 14. I mean we had lots of reasons to already be concerned that they were going to rip through the playoffs and be a juggernaut. The Denver series going seven maybe open the window to huh, maybe minute. No, their defense is just too good. This is, this is turning into some 2000 Ravens kind of stuff. Football analogy. 89 pistons, which was a totally different team because they, you know they, they were really built around the nine man concept. They didn't have the true superstar. As great as Isaiah was. This team is built around SGA who just scores between 30 and 40 points a game. No matter what the defense is doing. How many guys you. They're throwing traps, 45, 45ft from the basket doesn't matter. He's still getting the basket. I think at 38 or 40 tonight he was just fantastic. He's got this head to head battle against Anthony Edwards who everybody wants to be the future of the league because he's young, he's a little Jordany, he's American and SGA is just handing it to him in this series. Opponents in the playoffs are 40% field goal, 30% from three against them. Heading into this game they had 18.3 turnovers a game that they were forcing and the defense is just so much better than anything anyone else is doing. We have four teams left and I just don't know if anybody can touch this team. Vandal doesn't think so either because they're minus 310 to win the title. At this point Indiana might be our only chance because they don't turn the ball over. They're built around their guards. They play this kind of funky pace that makes you come to what they want to do and the pace they want to play at and maybe they can mess OKC up, but honestly I don't think it's going to matter. This, we got to this case this point a little bit with the Celtics last year where the math just becomes the math. If you have somebody that's winning 80% of their games, that's winning by between 10 and 15 points a game, that is deep and young and has defense and home court advantage, to flip it on them is going to be almost impossible. Which is why, you know, if there's a winner from these first two games, other than OKC and other than Indiana for their comeback of the century yesterday, Denver's gotta be feeling better about everything that happened. You know, they take this Crazy juggernaut of a team to seven and then get killed in game seven. But just even winning three games off this team, when you don't have a bench, when you have four guys, it's kind of nuts in retrospect. OKC might only lose three games in this entire playoffs the way this is going. So they're 78 and 17 for the season right now. And if you go historically, I did this last year because it seemed like the Celtics had a chance to go 80 and 20 in the season. The Bulls were 87 and 13 in 1996. That is, that's the mark. I don't know if anyone's beating that in our lifetimes. Lakers in 72 were 81 and 15. The 97 Bulls were 84 and 17. 17. Golden State is 84 and 16. And then the 67, 76ers were 79 and 17. And this OKC team right now is 78, 17, 84 and 17 is in play. Which means they would basically force themselves into the all time conversation. Even though we've been watching them going, I don't know, they're a little young. Jalen Williams, is he a good enough second banana? I don't know about these three point shooters. They're basically going to bulldoze their way into the all time conversation if this keeps going. And the thing that scares me, not just for the playoffs, but for the history stuff, is that it feels like they're getting better. It feels like defensively the whole flying around like pit Bulls thing, now they're turning it on and off, you know, in the second quarter. By the way, I bet on Minnesota today. I thought Minnesota was going to show up big time. Scott Foster was there, the extender. I was just like, all right, this is all the makings of, whoa. I can't believe Minnesota tied the series. And in the second quarter they kept getting it to one point, two point. And okc, they, they do that thing they do. They get a stop, they get a basket, they get turnover, they get a basket, they get another stop back and then it's a nine point game. You're like, what just happened? I was just talking myself into, into Minnesota being up at halftime and now they're down 10. What just happened? And I think OKC has more of those than any team I can remember. You know, there's been some great defenses over the years and I still feel like the 90, the 90, the early 90s bulls and the 96 bulls and the 89 pistons, there were some, the 04P amazing this team has a really weird gear where all of a sudden they can go on an 8, 0100 run. And it feels like a fluke as it's happening. It's like, ah, that was a dumb pass. Ah, I can't believe he dribbled it off his foot like that.

[Jon Stewart]

They.

[Bill Simmons]

They forced these teams to have the dumbest turnovers. Teams are throwing terrible entry pad. There was a play, There was a sequence today where they tried to get the ball to Randall twice. One time, defense central just. Just misses him by five feet. It was like an intercepted pass, like in football. And then the other time, he almost throws it away again. Like, teams can't even throw entry passes against these dudes. So the relentlessness of them is. Is really something else. And, you know, if they ended up sweeping the Timberwolves, that's usually a good sign for the Finals too. In the last 10 years, the only team there are five teams that had conference finals sweeps. Only the 2018 warriors didn't go on to win the finals. And that Clay gets hurt, Durant gets hurt. That was a stupid year for Minnesota. My only note, other than it feels like Randall got broken over the last three halves, not a good sign for them. And the fact that Nas Reed can't hit threes anymore, for whatever reason, they missed a bunch of corner threes. I actually liked how patient Minnesota was today. And they just kept missing, like, those get over the hump. Rally threes from the corners. My biggest note for them, it's round three of the playoffs and you have an older team that's really physical. Where's the physicality? Why aren't you trying to bang this team around? Why aren't you trying to turn this into, like an 80s type of series? There was one play where McDaniel shoved SGA from behind and they, of course they had to review it because God forbid you'd touch anyone. But I was like, why isn't that happening more? Why aren't they talking shit? Where's Ant? Why isn't Ant talking shit? It's almost like he knows OKC is better than him. So the one thing I want to see from them in game three is like, go back to the Minnesota team. I remember that Minnesota team that even against, like, LeBron and the Lakers was talking, talking, talking the whole time. There's a chance Minnesota's just not that good and that they lucked out playing that weird Laker team around one and then Curry gets hurt in round two. Can't be ruled out. It did feel like they Found something late with Ant and Reed and McDaniels and Alexander, Walker and Conley where they basically just put Gobert and Randle, took them out and tried to match athletes with them. But that's not going to work for four quarters. They have to get Gobert going. They have to figure out how to get Randall into that 20 to 25 points again. But you know, again this goes back to OKC as an answer for everything. They'll just put Lou Dord on you. They'll just put Caruso on you. It just doesn't seem to matter. I still feel like the Clippers in the west were the team that matched up the best with okc. And you know, I, this is the going to be the playoffs that we look back and we're like, man, the playoffs were drunk that year. There were so many weird, crazy games. And one of them was at OkC. I'm sorry, the Clippers Denver game four that I went to, that I keep mentioning, that ended with the Gordon alley dunk. And I still feel like the Clippers win that game. They're in the next round. And I think the Clippers, okc, that would have been the best chance. I think anyone in the west would have had a beating them. And this is a conference that just had Denver take them the seventh. I think Indiana does have a chance. I don't think the Knicks with, you know, basically seven guys, with the way that OKC would be able to just throw everybody at Brunson, they'd be able to attack Towns. I think it would be really hard for the Knicks on both ends in a seven game series against them. Indiana probably not easy either, but at least they could do the offense, you know, the run and shoot, try to try to mess them up and you know, maybe it's Indiana's playoffs. They've had three of the greatest comebacks in the history of the league. They had the single best comeback win I've ever seen. I tweeted it right afterwards not knowing that. What was it? One out of. It was the first out of 977 playoff games where somebody came back from that deficit with three minutes left. It felt that way. Watching it. I was like, I'm pretty sure I've never seen anything like this before. It's the Neesmith game. It's the Halliburton, the bounce, only the Kawhi against Philly. I think a ball has ever bounced that high and gone in. In a key moment, Halliburton gives the choke sign. But then it's going to overtime. And it seems like that is the biggest oh my God, that's going to come back to haunt him. Didn't come back to haunt him. And then, you know, the other legacy of that game is how nervous the Knicks fans got. You can't blame them. They haven't won A title since 73. But you could feel the nerves coming through the TV on the OG free throws and the towns free throws. So what's Friday night gonna be like? You know, it'll be a drunk, nervous New York crowd. It'll be an Indiana crowd playing with house money. And I'm not sure it's gonna matter because it seems like OKC is just clearly the best team sometimes. That's the way it goes. We'll see. Can they be historically great? Can they finish 84, 17 or 84 and 18? Could they walk among the gods? We're going to find out. Interesting basketball weekend ahead. And speaking of interesting, Jon Stewart is coming up and we talked for 90 minutes and it was fantastic and I can't wait for you to listen to it. We're going to have it right after this break. FanDuel is still your buddy for the NBA playoffs. Right now all customers can get a no sweat same game parlay every weekend when you bet the NBA playoffs. We have Eastern Conference games, Western Conference games. This weekend you can use your little special token on three plus leg same game parlay or same game parlay plus or any playoff game. You'll get bonus bets back if you don't win. So if you're feeling like this weekend the Knicks aren't going to bounce back that the Pacers snatch their soul Bet on the Pacers game two. I'm looking at that Pacers game three. I think with the over maybe on that Sunday Pacers win over, maybe throw in a couple Halberton threes. Whatever you want to do, you come up with your own same game parlay. There's no better place to bet it than America's number one sportsbook. Visit FanDuel.com BSGhettyNoSweat same game parlay every weekend of the NBA playoffs. FanDuel official sports betting partner of the NBA. You must be 21 plus in President select states or 18 plus in President in D.C. optum required minimum three leg parlay required refund issued as non withdrawable bonus bets that expire seven days after receipt. Max refund $5 unless otherwise specified. Restrictions apply including token expiration. See [e-mail] gaming problem call Winning Hundred Gamble. Visit rg-help.com. this episode is brought to you by Degree Original Cool Rush Deodorant. Remember last year people got really mad when Degree changed their Cool Rush formula. One dude even started a petition. What was up with that guy? Well, guess what? ° listened. They admitted they messed up. They're bringing back the original Cool Rush scent. And thank God. You've got to love when a brand can own its mistakes. And it's in Walmart, Target and other stores right now for under $4. Grab some, find out why it's been the number one men's antiperspirant for the last decade. By the way, you should put that on especially. We're about to hit the summer. It's getting sweaty in the summers. The original Degree Cool Rush is back and it smells like victory for all of us. Are we taping this on Thursday morning? Sadly, we agreed to do this well before Knicks Pacers game one. Jon Stewart is here. I didn't know if you were going to cancel. I don't know if you want.

[Jon Stewart]

Sam, what do you want? Why are you bothering me?

[Bill Simmons]

You were so happy like a week ago.

[Jon Stewart]

That's. This is, this is the power of the playoffs. This is, this is how it goes. This is the elation, the joy of each victory with the knowing knowledge of you're about to be emotionally thrown over a cliff. And it's.

[Bill Simmons]

Man, but you didn't go last night. You sent your son. Who, who?

[Jon Stewart]

He went. He went with his boys.

[Bill Simmons]

He's. Is he a blank slate for playoff disappointment? Because it's been so bad? Like how. What is his history?

[Jon Stewart]

His history is so. Listen, I've thrown him down on Mets, Giants, Rangers and, and the Knicks. So he's actually not faced the like, like I was trying to explain him. Like this is not even the most catastrophic loss that we've faced in the playoffs at the hands of the Pacers. Like this isn't even, you know, you, you've got to understand like the 90s was just this. Because we were good in the 90s, the Knicks were really good in the 90s, but just could never overcome either, you know, Jordan's greatness or Hakeem lajuan's greatness or just Reggie Miller's pain in the acid ness or, you know, but we face the Pacers like six times.

[Bill Simmons]

Yeah.

[Jon Stewart]

In the nine. Seven times in. And lost in like crazy ways. Like, like Patrick Ewing, a seven foot one with a, I think a 28 foot wingspan, missing a finger roll.

[Bill Simmons]

Right.

[Jon Stewart]

Like game seven. Like you just literally he could have just, just Dunked it. He decided. Let me just see, let me see if it'll bounce off the back of the rim.

[Bill Simmons]

But it all, it all circled back with the four point shot and the, the worst call in the history of the playoffs. What worst call? The seven second continuation.

[Jon Stewart]

Yeah. Larry Johnson. Let me tell you something about Larry Johnson that was. As a matter of fact and I'm glad that you brought this up because it's important for us to discuss this. Larry Johnson suffered at the hands of that and won. And I'm glad that he got the call because he was a fragile flower. You know that Larry Johnson had a very bad back.

[Bill Simmons]

Right.

[Jon Stewart]

And for any of those players to put his vertebrate in jeopardy like that, I thought was, I actually thought it should have been a flagrant two and an ejection like when Starks and headbutted Reggie Miller. Do you remember that? Oh yeah, Starks, Stark. I think it was game, Game three. It might have been, yeah. Game three. Knicks were up. Starks headbutts Reggie Miller and then Indiana goes on like a 30 to 10 run, runs away with it.

[Bill Simmons]

Reggie Miller goed him into it.

[Jon Stewart]

Oh Jesus. Yeah, it's, it's non stop. I mean but I, I have to tell you like.

[Bill Simmons]

So he doesn't know it. Your son wasn't there. Your son's what, 21, 22.

[Jon Stewart]

He's 20 years old.

[Bill Simmons]

Yeah.

[Jon Stewart]

And so. But he's in, he's as passionate about it as I am.

[Bill Simmons]

Yeah.

[Jon Stewart]

And loves. I've got pictures of him, you know, at the games with his spongebob backpack and his, you know, he's five years.

[Bill Simmons]

Old like pointing at Eddie Curry and Zach Randolph wondering why they're starting two big.

[Jon Stewart]

It kept, he kept saying. So they've taken Rick Mahorn's ass and they put it on these two players but they, they don't have the rebounding ability of a Mahorn. They just have the ass. But yeah, so he, he just loves it. And he's got a pretty good. Being raised as a Nick and Matt and Giant and, and Ranger fan, he's got a pretty good tolerance for the beat down. He's got a pretty good tolerance for the raised expectation followed by crushing disappointment. I've raised, I've raised him right.

[Bill Simmons]

Well the Giants piece of it. It was at least the one nice thing you did because like I have a couple friends who are seven Jets. I know but the Knicks Mets jets combo is almost like you're in many ways the spiral of hell.

[Jon Stewart]

Can I tell you something? And this, this Is true. There are states that will take away your children for that there are. That they will bring in child abuse, they will bring in Dyfus if, if you go down that route for, for, for too long. But the nice part about it is he always has like his excitement around the draft or things like that. Like there really is a. Because there are so many sports teams here and it is really a non stop, you know. And I'm always listening to the fan or you know what. So whenever we're in the car, he just sits back and laugh at like Joey from, you know, Queens or you know, Frankie from Iceland. Like what are they? Right? So he loves that shit.

[Bill Simmons]

So I had some. I talked to a bunch of Nick fans last night and today, some of whom were there.

[Jon Stewart]

Are you on a crisis hotline? Is that what you're just.

[Bill Simmons]

A lot of people reach out to me. I'm like a sports therapist. A friend of mine said bad man. A friend of mine said the Charles Smith game is still the nadir and that nothing has will ever compare to walking out. First of all, the vibe at the end of the game and then this complete silence leaving the arena, he said was unparalleled. That that was number one. That's always going to be number one.

[Jon Stewart]

The Charles Smith game was the most excruciating, let's say 7.3 seconds of a Knicks like, you know, because there were so many opportunities there for him to just, you know, I think he had three offensive rebounds in that sequence. Something crazy.

[Bill Simmons]

Might have gotten fouled at least twice.

[Jon Stewart]

But that was back when they didn't qualify. I mean you, you look at the scores of these games and that, you know, like they beat them down 82 to 71. It was the highest scoring game. And you know, I mean these games were Reggie Miller. That was the shocking part about some of the Reggie Miller performances is you'd see a game where it was like 82, 76 and Reggie Miller would score 25 points in the last quarter. Like he would go off in a way that was just like now, you know, there are these guys that are pouring in 40 points, 30, you know, last night, Brunson Cat, you know, Nesmith putting up, I don't know, threes out of nowhere.

[Bill Simmons]

He had eight threes.

[Jon Stewart]

Eight threes out of what? Nine. Something crazy.

[Bill Simmons]

Well, that's what's different now is these heat check guys don't have to be Reggie Miller anymore. They can be Nisma just going bonkers for a half hour.

[Jon Stewart]

Didn't you have Nism? Wasn't he your guy? We.

[Bill Simmons]

We traded him in the. We trade him in the Brogdon trade when got Malcolm Bradley paid off.

[Jon Stewart]

Oh, well, that. There you go.

[Bill Simmons]

Well, he turned into Drew Holiday, which turned into a title, so we. We still somehow considered a win. But you.

[Jon Stewart]

I don't even want to talk to you. You. Like, here's the thing. If you were a Knick fan, you wouldn't even be able to still talk to me right now after what you went through with the Celtics. But you have that 16 championships that have stocked up. You have a resilience in your body. New England has been on the most outrageous championship run that will sustain you. You're like camels that have just come out of illness.

[Bill Simmons]

Like, I got Covid early, but then now. Now my system can fight it.

[Jon Stewart]

You're like. You know what you are? You're like Sherpas at Everest. Like, you don't actually even need the oxygen. You just go up there and you climb up, and it doesn't even fucking matter.

[Bill Simmons]

Well, I will tell you this. When they lost the first two Knicks games, I did not feel that way. Cause that was a. That was a double choke job, being up 20 in the fourth quarter of.

[Jon Stewart]

Two games in a row.

[Bill Simmons]

It's. And.

[Jon Stewart]

But once you've won the championship the year before, like, at a certain point, you. You go like, oh, you know what? Hey, that was a. That was a terrible thing. But, hey, we won the championship last year. That's what I'm saying. You have a. A food reserve. Like, we've been starving. Dude, we won in 73. I'm 62 years old. We won when I was 10, 11 years old.

[Bill Simmons]

Have the picture over your head of. Of the big four there?

[Jon Stewart]

Yeah, big five.

[Bill Simmons]

Four or five? I can.

[Jon Stewart]

That's five.

[Bill Simmons]

It's five.

[Jon Stewart]

You can't see because of the little block there. But it's Willis Reed, Dave DeBusscher, Bill Bradley, Walt Frazier, and then Dickie Barnett, who just passed away, actually. And that's them in the locker room after, I think the first championship that might be.

[Bill Simmons]

So when did you have enough juice to start getting Knicks tickets? Like, when you had the MTV show? When did you start.

[Jon Stewart]

Yeah, yeah.

[Bill Simmons]

When did you become a regular?

[Jon Stewart]

Oh, I was a regular before that, but not in the good seats. But once I started having a chance to get into the good seats, well, then you're. You just try not to pull the card too often, you know, so. But back in. In when this was first happening, they weren't great. So it wasn't until Melo got there and Stoudemire, that you even had competition.

[Bill Simmons]

Like, so in the 90s, you could just get them.

[Jon Stewart]

Oh, no, no, no. 90s. I didn't have 90s. I didn't have the juice. I didn't have the juice. No. I could get the occasional. Like, what I had the juice for in the 90s, not even after the faculty. Like, that's. That's hardcore. That's. I didn't think he'd go after the acting career this soon. That's. I thought we were. I'm coming off a loss. I'm coming off a terrible playoff loss, and I should be received with a certain tlc, a certain kind of. And graciousness.

[Bill Simmons]

You did die halfway through from Turned into an Alien.

[Jon Stewart]

Did I die or did I in the closing credits, in the bonus credit scenes, come back miraculously with a patch over my eye and a thumb bandage. That was the one. I could never. I always asked Robert Rodriguez. I go, let me get this straight. How do I come back? Like, didn't that dude, like, fucking put a pen through my eye and left.

[Bill Simmons]

The lower half of my body and turned into an alien and lost my.

[Jon Stewart]

Eye, the whole thing. And Robert's like, that'd be funny.

[Bill Simmons]

All right.

[Jon Stewart]

We don't have to have a, you know, it's a sea creature that, you know, comes to life in a swimming pool and turns people into, you know.

[Bill Simmons]

Defends your acting career.

[Jon Stewart]

Who's that? Should be nobody, but go ahead.

[Bill Simmons]

No, our beloved. Our beloved James.

[Jon Stewart]

Baby doll.

[Bill Simmons]

Dixon.

[Jon Stewart]

James. Dixon. James.

[Bill Simmons]

We. We were going through it, and when we were at Augusta, and first of all, playing by heart was good, and you were good in it.

[Jon Stewart]

Are we really going to go through the.

[Bill Simmons]

No, we were going through. And he was like, baby John. John could have been. If he wanted to go that route. He, you know, he goes in a.

[Jon Stewart]

Medium baby doll mode. Yeah. He couldn't have. Jon couldn't have. Here's the thing about James, and it's very lovely of him to try and defend it, but he's probably being contrarian. When I was first starting, because, you know, James and I worked together for the whole time. James and I met in, like, 87, 88. He was working in a mail room, and I was still bartending at fucking Panchito's down on McDougal street and just doing gigs at, like, the Bitter End and all this other stuff. So we've been working together since then. So he would, as a, like, Junior, Junior guy every now and again, get a little you know, a blurb off of like Back Page and send me off to a commercial audition. And I went to one and I come back and usually like, you know, you'd hear something. So I think I called him up a couple days later. I go, hey, man, did you hear anything about that commercial audition? And he goes, oh, yeah, I don't know what you did in there, but they hated you. And I was like, what? They were like, yeah, I don't, I don't. I think they thought like, you couldn't act. I don't know if you need to take like lessons or anything. And I was just like, you're my guy, I'm staying with you forever.

[Bill Simmons]

So you like the bluntness.

[Jon Stewart]

Hey, dude, we're in a business where nobody tells you the fucking truth. So to have a guy that will be like, hey, I think that might have sucked is the most valuable thing to have in this industry. To have somebody that'll look at you steely eyed and tell you when you suck is the greatest thing. And because it can be a business of self delusion, you know, and you always try and do that with comedy too. How many times have you met a comic who come off stage and be like, I crushed that. And you're like, I don't know if that does. I think I heard some. There was some light murmuring, but I don't know if I would call that, you know, but they're just dudes that are just like, I'm invincible. So it was always good to have somebody in your corner like that.

[Bill Simmons]

That was such an interesting era when you're trying to take off as a comic, you know, way pre Internet, it felt like you had a whole class of people that all went on to do all these different things.

[Jon Stewart]

These guys at the, they were all at the comedy. So you're talking about David Tell, Ray Romano, Louis CK, Nick DePaulo, Alan Hay, like, hilarious. Laura Kitelinger, Susie Essman would come by. It was, it was. Colin Quinn was in there, like. And you would watch these folks. You know, I, we'd hang out there all night and. And you're working for nothing. You're working for hummus. You know, if you were on the schedule during the week, it was 15 bucks. On the weekend, I think it was 50, 45 or 50, but mostly. And I was working as a day bartender at Panchito. So, you know, Panchito's like a Mexican place.

[Bill Simmons]

What was it?

[Jon Stewart]

What? No, it was an Indian restaurant. Yeah, it looked Panchito.

[Bill Simmons]

I don't know if It's a guy named Bob Panchito who's some Knicks fan. It's a sports.

[Jon Stewart]

There was a guy named Bob. Actually. That was. That was a nice. Yeah, it was this really like early on, blender drink, Mexican restaurant, not a chain. You know, imagine like some margaritas, frozen.

[Bill Simmons]

Margaritas, all that stuff.

[Jon Stewart]

Dude, every learning being a bartender, there was a nightmare. You had like a 3, 4, 5 page, just frozen drinks. They'd like a Creamsicle and a Greenwich blend, you know, and you're just. But as the day bartender, I don't have. You've been a day bartender in a restaurant, but nobody comes in. You're the prep guy. So you spend your day cutting limes so that the night guy can fucking clean up. That's your role. Like, because you couldn't be the night.

[Bill Simmons]

Guy because you're a comic.

[Jon Stewart]

Because I'm a comic. So I couldn't make the money. I could only make the drinks for the night guy to make the money. And then I'd go work for hummus. It was abuser. And I have to say, happy as I've ever been. Just loved it, loved it, loved it. Imagine that you're fucking 24, 25 years old, you're in Greenwich Village. I'm living down near Canal street, you know, sharing a room with a dude. I live in a little loft bed. He lives on the bottom of it. And you're living this bananas dream that nobody ever thought you would ever do. It's not like I was destined for greatness. It's not like people were like, that kid's got was a ridiculous whim. And so to just head up there, no plan, no idea of where this thing was going to go. I worked in catering kitchens and bartended and all kinds of other odd stuff. And just the ability to like walk home at three in the morning through Greenwich Village, in Soho, to get down to Canal street after sitting around with a tell and. And Quinn and those guys. Like, come on.

[Bill Simmons]

So you go, you go to New York and you're basically like, I'm gonna try to figure out how to be a comic, right? And you're just putting it together on the fly.

[Jon Stewart]

Six week lease in an apartment I would see.

[Bill Simmons]

Jesus.

[Jon Stewart]

I used to work in bars down in Jersey when I first got out of college. And I was working at this one place called City Gardens. And it was like a legendary punk club in Trenton, New Jersey. And when I say like Bad Brains, Black Flag, Suicidal Tendencies, Misfits, like all the great punk bands of that era would Roll through between New York and Philly. So Trenton, it was this weird shithole, like a warehouse, you know, in the middle of, like, this very kind of dangerous place. It was a very dangerous place. And. But all the bands that would come through, I'd get to interact with, because the bartender, you're up in the green room. You know, you're bringing them beers and booze. And so you're. You might not remember this. You might be too young, but do you remember Martha Quinn of mtv?

[Bill Simmons]

Of course.

[Jon Stewart]

Oh, okay. So she was everybody's pixie. Everybody.

[Bill Simmons]

I was only child. I remember every. Every moment of mtv.

[Jon Stewart]

So she was everybody's pixie and adorable thing. Well, there was a band called Stiff Baders and the Lords of the New Church. And Stiff Baders was the lead singer of Lords of the New Church. He's on stage. He's an addict. Opiates, heroin, whatever. He's on stage. He's sick as a dog. So he's. He's vomiting. He looks like we need to get him that. You know, this is before they would do IV treatments, like, for, like, hydrate people. So he looks dehydrated, near death. I go upstairs to the green room after the show. He's lying there kind of sort of comatose. And I'm bringing booze in for everybody. And Martha Quinn is in there on his lap, and he kind of revives every now and then and is making out with her. And I was like, boy, this industry is really. It's not what it appears to be. On television, it might be a little darker than what I had originally surmised. Yeah. Oh, my God, it was a wild place. But it inspired me because I talked to these guys and they'd be like, what do you do? And I'd be like, I get you drinks. And they're like, is that it? And I'm like, kind of. And it. It. I always had this idea in my head, like, I wanted to try to be a comic or be a writer or some shit. And they were like, so, what do you do? Why don't you do it? And it. It kind of propelled me to. One day I just sold all my shit and got a U haul, drove up to the city, and that was it.

[Bill Simmons]

Well, it probably made you realize how haphazard everything is and that you think in your head when you're growing up, oh, there's this whole process and you gotta do this and this, and then you get this. And then you realize, like, oh, yeah, maybe you just throw caution in the wind for Six months, and it might work out, it might not.

[Jon Stewart]

Right? You just make decisions. And I remember telling people, and they were just like, what? Like, it's one of those things. They were like, I don't think that. I don't think any part of that sentence that you just said makes sense. Like, I'm Le. I'm leaving and, you know, going to go to New York to be a comic. And they'll be like, what? But it was. It was a.

[Bill Simmons]

It was a ball in the late 80s. The best case scenario for being a comic is maybe you get a 12:30 show someday. Maybe you get to tour the country. Like, what in your head, who's your role model? Like, signify the country. Yeah.

[Jon Stewart]

Well, no, those guys were so far above and beyond.

[Bill Simmons]

Look, but I mean, like, if you're shooting for the stars, who are you looking at?

[Jon Stewart]

That's the thing. I wasn't shooting for the stars.

[Bill Simmons]

Right?

[Jon Stewart]

Like, I wasn't thinking like that. I think maybe that was partially how I was able to kind of endure whatever indignities get thrown your way. Like, how many times can you go to Carlos in the kitchen of panchitos and go, hey, man, any chance you could make me, like, dinner and then maybe a breakfast, too, that I could put in a tin and just take with me? Like, it's a lot of indignity. You know, you're. I'm a grown man at that time. Like, I'm not. I'm not a. I'm sharing a room. Like, when was the last I shared a room when I was a kid? Like, when was the last time you shared a room? You know, I'm. I'm in a. I know how to drive. I'm old enough to drink, and I'm sharing a room with the dude. Like, it was. You know, you did. I didn't think, oh, man, I'm gonna do my own. They're gonna discover me like they discovered Seinfeld and Roseanne, and it's gonna be. And you're on. It was. I hope I get good enough to pass the club. Like, there were milestones, but the milestones were much closer to your face than what you would imagine. You know, I imagine for you, sort of assimilate. Like, you think to yourself, I'm going to create a podcasting network and a conglomerate of writers and sports. You know, you don't. You think, like, how am I going to get good at this? How am I going to get good enough at this that they'll let me work here for the $15 I might be able to get Holy. How do I get here? So they'll let me work on the weekend. Like, that's where, like, they put cash money in your pocket. Like, if you could do five sets at different clubs on a Friday night, six sets. Attel was the king of that. Attel was. He would do like nine or ten sets in a night. Like, really? Oh, my God. The most industrious. Like, you would barely see him. He'd wander in real quick with the cigarette dangling, go up on stage, bang out 20 minutes of fucking hilarity, pop into the subway right uptown. Cause you had to go the circuit was the Cellar, downtown Boston, comedy. But you also had comic strip, catch a rising star uptown, Stand up New York. Although they did like weekend bookings. So you had a bunch of places, but you had to travel. Caroline's at the Seaport, then in Midtown. So it was like a little troubadours.

[Bill Simmons]

How long did it take you to get good at it?

[Jon Stewart]

I'll let you know when I get good at it.

[Bill Simmons]

Well, when did you feel like? Okay, I actually feel like I somewhat know what I'm doing here.

[Jon Stewart]

I think it was. And I wouldn't know the dates. I can tell you. The process of it was I worked at the Cellar, which was just a few doors down from that bar I was working at. And this guy, Bill Grundfest and Rick Chrome, who sort of ran it and booked it, let me hang out there every night. Not obviously on the weekends, where the real comics were. And they would put me on every night as the last guy. So Sunday to Thursday, I'd go on at 1 in the morning, 2:30 in the morning, depending on the comedy seller back then wasn't what. What. You know, it as today, which is like Monday night they're doing three sold out shows for, you know, and packing it in. And it's all just, yeah, really great, really established comments. Like, best shows you would ever see in your life. And then even in the middle of it, Chris Rock will show up and like, bang out a set. You know, crazy stuff.

[Bill Simmons]

Yeah.

[Jon Stewart]

So, you know, they would put me on every night. And you learn how to be yourself. You learn how to be yourself on stage, which is the only way you can create a kind of sustaining comedy career. And I remember doing that. And you do reps. You know what it felt like being like a gym rat, a comedy gym rat. And it was you and the waitstaff and the occasional table of like, drunk Norwegian sailors or whoever might wander down there because the place wasn't packed yeah. It's not like they started the show at 8 and they ran it till the last person left.

[Bill Simmons]

And I was the guy reps in.

[Jon Stewart]

Getting your reps in. And that's when I started to feel like I figured it out in a way that didn't feel embarrassing if that's.

[Bill Simmons]

Well, plus, you're allowed to make mistakes. Like, I look back when I had my comms before I got to espn, I was on my own for four years just writing comms. And some of them are good, some of them are bad. I'm making a ton of. But I was able to make these mistakes with not a big audience. Right. And then you learn from that. And then by the time you get the audience right, you have enough of a feel of what's going to work and not work. So I was so frustrated those four years. Like, is this ever going to happen? Should I go into real estate? What should I do? But then you look back and you're like, oh, that's actually really good. It played out this way that I spent that much time trying to figure out how to get good at something, because then when it happened, I was ready for it.

[Jon Stewart]

You were in column college. It's an essential learning experience, but that's also what you have to want. It sounds like you wanted to be a writer.

[Bill Simmons]

Yeah.

[Jon Stewart]

Not. Not a star. And the people that I always really loved were the people that wanted to be comics, not stars. They might get good enough to be. Like, the way I sort of looked at it was, if I get good enough, it'll be like bartending, like something you can make enough money with that you'll be okay.

[Bill Simmons]

Right.

[Jon Stewart]

And then occasionally people would show up. Like, I remember when Chappelle showed up. I mean, he was like, every now and again, somebody would come in that's just built different. Like, a lot of us are, you know, you're. You're in there doing your work a day sets and trying to make your way and kind of build, and then a kid will come in and you just go, oh, well, that's just touched by God. That's just a different. That's just a weirdly different prodigy.

[Bill Simmons]

Yeah.

[Jon Stewart]

And I always felt good at not feeling mad about that. I remember seeing Dave and just going like, I love that. I love that that kid can do that. Rather than feeling like, why is that guy so good?

[Bill Simmons]

I was being threatened by it, right.

[Jon Stewart]

Because I watched a lot of guys where bitterness stole whatever shot they had. Like, I always tried to maintain that feeling of no matter. Like, people say like, when did you think you made it? And I'm like, here's when I made it. When I left Trenton, that's when I made it. Like, everything else is gravy. Like, you. You tried the thing. Like, that's all you can give yourself as an opportunity and work your ass off at it. But, like, you always try to maintain that kind of feeling of proud of yourself no matter what happened, because you did the hard thing, which was to cleave yourself from your old life. That was. Would have been fine.

[Bill Simmons]

Well, the funny thing about your industry at the time is you have all these damaged people who are really good at what they do. And a lot of them are just pre. Naturally bitter. There's gonna be bitter anyway and super mad at everybody who's more successful than them. That's part of the comedy industry.

[Jon Stewart]

But I didn't find that to be the general. Like, that was the whole. The reputation of comics is, like, damaged people doing a damaged thing. Like, they were the funniest, smartest, nicest, like, often warmest people you'd ever come across. Like, we all have our shit. But this idea of, like, what's up, sad clown? Masking your pain, like, it didn't feel that way. It felt like people excited to be in this very fertile, creative environment. I mean, we all worked. We wrote for, like, Caroline's Comedy Hour and Comedy Central came on board in the middle of it, and, like, some of us got, like, little jobs there, like. But it felt, you know, I can only imagine, like a creative scene that, if not relevant, was at least, like, it was. It was. It was constructive. It was like, you felt the excitement of it because we were getting to do what we wanted to do. Like, it was a crazy, wonderful, weird, dumb life.

[Bill Simmons]

I think the thing I was always jealous of from afar, you know, when I moved out here to work for Kimmel and he was dating Sarah.

[Jon Stewart]

Right.

[Bill Simmons]

And Sarah had this whole web of people, and it was almost like a sports team.

[Jon Stewart]

Yeah.

[Bill Simmons]

She knew everybody and she was down there. Yeah.

[Jon Stewart]

And she was unbelievably good. Another one that was just young but really fucking good.

[Bill Simmons]

Kind of knew what their voice were. Yeah. But they. The way they all pulled for each other and how they knew everybody and they were all it was. I was like, wow, this is not what I expected from the comedy industry. That it was a little more rowing the same way than on the boat than I.

[Jon Stewart]

You would kind of thought you would get a dick or two, but it was the exception, not the rule. And even the people that you thought, like, wow, that that person's dealing with a lot. They generally didn't take it out on you. You were part of their support, not a part of their attack. So I have nothing but ridiculously fond memories. And I'm sure there's a little gloss of nostalgia that carries over maybe some of the tougher times. But I think if you didn't. If it hadn't been somewhat painful and somewhat of a struggle, I don't think it would mean much in the aftermath if you didn't feel like you had to develop. You know, it's like when you talk to a guitar player and, you know, and they play unbelievable. And then they show you pictures of, like, the blisters on their hands, and you're like, yeah, that's no blister, no solo. You know what I mean? Like, it's.

[Bill Simmons]

It's part of a process from the MTV show. Like, you probably do this show. What did it last, two years? Three years?

[Jon Stewart]

Two, I think. Yeah, something like that.

[Bill Simmons]

And then. Then it's done. You move on to other things. But now we're in this YouTube video era, and all these clips come back from it. And one of the things that's amazing.

[Jon Stewart]

About that, the MTV show.

[Bill Simmons]

Oh, yeah. One of the things that's amazing about it, you had. You had unbelievable music on that show.

[Jon Stewart]

Best part of the show.

[Bill Simmons]

And a lot of these artists, like, that's kind of. It was kind of the prime apex of their careers during this amazing music time.

[Jon Stewart]

We had that was. We had a guy named Bruce Lee Gilmer who was the music Booker, and Beth McCarthy was the director of the show, and she had been a director at mtv, did all the live. Like, if you ever watch Nirvana Unplugged or those kinds of things, Alex Coletti had come up with the conception, was doing the Unplugs, but Beth was directing them all, you know. And you see, even in that Nirvana Unplugged, that little moment where, like, Kurt turns and smiles to the camera, that was Beth going, like, are you having fun here, Kurt? At all? Like. But she's, to my mind, like, the greatest live music director of all time. Like, she's just phenomenal. She went on. She did, you know, Saturday Night Live, but she directed our show, our dopey little show for the whole time it was on. She was.

[Bill Simmons]

It's the peak of alternative.

[Jon Stewart]

That's right.

[Bill Simmons]

Hip hop's coming super hard at that point.

[Jon Stewart]

Yep.

[Bill Simmons]

Just. Oh, everything is. Everything is humming in 93 and 94.

[Jon Stewart]

When we were done at MTV, we went over to Paramount, and I think the first week on the air, the musical guests were Public Enemy and Johnny Cash. And, like, that was the breath of it. Biggie Smalls was on odb, Wu Tang, Mike Watt came on and Grohl played drums while Eddie Vedder and Pat Smear played guitar for him. Like, it was insane. Slayer, Danzig, like, it was the breath of it. Baby played Mother.

[Bill Simmons]

Now, that was somebody who knew what his Persona was.

[Jon Stewart]

Yeah. No, I love those guys. And they were all like, again, like, I know the reputation. Like, oh, everybody comes on and there's attitude and all that shit. None of it. Like, they were all hanging out in the green room with, you know, Trent Reznor and Marilyn Manson. Like, it was crazy and it was so much fun, but the music was so good and such an important part of it. And, like, were able to sneak in, you know, Guided by Voices and Bad Religion and bands that were, like, not quite mainstream, but really great. You know, Buffalo Tom. Right.

[Bill Simmons]

Canon Crow were in there. I remember a bunch of them just.

[Jon Stewart]

It was an incredible. That was my favorite part of the. Of the show. Loved it.

[Bill Simmons]

I thought the show. I. I don't know. I thought the show was good. And it had a weirdly important place in pop culture because mtv, that was the height. Mtv, all that shit, you know.

[Jon Stewart]

Who didn't? Well, were the executives that were in charge of the program when they canceled it. No, the MTV one, actually, we did really well in the ratings. It was when we went to Paramount, got syndicated is when. That's when it went.

[Bill Simmons]

I blame that on Baby Doll completely.

[Jon Stewart]

I told them, I said, don't do this.

[Bill Simmons]

No, no. He's like, baby, it's a lot of money. We gotta do this.

[Jon Stewart]

No, it was. What happened was Arsenio left and Paramount owned mtv, and so they bought us.

[Bill Simmons]

Yeah.

[Jon Stewart]

To do that.

[Bill Simmons]

That was it.

[Jon Stewart]

But we didn't realize, like, you'll be on at three in the morning in Houston, at 11 o' clock at night in, you know, Atlanta. But even that was a great experience. And to go to our earlier point, when you get canceled and your name is on the show, like, when they come into the office and go, that show with your name on it.

[Bill Simmons]

Yeah, I've had the experience.

[Jon Stewart]

It's not great, Right? It's not great. But what's better than waking up the next day and going, oh, I'm still alive and I can still write jokes and I can still do the shit that I love to do, and it won't maybe in that venue, but I can Go off and do it. That's the crazy part about, I think, the way that people view the kind of stereotypes of the businesses that we're in. And I heard Jack Antonoff actually sum this up really well. I can't remember the interview I was watching, but Jack Antonoff was talking about going into music, and he would be like, I'm thinking about going into music. And everybody would say to him, like, what are you crazy? Music. What do you think you're doing? But if he had said, I want to be an astronaut, they'd all be like, yes, fantastic. But then he goes, but how many. There's like, seven astronauts. Music is everywhere. Like, why wouldn't they say, oh, you love music. That's amazing. It's everywhere. And that's. They view these careers as, like, not safe.

[Bill Simmons]

Yeah.

[Jon Stewart]

As a lark, as an indulgence. But comedy is everywhere, sports are everywhere, Writing is everywhere. Like, why wouldn't you say to somebody, oh, if that's what you love, you'll probably work your ass off at it and you'll probably end up. You might not get to here, but you might be fine. You might make enough to make a living and have a family. Why wouldn't that be encouraged? I think so, yeah.

[Bill Simmons]

Oh, God, no, no.

[Jon Stewart]

I was just gonna say so that when the cancellation came, as hard as it was, it was also freeing because I realized, like, oh, I still get to do the very thing that I came up here to do.

[Bill Simmons]

Yeah. Well, I think the difference now, the potential of becoming either famous or successful seems easier because we have all these different levers you can pull now. Like, somebody could just start a video podcast on YouTube and actually get an audience pretty fast.

[Jon Stewart]

Oh, yeah, right. And they do that, right?

[Bill Simmons]

Yeah, yeah. Oh, they definitely do. So you. First of all, you can have an audience too soon. Second of all, you have the potential of this could happen to me soon, which I think skews the brain chemistry a little bit, where you're like, right, why isn't this happening yet? It's been three months. And I think what was different about our generation was, was you never. Never really thought it was going to work out. And if it worked out, that would be great. But there was. There was no. It wasn't like there was, like, this prize in the bottom of the Cracker Jack box. You're like, man, I really hope this works out, but I have no idea if it is. Now it feels like it can work out, which I think why people even get more and more frustrated when it doesn't. You Know, yeah, maybe.

[Jon Stewart]

Maybe the key to our generation was a utter lack of confidence.

[Bill Simmons]

That was Gen X and right before Gen X of like, yeah, this actually might not happen.

[Jon Stewart]

There were viral sensations back when we were younger too. It was just a different mentality, you know, it, it. They didn't have the, you know, I'm sure there was a, you know, an analog to Hawk Tua, you know, back in. You know. But, but it would be like Donna.

[Bill Simmons]

Rice or one of those type of people.

[Jon Stewart]

It's Exactly. That's the problem. Perfect analogy to Although. Yeah. Somebody that came up through notoriety and maybe infamy.

[Bill Simmons]

Yeah.

[Jon Stewart]

But didn't necessarily have something attached to that. But then took those opportunities beyond that to go on all kinds of, you know, write a book or be on shows or that kind of shit.

[Bill Simmons]

One of the things as, as we get older and we watch how culture changes. Like one of the things that's so interesting to me is the late night host piece. Like it seems like CBS is just going to dump the 1235 spot that used to be this breeding ground for new comics. Right. It'd be like. Or new hosts or this would be either you put somebody who's established or you put somebody who has a chance to basically become you. And now there's two problems with it. One is the audience is just dwindled to the point that it's like Kimmel and Colbert and. And Fallon and Seth and maybe those are the last four we're going to have and a network. But then the other piece is if you're going to try to get somebody young, up and coming, is that even a good move for them? In the same way, are they just better off being on the road going around? Like I would think those people would rather be Nate Bargazzi who may. Who's now doing basketball ratings. That's the issue.

[Jon Stewart]

Right. I think those people would rather be the biggest comic in the country. That's not really how it.

[Bill Simmons]

But 10 years ago, Nate Bargazi or five years ago probably gets the 12:30 thing over having happened what happened to him. Right. Because the old model happens. You know what I mean?

[Jon Stewart]

Or a sitcom or something along those lines or other things.

[Bill Simmons]

But now you're just better off going to the people and going on tour.

[Jon Stewart]

Some of that is just ubiquity. Right. So people don't. Those sort of talk shows do provide, I think, a kind of weird repetitive habit forming. Like I go to bed watching the Tonight show or Colbert or Kimmel and I wake up watching GMA or the Today's you know, that's always been kind of the, the idea of it is to lock people into a brand. I'm. I have a CBS lifestyle. I have an NBC lifestyle, you know, and if you want, if you look on YouTube, there's still millions and millions of people. You know, the ratings traditionally are maybe not the same, but I would argue the reach of it is maybe bigger. It may not be monetized through advertising dollars in the way that they think makes it an efficient use of network capital, but in terms of its ability to permeate and people to see it, I think is still really, really large.

[Bill Simmons]

It shifted to YouTube and Spotify and.

[Jon Stewart]

You look at Seth will do a bit of, you know, on it's 12:30 at night, which was never like a huge audience thing, but he'll get millions of people watching it on YouTube or Facebook or whatever the hell people watch stuff. Now Mulaney's doing a cool thing on Netflix. Like, yeah, just allowing himself like to do to. To just be as creative as like old time Letterman on a weekly basis on Netflix. They've given him kind of the leeway to be able to do all that stuff. I think what will ultimately happen is you'll still have something that resembles it, but maybe not with the infrastructure where we're carrying old. Yeah, like the way I look at it is like I run a Tower Records. Do you know what I mean? Like, people are always going to want music, right? And. But I'm still the guy who's like, well, come into my giant building and let me show you the new CD rack. Like I'm. It's just a delivery system of something that I think people will always find somewhat interesting or appealing. But without the brick and mortar like you watch Z Way or somebody who's doing something really interesting. Creativity finds a way like great, funny, interesting people find a way to make topical commentary or interviewing interesting for, for people. And that's, that's always going to be something that I think will have appeal. It just may not have an appeal with 250 employees in a giant theater.

[Bill Simmons]

Right. With people coming every day. Yeah.

[Jon Stewart]

Right.

[Bill Simmons]

Well, it's interesting with you. You're just doing Mondays now, right?

[Jon Stewart]

God bless. That's.

[Bill Simmons]

And your show and you on that show still feels like it has the same impact. But you're not having to do the, you know, you're not pitching every day.

[Jon Stewart]

You're pitching.

[Bill Simmons]

You're now starter. You're not, you know, you're not throwing the 120 innings.

[Jon Stewart]

I come back in I do that thing now that, like, Aaron Rodgers can do, like, where you do the thing where you're like, I'm going to go on a darkness retreat and. And then maybe I'll sign in September, but I don't want to go to practice. Is that okay with everybody? You know, it's that kind of shit.

[Bill Simmons]

Did you worry. I mean, obviously, you know what you're doing, but you hadn't done that show, and then you're doing that first show we did.

[Jon Stewart]

Were you.

[Bill Simmons]

Were you nervous or did nervous energy? Like, what was it. What was it like to just do it again?

[Jon Stewart]

Well, look, the muscle memory. I think one of the advantages I had is the people that. The really talented creative writers, producers and all that of that, you know, it's. It's a. It's an organism. It's a mechanism. And the people that did it when I was there were still there, only they had all leveled up their skills. Like, they had all done boss battles. And so now I was walking back into the place where it was the comfort of all these people. I love. Like, I will say we have a fucking ball. Like, I know that. That's. I think everybody works hard, but it is fun. Like, they're great people. I love being around them. They've leveled up their skill level. So that part I wasn't nervous about. I was. Man, it's a weird. It's hard to describe the feeling. The first day I went in to do the show, and I'm sitting behind the desk in rehearsal and. And a lot of the camera guys, this guy Phil, this TQ And Richie, they're all behind the cameras. It's like, people that, you know, I've been with for 30 years, so I knew them all. So it's not like I was like, where am I? Who are you? You know, the comfort was there. We did the rehearsal, but when I put the suit on and I came down and I sat behind the desk in the suit and I looked into the camera and saw on the monitor myself at the desk in the suit with the script, had the pen, the whole deal. But I look like this now.

[Bill Simmons]

But you're older.

[Jon Stewart]

Yeah, it looked like. Do you know those, like, Instagram posts where they're like a friend group that takes the same picture every 10 years?

[Bill Simmons]

And, like, there's that one year where everybody looks old all of a sudden, right? Yeah.

[Jon Stewart]

And that was daunting because it was a very strange, like, kind of melancholy feeling of the evidence of, you know, decrepitude is too strong a word. But you do look at that and think, oh, like Pat, it was explicit evidence of passage of time.

[Bill Simmons]

Well, that's the, that's the phenomenon of, like high school graduations, college graduations, weddings. When, Right when we were younger and we'd watch the parents crying and be like this, idiots. Why are they, what are they so upset about? But then you get it as you.

[Jon Stewart]

Get older, like, and as your kids get older. And so as I sat there, it really was a stark feeling for me and also wondering if the audience would be able to get past it to just hear the jokes and see all the thing, or if they would be distracted by this image that they had seen for so many years that was now so clearly in a different age demographic.

[Bill Simmons]

But you were out there. It wasn't like people hadn't seen you in seven years, right?

[Jon Stewart]

Not much, man. I, I'd been out there a bit. I'd been on Steven's show a bit, but I, I really don't. As you know, James will tell you, I don't like to do shit. I like to be home.

[Bill Simmons]

And not only will he tell you it, it drives him crazy. He just feels like you're costing him money constantly. It's like four more country clubs he could belong to.

[Jon Stewart]

Oh, my God, that's so funny. Listen, I put enough, I put enough distance on his pool that I feel very comfortable with the choices.

[Bill Simmons]

Do you realize what John could do? Do you realize if he just committed for one year what we could do?

[Jon Stewart]

He'll tell you the worst ones are the advertisements, the commercials. People would come with and he'd be like, what that you don't understand. This is. They don't make deals like this. And I'd be like, I don't care. I don't, I don't use that product.

[Bill Simmons]

Well. He just wants enough that he can brag about how much he helped you. He has and the great deals that he gets. All he wants to do is brag about the deal.

[Jon Stewart]

He got the best at what he does of anybody I've ever seen. And part of it is he's so. He doesn't play games. There's no bolt. Like, he's just like, this is what we're doing. He doesn't try and trick people. He doesn't strategize around it. He doesn't try and take shit shortcuts. He just does his job in a straightforward, like, clear cut, honest manner. And the people that appreciate that are great to do business with. And the people that don't appreciate that are people you wouldn't want to do business with in the first place, because there are, as. As you have probably figured out by now, a shit ton of liars in this business on every level. Yeah.

[Bill Simmons]

And sadly, I have to deal with them on the executive side now. And it's. It's not great, really.

[Jon Stewart]

Part of it is absolutely, I'm sure, not what you got into. What's the part of this that you love the best?

[Bill Simmons]

I think it's elevating people who have something that it could go to another level, and then watching it happen, I think is the most fun part, which I think you've had an incredible amount of experience with, too. Like, you think of the.

[Jon Stewart]

It's pretty great.

[Bill Simmons]

The Daily show tree. When you watch somebody that. And you can watch them go from here to here. And if you have, like, a tiny part of that, I think that's probably the best part.

[Jon Stewart]

Watching people level up, whether as writers or the executive producer of the show, Jen Flance, who's the executive producer show who. Like that show wouldn't happen without her. If you're looking at the special sauce, she's the keeper of the formula to the Krusty Krab. She knows what's up. She was a PA when I got there in 1999. She was. She was in the building before I was. She was a production assistant. And you just watch. She was just a killer. Just smartest shit. And, like, you just watched her get better and better and better and level up and level up and, you know, making her executive producer was the. One of the easiest decisions of my life. Like, it just easy when that.

[Bill Simmons]

That first show you did back, you did all the Biden stuff, and people were surprised that that was your first thing. And it be. Immediately became polarizing. And then we look back and it's like, all right.

[Jon Stewart]

For that show, people were mad.

[Bill Simmons]

Yeah. Really mad at you.

[Jon Stewart]

Yeah.

[Bill Simmons]

Why is he doing this? Why is he. Why is he bringing all this up?

[Jon Stewart]

Called me a threat to democracy.

[Bill Simmons]

There was a while there, it was like you and Charlamagne, and I don't think anybody else was saying anything.

[Jon Stewart]

Oh, Charlemagne's so. I love listening to him. He just. He just cuts through it.

[Bill Simmons]

But it's just been crazy to watch the last year. And especially you did your show on Monday about Jake Tapper's book when he's on TV the whole time, right. Not saying anything, and then it's like, I've got some news. I thought that was, you know, that's. That's why your show. I Think as long as you want to do it, it's so essential because you're just taking these little things that are happening and then tweaking them and presenting them in a way where you're like, oh, yeah, that's kind of fucked up.

[Jon Stewart]

Well, I think the process is. It continues to be sort of what it always was, which is. It's not a reexamination of news. It's really a kind of reexamination of the most. What you think are the most absurd aspects of these institutions that we like. To me, that first Biden bit we did was that. Yeah, like, I just. I was watching this with a sense of like, am I insane? Like, the idea that we're not looking at this as that, you know, we are supposedly in the most dangerous election of our lifetime. The only way we will fend off forever fascism, and we're not going to put our best foot forward, and we're going to all pretend that. That this guy who did fine did a good job, but, like, this ain't pee wee football. This is the presidency. And it just seemed utterly absurd to me. And then I remember we had come back. It was right after the Super Bowl, I think. And traditionally, I think during the super bowl, the president has an opportunity to address, you know, do an interview in the middle. So this is the run up to the election. You have a chance to do an interview and get to. And they decided not to do it, but rather put out tiktoks of him eating chocolate chip cookies.

[Bill Simmons]

Right.

[Jon Stewart]

And seems like a red flag. And so we ran a big montage of everybody saying, the idea that he's too old is ridiculous. He's the sharpest guy. You don't. I think it was. You don't understand. If you were in the meetings, you would see someone at the top of their game, sharp as attack. Sharp as attack. And the joke was, ooh, has anyone thought to film that?

[Bill Simmons]

Right?

[Jon Stewart]

Because the shit we're seeing does not engender. Because what happened with Biden, and this sort of brings it around to comedy. Like, the worst thing a comic can be for an audience is fragile. Like, if you're in the audience and you're worried about the comic, not in a mean way, like, in a way of, like, I don't think this guy's very good. This is going to be rough. And he's, like, stumbling. The spell is gone. It's a fragile spell. And if that's the way you're viewing the president, and that is the way when you couldn't deny that when you watched him, there was trepidation that he wouldn't get through it and he would fuck it up.

[Bill Simmons]

Well, the other piece of it was, it was the private conversations we were all having about it weren't being captured in public conversations. And that's always when you know something is off. Because all the conversations I was having was like, what the fuck's going on? He seems seeing Parkinson's, what's happening.

[Jon Stewart]

And that was two years those conversations were taking place everywhere except on the news where they're supposed to take place. And I think, you know, I've always said the truest part of CNN or msnbc, the truest part of the broadcast is in their green room. If you go to the green room of those 24 hours, you'll hear the truth. You'll hear people that are involved in politics, that are politicians, that are consultants, that are journalists, that are analysts. That's where they tell the truth. Can you believe this guy? There's no way he makes it through. He can't even get up that if we do this, it's a disaster on the camera's on, red lights on. You know, I don't. He's able to get through certain legislation. I wouldn't say that it's a detriment. I think it's. Perhaps it's his experience that could help. But if you go in that green room, that's the truth. And our show has always hopefully been a kind of presentation of the absurdity between what's going on in the green room and what's going. What they're putting out as the official version and how those differ.

[Bill Simmons]

Well, ironically that also happens in sports. Cause I even remember, yeah, I remember the first year I did NBA Countdown and Magic was on the show and we'd be in the green room talking about stuff to talk about in the show. And half of the thing was trying to get Magic to say the stuff he said in the green room on tv. But that red light really. Oh yeah, that red light really scares. There's just repercussions with every sentence you say. Especially if you're ad libbing on camera or you're talking for 30 straight seconds and the words are coming out. Sometimes you can't control where the words are going and you're trying to make a point. It's either too harsh and you end up, you end up kind of receding and being more careful. And that's.

[Jon Stewart]

Yeah. As well, you know, shifts in tone. I don't mind. It's shifts in Absolutes that I always mind. And I think, like I've always said to the people at Daily Show, I go look around this room. Like, when you leave here, these will be your only remaining friends. Like, you can't look at it like, yeah, I need to maintain access. And I firmly believe that if you stick to what you think is true and defensible, you'll be okay. We all fuck up, you know, we all say something that's intemperate or like, maybe didn't come out the way you want it to. And when you own that stuff, when you need to, you should. But boy, when we put on this, and you and I are wrestling fans, when you put on this kayfabe.

[Bill Simmons]

Yeah.

[Jon Stewart]

And now I'm starting to feel like the whole thing is kayfabe. The whole thing is, you know, we talked about it on the show. It used to be the. It's not the crime, it's the COVID up. I feel like the whole thing is cover up. Now, no matter who's out there, you're.

[Bill Simmons]

Talking about authenticity, which I think feels in 2025, like the single most important word. Right.

[Jon Stewart]

But they still think of authenticity as a strategy, which is the antithesis of authenticity.

[Bill Simmons]

But that's. I think what's shifting is authenticity, just in the purest form, is now becoming the thing you want. Because we see this with athletes and celebrities, and I think social media has a big part of this. They're presenting this version of themselves or this version of what they should say, how they should act for the public, and you don't really know what's behind it. And then over and over again we find out, oh, that person was a maniac, or, oh, that person got caught, you know, behind the scenes saying this when they actually said this in public. And I, I think a lot of.

[Jon Stewart]

The ways they did the violence, is that intentional? Is. Is that for athletes? Do they have people kind of that. That are working with them on that to make it that way?

[Bill Simmons]

I. I actually think the decision was the. Was kind of the turning point. And then there's social media pieces too. But the, the decision went so bad for LeBron and was such a bad kind of move, and it's kind of just such a bad unforced error, right. That I think it made it reconfigured how people think about when they do something.

[Jon Stewart]

Right.

[Bill Simmons]

Do you. Do you have to think about all the ramifications, good and bad, and then that leads to this weird social media Personas everybody has now that you've known.

[Jon Stewart]

And Then you see somebody, if you look at it and go, well, geez, if somebody who is as great as LeBron can face a backlash, I guess, what chance do I have? I mean, Jordan was very, you know, famously was like, I'm staying out of the fray. And, you know. But then you see the 30 for 30s and, you know, the last dance and all that, and you're like, oh.

[Bill Simmons]

The gambling stuff with him was way worse than I think people remember. I mean, he's. He's giving interviews on the pregame show, like, I do not have a gambling problem. It's like watching politicians.

[Jon Stewart]

Right.

[Bill Simmons]

But now I still think there's some really. I think we have some athletes now that feel authentic to me in everything they do. And you kind of know who they are. We don't have to do the list, but. And then there's some people that still feel like they're trying to present some version of themselves that they think we want versus whatever it actually is, you.

[Jon Stewart]

Know, and it's ultimately, they get called out for it, I think. You know, there's that.

[Bill Simmons]

Right.

[Jon Stewart]

You know, there's always, you know. You know what's interesting, Tatum faces that a lot, which I think is you sort of. You look at a guy who's just so good and won a world championship, but even in the midst of winning a world championship, people were like, that's the wrong way to say. You know, what he just said mimics what Kobe just, you know, And I thought that was so fascinating that here he was at the peak of this, and he clearly, like, with his boy, which, like, you're just like, oh, my God, this is a moment's moment like this. And then you look online, and people are just, that guy. He's doing. That's. That's not real. And you just think, oh, boy. The other thing that I forget, the other piece of it is we face relentless. We live in a. A culture of relentless comment, relentless commentary, and those that are in sports or entertainment or politics, you know, those relentless comments as they exist in the ether, but I think they ultimately begin to have a kind of molecular weight to them as well. That. A heaviness. And you carry that. You carry that around as a little bit of extra weight as you're going through this other journey. That's really hard to do in the first place, especially if you think it's weighed on them.

[Bill Simmons]

Yeah, if you're looking for it, you're in the comments.

[Jon Stewart]

But people say, like, I don't go in the comments. That's nonsense. You Know, I don't. I don't check that stuff. Yes, you do. It's like saying. It's like being. It's like being in a comedy club. Right. And whenever you're in a comedy club and you're doing a show, there's going to be a table of people that, like, aren't having it, just not feeling you.

[Bill Simmons]

Yeah.

[Jon Stewart]

Social media is. Then you have to ride home with that table in the cab and. And hear them talk their. But to suggest that, like, I don't listen to it. Like, people are calling your name. You're not going to go, what? Like, of course you know about it. How can you not?

[Bill Simmons]

Well, there's difference in knowing about it and then obsessing over it. Oh, that's.

[Jon Stewart]

Yes. No question. You have to learn how to.

[Bill Simmons]

I try to avoid as much of it as I possibly can because I think it's. I think it's damaging.

[Jon Stewart]

It's.

[Bill Simmons]

It starts putting.

[Jon Stewart]

That's my.

[Bill Simmons]

You know, it's like being. It's like being in a room in high school and you hear people in the bathroom talking about you.

[Jon Stewart]

Right.

[Bill Simmons]

Are you just gonna stay there and be like, oh, cool, I hope all five of these people just rip me apart for the next 10 minutes. I'll just stay here. Or do you just kind of be like, all right, that's kind of fucked up.

[Jon Stewart]

Were there. I remember when I was just leaving the show is when, like, the Internet was kind of coming to bear.

[Bill Simmons]

Like, well, we talked about that. Because I remember talking to you. Yep. The end of 2015, and you left. And it reminded me of my dad retired from being a superintendent in 2009. And one of the reasons was because the phones were coming and social media was coming. And he's like, I gotta get out. I don't know where this is going, and I don't want to be in charge when this heads to where I think it's going. And that was kind of your mentality when you left the Daily show originally. You were like, I see where this is going and I don't like it.

[Jon Stewart]

Right. It stole, I think, a lot of the joy of it to some extent, but also the relentlessness of the news cycle and the redundancy of the news cycle. I sort of got to a point where I didn't know how to creatively elevate the show anymore. I just didn't feel like I had the ability to do that. And I felt myself checking out to the extent that it wasn't fair. You can't. You shouldn't. Just stay in a place because you can, because they'll let you, you know, you don't want to just coast. Combining that with. My kids were at that age where, like, I needed to be there. You know, they were 7, 8, 9 years old. Like, I needed to be there in a more explicit way than I had been able to throughout the run of the show. So all those things kind of coalesced into a very clear feeling of, you.

[Bill Simmons]

Kind of know when it's time.

[Jon Stewart]

Yeah, this is the right move. I've always said one of the best decisions I ever made was accepting the job. And one of the other best decisions I ever made was when I left. Because I'll never. I will. I would never have been able to get those years back. Just even though, like, driving them home from school every day and you just hear shit you wouldn't hear. I was there at the crying times before. Crying because I didn't want to go to school and crying because they didn't want to go to bed. Those were the only two times I got to see anybody. So having that experience broaden out, like priceless, you know.

[Bill Simmons]

But then you come back and now you're in a weird.

[Jon Stewart]

Now I went to. They go to college and I'm like.

[Bill Simmons]

Well, that's the other thing. You find out, oh, my kid's 15 now. He barely wants to hang out with me.

[Jon Stewart]

Exactly.

[Bill Simmons]

Yeah. All right. I guess. I guess I'm just an ATM machine now. And then occasionally we have dinner.

[Jon Stewart]

That's so fun. I was saying that to Paul Ruddy was on the show. I was like, you know, I think I made a mistake. Mistake When I was a little younger and that I didn't make any friends. And so when my son and my daughter went off to college, I was like, huh. Hey, honey, you wanna. You wanna watch a game and eat a sandwich? No.

[Bill Simmons]

New John Ham show on Apple. Jump in a couple episodes.

[Jon Stewart]

Yeah, yeah.

[Bill Simmons]

But you're in a spot now where I feel like you could do Monday and Thursday and probably. But.

[Jon Stewart]

But don't add Monday until, you know, the company is bought out by people that don't want anything to do with the Daily Show. And then who the fuck knows what's going to happen? I mean, look what they're doing now. That's 60 Minutes and CBS News and everything else.

[Bill Simmons]

I was going to ask you about that. This. It feels like we're in. We're in an area now that we've never been in in my lifetime.

[Jon Stewart]

Oh, it's insane.

[Bill Simmons]

People are 60 minute thing that was in, that was like the NFL and five other things in my life that I just felt like would go on for the entire time until I die. And now I wonder if it's going to exist.

[Jon Stewart]

Wonder if it's going to exist. Because an interview, they, they aired an edited interview, which is how all interviews air now. You can make comments about, well, I think I didn't like the way they edited it in the way that oftentimes people don't like the way they edited it. But it certainly doesn't rise to the level of libel, slander, or whatever the fuck else they think they're doing with a 2 billion dollar lawsuit. It's a purely subjective editorial decision that are made every day, including on Fox News and OAN or whatever it is that Trump feels like. But what you're seeing now is all must pay tribute to the king. And the price of that, the price of peace is different. You know, ABC had to pay 15 million. Bezos had to pay 40 million for a documentary on Melania. Zuckerberg had to pay. They just pay Trip. They just put money into the pot so that hopefully they don't get. They're paying like, what does that remind you of, Michael? Protection money, Right? It's protection money. So ultimately, at the end of this, does Trump burn our fucking country down for insurance money? Like, where are we headed? But the reason why the guy from 60 Minutes and the reason why the head of CBS News left is it's not even about the money, which I think is they've said is upwards of like 50 million. Imagine paying $50 million for fucking nothing just to get somebody to approve a merger. A, it's bribery, but B, the reason they all left is part of the deal is they have to apologize. And in that moment, these people who have built careers on their excellence and their integrity had to look and go like, all right, well, I hope I've done well enough that I can weather this, but there's no fucking way that I'm going to apologize for doing my job the way it's supposed to be done just because this one guy is offended by it. And ultimately, what an awful precedent that these media companies have set. But, you know, now, now he'll go after Harvard and Comcast or whatever the hell else he does, because a policy of appeasement always leads to more conquest.

[Bill Simmons]

And there's been tragic, and there's been a bunch of soul searching on the other side for the last year. On what about the Democrat liberal side? On what did we do wrong? How did we get this? How do we fix this? Oh yeah, that's been. Which has honestly resembled sports. Oh, you think?

[Jon Stewart]

It's, it's like a. Did they fire the coach and then.

[Bill Simmons]

They'Re gonna bring somebody in where it's like we lost in the second round. What happened? What do we do now?

[Jon Stewart]

Right.

[Bill Simmons]

Is it our drafts is our best and the way that, that the liberals Democrat side has approached it, it's almost like we have to blow this up and start over and we, we have to rethink our. And I don't, I don't, I don't feel like it's a six month fix because a lot of the same issues are on that side with, you know, authenticity, honesty. The same kind of media machine set.

[Jon Stewart]

The stage for it. The corruption of the system sets the stage for these kinds of disruptions.

[Bill Simmons]

Yes.

[Jon Stewart]

Like the, I'm convinced that the Iraq war and the way it was prosecuted and the fact that Bush and the Republican, you know that the establishment Republicans that led that charge, that is what opened the opportunity in the door for Donald Trump to demolish and take over the husk of that party. They had so destroyed their credibility that for somebody to come in with a new idea, take a hold of that apparatus and turn it on its head was exactly that. That was, that was set. The ground was set because of the actions of, in Iraq and all those other things. This and what happened with Biden and everything else will set the stage for similar opportunity in the Democratic Party. Whether or not someone is able to grab that apparatus and build something powerful and effective out of it will be the real trick. And we might not even know who that would be. But certainly the opportunity right now is there because the status quo right of that party is tainted. Everybody's got it on them, almost everybody. Which means that it really opens the door for somebody to walk in and go, I'll take your infrastructure, but the rest of you motherfuckers have to go or you have to get in line. And this is the new way that we pursue the vision for whatever the Democratic Party is going to be.

[Bill Simmons]

Or you need one or two great people, which is another like.

[Jon Stewart]

Or one or two not so great people who just, I mean, I wouldn't suggest that, you know, Trump is a great person, but he was a person with a vision. And when things are in disrepair, vision goes a long way. Vision and will. And I think it's entirely possible and I think it's actually the opportunity is there. I just hope that they seize it in the Right way. And don't just paper over, which is what you tend to think they're going to do.

[Bill Simmons]

We have two years here to figure it out. Not you, but just what. Just the country. It's funny, my friend Van Latham was over last night who works for the Ringer, and we were hanging out in the kitchen, actually watching the Knicks game. And he was asking my son about what are you studying in history? And he was Talking about the 50s and 60s and some of the things he's learning. We were talking about the 60s. This is one of those weird kitchen conversations when we're talking about all the great people in the 60s and then how many of them were murdered. Or in the case of Muhammad Ali, they wouldn't let him box for five years. And all the ways it got fucked up. But we just had this unusual collection of awesome, interesting one of one people all at the same time for whatever reason.

[Jon Stewart]

That's right.

[Bill Simmons]

And I wonder, can that happen again in the 2000s or in the 2000s? Is that even possible anymore? Where we would just have this, this confluence of. Of oh shit, hey. We have this person and this person and this person. Maybe we're in good hands again.

[Jon Stewart]

I mean, I think circumstance dictates the people that, that rise to those challenges. And I absolutely think, you know, opportunity almost never goes wasted. Like I think. I think someone always steps up and steps in. Maybe not to the extent that we'd want it to or maybe on the other side, but I always remain optimistic because there's too many. Look, I do too, on an individual basis. There's just too many fucking good people.

[Bill Simmons]

Yeah.

[Jon Stewart]

And I don't think these things all go in sort of cycles and those cycles change. And as they say, the arc of the moral universe is long, but it bends towards justice. But what people don't say a whole lot is. But it doesn't bend by itself. And there's a whole bunch of people trying to bend it the other way. So those things are, are necessary. But I think you also have kind of. You have to have kind of a more clear eyed view of what it takes to bend that thing and where you want to bend it. And there were. How old is your son now?

[Bill Simmons]

My son's a high school junior.

[Jon Stewart]

Can I ask you a question? And this is a personal question, I hope, and I don't want you to be upset with me. Does he forgive me?

[Bill Simmons]

Oh, for the wrestling?

[Jon Stewart]

Yeah.

[Bill Simmons]

When you ruin the wrestling event.

[Jon Stewart]

That.

[Bill Simmons]

You were the big surprise. I sent you the video. My son was like who the hell is Jon Stewart?

[Jon Stewart]

His son is like 7 years old. He's cursing me out. Yeah, the kid. The kid was cursing me out. Who. What is this asshole? Who is this?

[Bill Simmons]

You were the big swerve in a. Like a pay per view.

[Jon Stewart]

Yeah.

[Bill Simmons]

And my son thought it was going.

[Jon Stewart]

To be somebody else in SummerSlam. And it was a match between Rollins and Cena.

[Bill Simmons]

Yeah.

[Jon Stewart]

Cena was going to win his record championship and I was the swerve. I jumped in.

[Bill Simmons]

But we should. We should explain. You were in the exact same position I was in with my son. We're at that stage where you just want to impress your son. Your son loved wrestling and you're like, this is the most.

[Jon Stewart]

Couple years older than your kid.

[Bill Simmons]

Yeah, but this is you taking a giant bump. But I jumped out of the story.

[Jon Stewart]

Boy, did I take a giant bump on that. That was. That might have been the dumbest move I think I've made. And I was not. When I took the bump, I was not a young man. I think I was probably like 53, 4 or 5. Like, I was an old man taking an attitude adjustment from John Cena, which was stupid.

[Bill Simmons]

We blame Baby Doll, me and Jimmy Sal. Can I tell you something with that one? We were like, you left them. This is the most unprotected you've ever left a client. He just got. Here's the thing where James attitude adjustment.

[Jon Stewart]

Always has a problem. I do freelance, I do go rogue and I do shit. And then he'll just hear about it and he'll be like, what are you doing? And I'll be like, oh, it's just a. I got into a feud with this wrestler, Seth Rollins. You know, Nate loves wrestling, so we've been going to the wrestling matches and all that. Don't worry, it'll be fun. Oh, yeah, no, they want me to do SummerSlam. He's like, what? I was like, yeah, no, it's this thing. I'll go. It'll be fine. And so at SummerSlam. Well, it's actually on Raw where I took the bump. SummerSlam is where I ruined the match for Bill Simmons. Child, who I didn't think would forgive.

[Bill Simmons]

Me, but no, he's. I think he's forgiven you.

[Jon Stewart]

The bump.

[Bill Simmons]

I can't forgive the bump because that was crazy. Even if you were like 35, that would have been a crazy bump. That's a bump like past your 20s. I'm not taking. Making it.

[Jon Stewart]

Part of it is I don't think ahead. So I don't really, like, quite understand.

[Bill Simmons]

Practice it with you, though. Prac practice, they didn't take you in the back and do like.

[Jon Stewart]

No.

[Bill Simmons]

Put you on the big. Nothing comes in.

[Jon Stewart]

I think here's what he said. Just tuck your. Tuck your chin, tuck your head, yellow your chin, and I'll do the rest. And I was like, okay. And then chin. Yeah. So you gotta okay this so that I guess your head's not out. So you really. I think it's to protect you from. Like, really? Because I don't know if, you know, the floor of the wrestling ring is not soft. Yeah, it's. It's hard. It's on springs, but it's hard. It still hurts like a motherfucker. Yeah. So when we did it. Now, to be fair, WWE was very thorough in their medical examination prior to me taking the bump. Okay. About five minutes before I was supposed to go out there, a guy walks in, he goes, I'm the doctor. I go, okay. And he goes, how you feel? And I go, I'm okay. And he goes, okay.

[Bill Simmons]

That was it.

[Jon Stewart]

Any problems? You ever have a heart attack? No. Okay.

[Bill Simmons]

Yeah. Any major back issues? You ever been or not?

[Jon Stewart]

Right. Oh, are you old and decrepit and made of hollow? Are you. Do you have the bones of a sparrow here? Let's get you out there right now. So I went out there and I'm up on Cena, who's gigantic and muscular, and he. And there was. There's no. Like, oh, let me drop you down. With the attitude adjustment. It was the full. I hit, and the electricity went from directly from the back of my head down into my coccyx and through my legs. Like it felt like an electrocution, like you had plugged me into an outlet socket.

[Bill Simmons]

It's probably like. Like getting rear ended in a car. It's the same kind of sensation, the whole thing.

[Jon Stewart]

And they're like. Just play it like you're hurt. And I'm like, I can do that.

[Bill Simmons]

Yeah.

[Jon Stewart]

Because I'm hurt.

[Bill Simmons]

Yeah.

[Jon Stewart]

But the one thing I really learned through the experiences, if you're going to do something like that, tuck your shirt in. Because when you go down on an attitude adjustment on live television and you got that big old white tuna belly just popping.

[Bill Simmons]

I forgot about that. The belly popped out.

[Jon Stewart]

Little tuna belly popping out of the jeans. That's not a WWE Superstar look. That's not.

[Bill Simmons]

I'm glad you survived it. All right?

[Jon Stewart]

Thank you.

[Bill Simmons]

I took too much of your time. We got to end with the Knicks, though.

[Jon Stewart]

All right.

[Bill Simmons]

Are you going to game two?

[Jon Stewart]

So I can't I've got. It's a holiday week. I've got some I got to do, but I'm hoping to get there next week. Yeah. And look, man, I've loved watching this team. I really do. There. It's the most talented Nick team that I've seen them have in a really long time, maybe since I've been really paying attention, except in the 70s. And what I also like about them is they're good dudes. Like, yeah, they're just easy to root for. They're hard working. There's not a lot of, like, look at me shit. Like, they're really. They're a fun, incredible group. This has been a ride that, like, you dream about a little bit. It'd be great to get to the finals, but, man, Indiana's wagon like, it. They're gonna. It's gonna be hard, but, you know, they're not out of it. I don't. I don't view it like I viewed the Celtics series. I view it like we could be in every game, but then, you know, look, what was it? 138, 135. And before overtime even, it's like we're playing the Pacer style right now, and I don't know if we can survive that. Yeah, I don't know if we can survive that.

[Bill Simmons]

What do you think 1993 Mike and the Mad Dog would have said about that loss last night?

[Jon Stewart]

And Mike, that's what they do. They were gonna, like, waste the time.

[Bill Simmons]

These guys are.

[Jon Stewart]

Oh, yeah. Dog, dog, dog.

[Bill Simmons]

That is the most humongous loss the.

[Jon Stewart]

Knicks have ever had, dog. They're never gonna. You're never gonna see a loss like that again. In the Garden. In the Garden. I've been going to the garden since 1908. I saw. I saw Tunny fight Dempsey. I saw Tunny fight Dempsey in the garden. 19. And that was the only time I ever thought. Same, same kind of thing. Dogs. You.

[Bill Simmons]

You must have listened to that back in the day all the time, right? Mike and the Dog.

[Jon Stewart]

Yeah.

[Bill Simmons]

Was anything better than when they did the Oscars?

[Jon Stewart]

Nothing.

[Bill Simmons]

Mike and the Dog ever. That was. To me, that's. That created podcasting. Mike and the Mad Dog decided they were going to weigh in. I feel like they created it when they weighed in on, like, the 94 Oscars or the Emmys, I was like, this is just the motto for something down the road.

[Jon Stewart]

It is stunning how influential they were and are and are through broadcasting. More dog now, I think Francesco.

[Bill Simmons]

But I just feel like a lot of the people that have huge platforms now. And I include myself, were like, massively influenced by that specific show because of the interplay back and forth with those guys.

[Jon Stewart]

Yes.

[Bill Simmons]

Is really what podcast became the first taken.

[Jon Stewart]

All those other ones, I think, are in many ways direct shows. Yeah, yeah, absolutely. Those guys were. And when they came on the air, the Fan was nascent. Like, it wasn't as big a deal yet. Stevie Summers, you know, at night doing all his stuff and Dog and Francesca and like, it lit up sports in a way that, you know, for New Yorkers was like this, you know, and now everybody does kind of their impression of that. But. But it's amazing. And to see especially Dog, like, still going strong, it's kind of great.

[Bill Simmons]

No, he's.

[Jon Stewart]

It's a long career and with.

[Bill Simmons]

With some chapters to it, too. Well, now the fan used to listen to the fan.

[Jon Stewart]

It.

[Bill Simmons]

It seems like some of it is a little performative because the clips are really funny.

[Jon Stewart]

Yeah. Well, it also has to be, you.

[Bill Simmons]

Know, there's two bald guys just, like, absolutely losing their mind over the protection behind Aaron Judge or what that Juan Soto seems unhappy.

[Jon Stewart]

Yeah. The problem I have now sometimes with the Fan is a lot of the voices sound the same. Like, the nice thing about Dog and Francesa is. Yeah, they were like hall and oats. Like one guy saying high blues and the other guy and every now and again. So that treble and bass really worked. Now you get shows that are like, treble trouble and it's. You don't know who's talking. And they're all at the same pitch, and it's just kind of cacophony and like, you say, pretty performative. Pretty obviously takes with, like, kind of holes in them. Still fun to listen to, but, you know, but we're also old heads. We're old heads.

[Bill Simmons]

New York radio will never die. The. The. The one thing with. I'm blanking on the. What's the guy's name? Dog was on when he goes on first take and he does basically national version of the Dog. That was the part I never thought he would be able to navigate the way he has. I always felt like. I always felt like it was. That was a New York show with New York people. And I never thought. I never thought he would become a national treasure. Cause I think he's great.

[Jon Stewart]

He's so legitimately funny that I think that translates through it and the way that he just runs through, you know, the whole.

[Bill Simmons]

Enjoy his sports and I got.

[Jon Stewart]

Take a gummy. I'm going to take a gummy. I'm going to sit down, I'm going to take a gummy and watch it. I'm going to watch the Yankees. You know, he just, he, he legitimately is just an entertaining personality.

[Bill Simmons]

One of the things I learned from that show was how completely seriously they took everything. Like, they would talk about tennis, right. And dog would have these passionate opinions about, like, Monica Seles, right, Mike? I, I think she might be the best woman's player ever, like, right now. And it just, it just would go all in and be like, wow, this is an incredible, incredible takes.

[Jon Stewart]

But the nice part about them is they were a hot take in a sea of, like, lukewarm water. So it's so, so brutal. Yeah, it was so stood out for just, it's, as we said earlier, like, there was an authenticity to it, these two guys, and, and just, it was brilliant.

[Bill Simmons]

PGI was another one like that. I feel like those were, if you're talking about podcasting, is a great one. The form, those two, the, the interplay and the chemistry is.

[Jon Stewart]

I've always loved it. Corner. You know, those guys, you know, and again, like, sometimes duos really are more than the sum of their parts. Like, those guys are great on their own, but like dog and friends, as it were, together, it was just, it was magic.

[Bill Simmons]

You know, it was like that. Larry David and Doc Rivers would have a great talk show. I'm telling you, they have it. The combo of those guys, it's like a fast.

[Jon Stewart]

Larry David is doing dog. He's doing dog.

[Bill Simmons]

Yeah, he was there last night.

[Jon Stewart]

She's the greatest at all time. She's the best.

[Bill Simmons]

What is Townes doing?

[Jon Stewart]

What is he doing? Towns, drive the lane. You're bigger than he is. By the way, when Towns was posting up on jrue Holiday. What? Why would the Celtics put Jrue Holiday on Townes?

[Bill Simmons]

I think people try to Jedi mind trick Towns with smaller people, hoping he'll elbow them in the face or bowl them over.

[Jon Stewart]

Yeah, that's why it's just like, what's going on here because every now and again, like, you'll see a bad switch and, like, somebody will end up on towns who's like 6:3. Yeah, but this really, like, it happened enough where, like, oh, no, that's the plan.

[Bill Simmons]

People try to use Towns against himself, is the plan. Ah, the good and bad of Towns. They hope the bad goes out. Wait, last question. Are you worried about Juan Soto or. No, he played, they played the Red Sox this week and he seemed, I, I, he seemed a little sullen. I would sullen is the word I would use.

[Jon Stewart]

You don't remember the first year of Francisco Lindor. You don't remember the first year of Carlos Beltran. You don't remember. And by the way, you don't remember the first four years of Jason Bay. Like, people come in there. First of all, Juan Soto right now is not failing. He's not all star Juan Soto, but he's still a very solid performer in a lineup that's underperformed recently.

[Bill Simmons]

But you're not talking about the emotions.

[Jon Stewart]

He's played a much better outfield than I think people thought he was going to play. And I'm not going to read the, like, facial expressions of a superstar that's going to be here for 15 years.

[Bill Simmons]

Who already seems sad.

[Jon Stewart]

Yeah, like, I didn't. I never thought of him as, like, the happy warrior to begin with. Like, I didn't bring him over here because I, you know, get excited about it because I thought he was super entertaining and gregarious.

[Bill Simmons]

I just thought, see, this is what Mets Nation needed. They needed this defense.

[Jon Stewart]

But we're always worried about everything. Again, you're talking about a fan base that, like, whatever will go wrong. Whatever could go wrong goes wrong. Tyrese Halliburton throws up a fucking prayer. It hits the back of the rim, goes straight up in the air. And in any other universe other than the New York Knicks universe, it goes over the backboard, right? That's the arc the ball is supposed to travel.

[Bill Simmons]

It doesn't the highest, other than maybe the Kawhi shot, the highest. I think a game winner has gone or a game tire.

[Jon Stewart]

I've never seen anything like it. For God's sakes. The. The little stat track said the Knicks at 99.8%, they're going to, like, only in New York, New York Mets are going to go to the thing. Un sespius breaks his ankle riding a bull. Like, only shit that can happen happens to us, and over time, you expect it. So, you know, that's what they've done with the Mets is already fighting the gravity of our history. What Cohen has been able to do with them, what Stearns has been able to do with them, is to counteract the gravity of our history in a way that looks like we might actually be competitive for years. That's never been the case that happened.

[Bill Simmons]

With the Red Sox when, when they, they. Specifically, when they got Manny 2000, they actually spent money on him. And it took a couple years, but at least, like, the foundation was laid for, like, oh, we traded for Pedro. We Got Manny right now we can actually like maybe fight the Yankees.

[Jon Stewart]

You also built a farm system that started to bring up studs. Yeah, like that's the key. Like the Mets, even before when Cohen was there, they were still doing shit. Like all right, well we want to be good. Who are the oldest pitchers we can pay. Find me two of the oldest pitchers and pay them more than anybody's ever gotten and maybe they'll, you know, make us good. For six months now they've taken. Stearns has come in and completely flipped the approach. He's building a ground up solid infrastructure. Will you win the World Series? Who fucking knows? The World Series is. It's a crapshoot. And the Dodgers are going to be there for a while and the Yankees are going to be there and. But they're at least you want sustainably good. Thank you.

[Bill Simmons]

That's what, that's what the.

[Jon Stewart]

And that's what Leon Rose and Thibodeau have done for the Knicks. It's much harder to keep going in the NBA. But yeah, you know, because I, I don't know how you feel about this, but I feel like the NBA cap rules and all that other shit it up.

[Bill Simmons]

It's we've been talking about on my pod constantly. They fucked it up.

[Jon Stewart]

We not able to pay Hartenstein what we wanted to pay him. That makes no sense. We wanted to keep that dude.

[Bill Simmons]

I know.

[Jon Stewart]

And we couldn't.

[Bill Simmons]

The problem is they reward bad teams who throw away seasons and get high picks is a better strategy than just like signing players smartly, making good trades, drafting well and then you somehow get penalized for it. They, they shouldn't have been penalized for the Hartenstein thing. Cause that was such a great, such a great signing. But then they had.

[Jon Stewart]

If they had been able to keep him. My guess is they probably.

[Bill Simmons]

They don't do the towns.

[Jon Stewart]

Yeah, they would have run it back. Still would have gotten bridges and then you would be a deeper team. Yes. I loved how when they were deeper. I like that like Indiana's built really well. They really are. And this is interesting too. I wonder what you think about this. This is such a repudiation of like the super team. Like these are great teams but these aren't superstar teams.

[Bill Simmons]

Right.

[Jon Stewart]

Other than like OKC's got.

[Bill Simmons]

You know why? Because the league is so much deeper now. You can actually build a team a little differently. You don't have to have like the top heavy best two guys. You can actually go seven, eight, nine deep. That's what the Celtics tried to do. And then they had too many injuries this year, but.

[Jon Stewart]

Right. But even the Celtic. Imagine having Tatum and Brown and then like having to worry about holding your team together like teams shouldn't have to worry about holding together like that. That's bullshit.

[Bill Simmons]

You're preaching in the choir. Jon Stewart, this was great. Thank you for all the time. I'm glad we finally did this on a podcast. It's always good to see you.

[Jon Stewart]

Yeah. Good seeing you as well.

[Bill Simmons]

All right. I appreciate it. Thank you.

[Jon Stewart]

Bye bye. Go next.

[Bill Simmons]

All right, that's it for the podcast. Thanks to Jon Stewart. I had a great time thanks to Gahal and Eduardo as well. Don't forget you can watch all of the clips and videos from this podcast on the Bill Simmons YouTube channel. You can watch the rewatchables on The Ringer Movies YouTube channel. You can watch everything we're doing as video podcasts. And Heaven Can Wait is going to be the next rewatchables on Monday night. I am also on the Prestige TV podcast this week talking about your Friends and Neighbors season eight. That's your Friends and Neighbors episode eight. Hopefully it gets to eight seasons. But the eighth episode, I think we're hitting the end. Me, Joanna Robinson and Rob Mahoney. So if you watch that show, go check out the podcast that is going to be going up on Friday. Enjoy the three day weekend. I'm going to be back Sunday afternoon with Rosillo and I will see you then. Must be 21 plus in President select states for Kansas in affiliation with Kansas Star Casino or 18 + in President D.C. gambling problem. Call 100 Gambler or visit rg-help.com call 1-887-89-7777 or visit ccpg.org chat in Connecticut or visit mdgamblinghelp.org in Maryland. Hope is here. Visit gamblinghelplianma.org or call 800-327-5550 for 24. 7 support in Massachusetts or call 1-877-8-HOPE NY or text hopeny in New York.