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Host
You're listening to DraftKings Network. Welcome to South Beach Sessions. I'm excited about this one. It doesn't mean I haven't been excited about the others, but my level of admiration for this person with what he's done, just sort of flippantly being a journalist while also being a comedian, honoring the things that his father was about in what now passes for the old south, when he was a journalist who was more joyless than he was. And so I sort of recognize in. In you some of the things I saw at my dinner table where my dad was really unhappy at work, and I'm like, I don't want to do it that way. Like, I. I'd like to, but there's got to be joy in it because I don't want to be miserable. But Roy Wood, Jr. Should be, if you've been paying attention, the Daily show host. Now, thank you for that. If television executives weren't perpetually idiots, he would already be the Daily show host. Because you're what you've done. I admire you so much, but at least in part because I don't think many people know how hard it was for you to make a career out of all of this.
Roy Wood Jr.
What's weird, man, is. All right, here's like, because I started comedy at 19, which I would argue if you start anything as a teenager, you're just learning the art of it. You don't have an opinion. You don't have an angle on what you want to do. And then when you start realizing, oh, no, these are the things I really want to talk about that I really care about, well, then that comes at a cost to a degree, because now certain clubs aren't going to book you or you're going to deal with certain criticisms. So that part of it has always been a weird balancing act. But at the end of the day, if I'm not excited to talk about the stuff I want to talk about, then I can't. I can't be up here.
Host
But foundationally, when did you decide that you were going to do funny as a living?
Roy Wood Jr.
I don't. I don't know. Like, that's a weird. It's a weird question to answer because I just kind of got. I fucked myself, for lack of a better phrasing. So when I was in college, and we can go down this rabbit hole if you want, but, like, when I was in college, When I was 18, 19, I got arrested for stealing credit cards to buy clothes. So we're buying jeans and shit and selling them on campus. Whatever. I get caught, I think I'm going to prison. That is what my lawyer told me. That is what everyone. Well, these cases are usually adjudicated at a five year sentence, but with good behavior. You're a young man with no priors and.
Host
But it's a federal felony, right?
Roy Wood Jr.
Correct, Correct. So I end up somehow getting probation instead of prison. So in that time, up until sentencing, I started doing stand up comedy just because I had no friends. I was sad. I guess you could. I stopped short of saying depression, knowing now what people who are depressed deal with. But whatever it was, I was in a bad place. Comedy made me happy. So when I found out I got probation, I just kept doing comedy. So when I got back in college, at that point, I was so focused on stand up that I made good grades just so my parents, just so my mom couldn't say shit to me. Like, you can't. You can't tell me I'm throwing my life away with comedy. I'm over here on the dean's list. So when I graduated with my degree in broadcast, no one would hire me because I had no internships, because I spent every summer doing comedy. But then when you do the math and I look back on it, I go, oh, that was my internship. It was comedy. And so when I graduated from school, I had two jobs that I could have applied for and probably would have gotten. One was the Tampa Tribune to do the page two sports 2:00am oh, you.
Host
Could have been a sports writer. You were headed down the possible sports writer.
Roy Wood Jr.
I was on that. Stuart Scott, Kenny Main, Van Earl Wright, Jenny Moose type, offbeat. Those were the journalists that I respected growing up.
Host
You worked at ESPN some. And you were watching Stuart Scott Baker basically change what sports television looked like. Because Stewart Stuart Scott was rebellious. I mean, all he was doing was being black and blessed.
Roy Wood Jr.
But I didn't know that. All I knew was just that this talk. Like me, but he's cool, but he's doing. He's talking about what I love, but he sounds like me. He was the first person. Because before that, before Stu Scott, it was Fred Hickman. And Fred Hickman was the more buttoned down, more appropriate, more like my father journalistically. And Stuart Scott to me was the evolution.
Host
That's so funny. Hickman was 80s black man on television. Badass, but serial. Yes. Like, this is a man you can trust. Just look at it correct.
Roy Wood Jr.
Like, because he's from the Ed Bradley. Ed Bradley was probably Fred Hickman's OG Journalistically. So.
Host
Oh, so you're watching Stuart Scott changing. Like he's allowed to be in the playground of sports. He doesn't have to be serious journalist.
Roy Wood Jr.
Correct. As was Van Earl Wright, who had seen in headline sports at the time, people talk real crazy and talking to the highlights real fast. And the Jays beat the A's and the bull still went from the Hornet. I just liked it. I like. It was different. It wasn't the traditional box of conservative behavior that I was told that you have to adhere to. So, yeah, so I get a job offer. I had a. I had a job opportunity at the Tampa Tribune. I had one at the Birmingham News. Both were going to pay about 17, 14 or $17,000 by my calculations that year. At this point, I'm going into my third year of comedy. By my calculations, I would have made 27k that year. Then I stopped minus gas and all of the other stuff. But I worked hard enough in those two years in school that by the time I came out, I just did the math and it just fiscally made more sense to keep doing comedy. And every year, business decision. And every year since. Since then, it has fiscally made more sense to keep doing comedy.
Host
But this is the part that I don't think people can possibly understand of what it is to do that. To be someone who decides to make his career with the bravery of I've got the expectation of funny and all I have is my talent, my humor, my jokes, my charisma. I'm going to make a career of this with no health insurance. I'm going to do sad comedy clubs and I'm going to learn how to make 19 people from Mobile, Alabama laugh. Because on you, guns pulled on you.
Roy Wood Jr.
Paid in cocaine one time. There's. It's definitely been called the N word a couple times from heckler. It's like that. But you have to remember, when I started, I didn't have anything. I was supposed to be in prison. So this is better than prison. So this idea of taking your risk and a jump, it wasn't. That just didn't register. And God bless me, because I just was too dumb to know how wild of a decision I was making. I had two roommates, bro. All I had to cover every month living in Tallahassee was $375. And I did that at Golden Corral. So the money I was making on the weekend, that was just extra gravy. And I was riding the Greyhound.
Host
I want to hear about the Golden Corral gig. I mean, how bad were the earliest? The earliest gigs? This wasn't that long ago. It's 20 years.
Roy Wood Jr.
The. In that. In that 99, 2000 era, Southern Buffet. No, Jordan Corral was.
Host
Bro, I'm not. I'm. I like Golden Corral as a restaurant. Look at me. I'm saying playing it as a venue.
Roy Wood Jr.
No, no, no, no. I worked there. I worked. I worked 15 hours a week ago.
Host
Okay, all right. I misunderstood you. I thought you were playing Golden Corral, that you were doing something up there.
Roy Wood Jr.
Oh, God, no. That would be miserable. Monday through Thursday, Golden Corral. Thursday night, I take the Greyhound to wherever my weekend are. Monday morning, I'm back in Tallahassee to take a night class, then go back to Golden Corral. And that was the wash, rinse, repeat while I was in school. And so then after about a year of that, my mom got me a car. Well, she put down on a car for me. And that opened up essentially the whole Eastern seaboard to me every weekend. And, you know, that's why, you know, I say it a million times. My mom is my biggest supporter because even when she didn't understand why I was doing comedy, she just want me to do it safely. So here's a car stop. Sleeping in the bus station, that's going to get you murdered. I'm like, you're probably right. I will now go sleep at a truck stop, but I would at least sleep at a Flying J. And it takes years of traveling to notice this. But flying Js are the only truck stops that I've seen by design, by corporate design, where the cash register is closest to the parking lot. It's not in the center of the store. So if I'm going to get robbed or murdered, there will be a witness, at least one person.
Host
That's how you were touring. That's how your career began. I'm going to see if I can do this safely. Up and down the Eastern seaboard with jokes.
Roy Wood Jr.
Cheaply, not safely. What is the cheapest way to do this? And more often than not, it was. It was sleeping in my car at truck stops. If you got lucky, you could meet a girl off of a dating site and maybe if the date went well, you could sleep on the couch. Like, it wasn't even about sex. It was just, I need somewhere to stay tonight. You know, it show is late. Like, if you're. If you. If you're a good enough date, then maybe they'll offer, you gotta get back on the road. It's late. Just stay on my couch. Thank you.
Host
You're just. This is how you're making a Career of it. People couldn't fathom it now, right? Watching you on television, they couldn't fathom the idea that you were and thrilled to do it. Probably.
Roy Wood Jr.
It was amaz amazing. And I couldn't, like. I don't. That's why I could never tell anyone that. Like, anyone in their, like, late 20s, early 30s, where they go, well, how do I do it? You know, the way you do. Like, you can't. I think that's one of the biggest fallacies in any career is thinking that you can do it the same way the people you look up to did it. The game has changed. Gas was also a dollar 29 cent a gallon when I started. The money in standup is exactly the same. 50 to 75 to open, 100 to middle. You might get 200 to be the last guy on stage, if you want to call that a headliner. But gas is triple. Hotels are more. The gigs are far and fewer in between. So there's. And. And then when I got to Birmingham, I started interning at a radio station there that ended up at. For like 12 years. If the gig was less than four hours, bro, I drove back that night because I need to be on air in the morning. I'm trying to. Trying to be Stuart Scott. So I can't not, you know, I can't not water this plant. So you find yourself just kind of living on both sides of the tracks at all times. But when you're young and you're just driven and you're fueled by that, it's. It's beautiful. And then one day you're 44, and both of your industries that you're in are on strike. Your show is in flux without a host, and the economics of touring have changed immensely. And you still have to get back out there with that same fever, that same, you know, passion. And that's a very difficult thing to recreate when you have a child and you have responsibilities. And I think that part of it, you know, it's like Rocky III after Clubber Lane beat the shit out of Rocky. And then Mickey sits Rocky down like, yo, man, you got rich. You got comfortable, you lost the fight.
Host
It happens that fast. It's hard for me to fathom that the industries could be that fragile, that someone with your talent, your name, your brand would see not just corporate change throughout America, but also comedy change in ways that would demand your evolution. That if you got. If you got fat and lazy with the idea, I don't have to hustle just as much as I was at those Truck stops. Because now I got a kid, too. Like, back then, it was just me. I could sleep in truck stops. I can't believe that career could be that flimsy with someone not just with your talent, but your bonafide.
Roy Wood Jr.
It could be, and you may be right, and we will see. But that does not make me comfortable because I, you know, like, when people talk about, like, the light at the end of the tunnel, right, where people go, oh, there's a light, and keep running, and one day you will achieve the light. To me, the light in the tunnel is the train coming to run me over. So I've always operated from a career standpoint. I've always operated from a place of paranoia, of this being a finite journey. I hope I'm wrong, but I'm not going to bet by just sitting still and just going, oh, no, everything will be straight. No, bro. I put dates on the books in February before the. When I heard a rumor that there was going to be a writer's strike. Call my people 30 cities. Let's go. Let's find 30 cities. And now that's up to, like, 40 cities, I think we're going to do now.
Host
But this is. This is one of the. This is one of the reasons that I admire your journey and just how hard all of this stuff is to make an entire economy around. I'm just going to pop up in 40 cities. It's me and a microphone and you. And I'm doing another show. I'm doing other things, but of course, I've got an act that's ready, and it's going to be fresh, and it's not. And I'm going to work. I'm going to work the America to see if it morphs into what, a Netflix show? Because that's what's buying that, correct?
Roy Wood Jr.
You do the things that you are passionate about, and then people will find a place for you to do them within their organizations. And I think that's the biggest thing that has happened to me. That's the biggest transition in the industry, like entertainment. Like, I mean, really, if you want to get into sports, right, Like, y' all was talking about McAfee on your mothership show a couple of weeks ago, right? When ESPN was having, you know, the bloody. The Bloody Sunday, right. We have transition from a place, in my opinion, within entertainment. I pay close attention to sports because sports as an industry, television sports, the studio stuff, it operates at such razor thin budgets compared to other parts of the industry. If we're talking daytime talk shows, late night Talk shows, scripted shows, etc. Sports has always operated the most razor thin. So how sports goes to a degree can start informing me on how late night is going to go. That's just what I believe. I could be wrong, but that's just what I believe.
Host
And of course you have to study it that closely because your paths, you could have ended up on either one of the paths. You could have. You, you very easily could have. You would have been great as the funny sports writer on ESPN who then turned that into multiple shows. Because there is no funny sports writer at espn. Espn.
Roy Wood Jr.
You know what put me up on Game with that? I had a year. And this is also kind of why I'm in this mindset now, career wise. But I had a, I had what I, what I'll call a drought year in 2014, the year before I got the Daily Show. So I was blessed enough to where I had a buddy that I was in journalism school with and he knew some producers up at espn. And hey man, there's this lady, Jamel Hill and Mike, Mike Smith, they're doing this show called his and Hers. If you're ever near Bristol and I go, I'll drive. And at the time I still lived in la, but if I had a gig anywhere in the Tri State, hey man, can I come up and pick?
Host
Because you saw how rare it was for a 6pm sports center to give an opportunity.
Roy Wood Jr.
No, this is pre 6pm sports center. They were on at two in the afternoon two years prior to when they did the six.
Host
Oh, like numbers never lie. The show on ESPN era. So you're like, I will drive from Los Angeles, Angeles to Bristol to be on ESPN too. Because there's a space where someone gets funny on television.
Roy Wood Jr.
If I'm performing anywhere within five hours of Bristol, I'm adding a day and I'm driving. I'm gonna be in that studio.
Host
Because you're a hustler and because you see opportunities like, you know, you know, that's exposure.
Roy Wood Jr.
It's exposure. It's paying me nothing, but it's exposure. And then that got me access to Bomani, which got me access to Sports Nation, which got me access to West Coast ESPN. Pretty much anything in ESPN LA. That shot I did in 2014, I came in. And then the next year the six happened. And then 2015, I get the Daily Show. And part of it was on the strength of some of the segments that I had done on espn because the sports, sports and comedy is hard. It's, to me, it's harder than Politics and comedy, because at least the politicians, they don't take themselves seriously. They know they're running a hustle, and you call them out for it, and they just grin and go, yeah, what you gonna do? But if you call out an athlete or owner, a fan base, a city, they. They don't like that.
Host
It's funny, isn't it?
Roy Wood Jr.
They don't like that.
Host
But just how. How ridiculous that perspective is.
Roy Wood Jr.
And all you do is catch a ball, but you can't take the criticism. Meanwhile, my man over here making these crooked laws is getting all types of poor people done dirty. He can perfectly. He can take criticism just fine. And so, you know, ESPN is a network where you got to kind of. There's guardrails up within the jokes. There's not a lot of comedians that come on that network. Just in general. Let's just be real about that.
Host
So it's so strange to me. I don't even understand it.
Roy Wood Jr.
It's not strange. Comedians are like, you can't control us. We're professional dynamite jugglers. And everybody wants to see dynamite juggling, but they don't want the shit to go boom on their show. So they would just rather not book comedians.
Host
I had never thought. I booked a couple of comedians, and it was cumbersome to do, and I'd never given it a thought, honest to God, that there were guardrails there to make sure that you couldn't come on there and make such a noise that you got your credit, you got attention for you, but somehow soiled the Disney brand.
Roy Wood Jr.
Yeah. I mean, you can make jokes or two, but let's keep them within the lines. But it depends on the type of comedian you book. I mean, I generally don't do humor that crosses into that in general, but there are comics who do that, I think do a good job. I'd say the one who toes the line perfectly is Bill Burr. You know, Bill, like, still does. Like, they bring him in the booth for Red Sox games now and just let him just open mic, live tv, and it's perfectly on the line. But that's also a testament to Burr's professionalism, because he knows where the line is. He could cross it if he wanted. But, like, in that time. I'm sorry, I got on this tangent, but, like, in that time, that taught me a lot about just hustle in general and just busting your ass and just trying to always make sure that you have another opportunity. So I never have sat pretty and went, oh, everything's great. It's. Oh, I Did that really well. Okay, what's next?
Host
But how does this go for you? Because I can't imagine what it is to be you right now. And I don't know what they're doing as they look for a replacement hose. Trevor Noah does it very well. Almost an impossible spot, really. Jon Stewart did it so well to come after him. Trevor Noah does it successfully. The next slot for that seems perfectly set up for you.
Roy Wood Jr.
It's, it's. Whoever comes in after Trevor will never have it as bad as Trevor. It's the, you know, the. You don't want to be the guy that replaces the guy. You want to be the guy that replaces the guy, you know. Trevor also was far more unknown domestically. He was huge internationally, but he was far more, far less known, Less known domestically at the time. I don't envy what he had to do in replacing Jon Stewart, but I just think that when we talk about who the next host is, be it me, I know Hasa Minhaj's name is in the hat. There's a couple of the guest hosts that we've had. Some of the ladies, their names are in the hat. So regardless of who comes in, there's also a bigger question of what is late night after the strike and with the changing economics and blah, blah, blah, like that is a question that also has to be answered. To me, the bigger question is what is the show gonna be? Because if somebody goes, oh, you should host the Daily show, what I hear is you should host the pre Trevor version of the show, the pre Covid. Whatever of the show. I don't think fiscally most late night shows, any new iterations of late night shows, I don't think they're gonna look like that anymore because I just don't know if the networks are committed to putting that type of money into that type of, type of product anymore. And that's a question you can't answer because of the strike. So I can't call you and go, hey, are you really going to put some money in this? Okay, cool. Leave my name in the hat or take my name out of the hat. But in the meantime, I can't wait. Amen. Give me 50 cities. 40 ain't enough. The actors just went on strike. Look like they going, yeah, see if we can add Canada or some Australia. Yeah, cool. Click.
Host
People don't understand that the industry is trembling right now and you just had to book a 50 city tour because you've got to keep the economy of your brand alive as the industry shakes.
Roy Wood Jr.
And that's A blessing. And that is a blessing that I have from 25 years of grinding to be able to go into markets, into certain venues that know me and trust me and know that, you know, my fans will come out and see me. Every actor and writer doesn't have that. So it's my job to be out there and try and fight a little bit for what's right and make sure that I'm holding the line and not going and talking to the network behind everybody's back. Yeah. So can I host a length? I would love to have a Late Night Show. 1000%. I would love to have a late night show. I think my iteration of what I've done on Comedy Central at some point has to come to an end. I don't think just sitting as a correspondent into perpetuity benefits me. You know, in the long run. You know, it's kind of that. If we can go sports for a second. To me, it's that Cordell Stewart slash era where they didn't want to make him the starting quarterback. And they go, okay, you can, you can be in the slot every now.
Host
And then and before the revolution at the position.
Roy Wood Jr.
Correct, correct. Hey, you can quarterback third downs during blowouts and you can be in the slot when we then shotgun or something with Heinz Ward and whatever.
Host
But this is why I would have loved to have you on ESPN talking about this stuff because six time executive of the year Bill Polian thought LaMar Jackson, the MVP, wasn't a quarterback. Like, I would have loved for you to be able to slice, slice that up playing in sports instead of just visiting on occasion because it, because it spurs your curiosities.
Roy Wood Jr.
I like, I like that. I've always loved sports, man. I'm not good at it. I'm not good at it.
Host
But you'd be good talking about it if you spend 20 years carving up what you've carved up in entertainment and comedy, if you spent the last 20 years taking the path you were originally going to take of. Let me see if I can figure out how to be Stuart Scott. And I'd given you a microphone to be on one of these debate shows that you could have made your own.
Roy Wood Jr.
Yeah, yeah, I think I could have done that. I think I still could. And that's the beauty of where I am now creatively, is that you kind of get your Tom Hanks at the end of Castaway where you just. There's all these different roads. Which one do you go down? And that's kind of what I've had fun during this Downtime of just creatively trying to explore. It's like, okay, well, if it's not hosting the Daily show, well, then what would you host? What would that show look like? Well, maybe you should go to Miami and sit on the beach for a couple days and relax and try to create that and go, oh, Lepatar's in town. I should go over to his studio, say hello. Which is essentially what's happening right now, you know, So I. I'm just not in a position, and I don't think I'll ever be comfortable in a position of waiting on an industry to decide when I get my next opportunity. And I think this is the first time in my career where I felt that. That real uncertainty for the first time. And my rent's not $375 anymore, so we gotta go out and do something. So the first thing you do is tour where you can, and then you start coming up with your ideas. You write your films and your movies and you can finagle a book deal and all of that stuff. But to me, that stuff is all hot and cold. I enjoy conversation. I enjoy. The thing that I loved most about live radio was talking to regular people. Just talking, just taking calls.
Host
I wanna talk to you about your career and your dad's career. But what you're artic. Articulating now. Freeing, scary. Both. Which is it? Of more freeing. Scary.
Roy Wood Jr.
It's scary and exciting because you don't know what the hell you're doing, but all you're doing is trusting your instincts. And what have you done your entire career? But trust your instincts. That's all I've ever done. I can't tell you why I did xyz. Going to ESPN for a year and just working repeated shows for free felt like the right thing to do. I go and I do Jamel and Mike. I do his and hers. They're OG podcast, which rolled into the 2pm show. I do that. I think I might have popped up on Bomani, had a situation at some point before high noon, and they would use Bomani and stuff. Then they would start using me at Sports Nation. And Sports Nation is where I really settled in every three weeks, just on there for one reason or another, doing something, talking about whatever current event was going on. And when you look at my job in that chair, it really wasn't any different from radio. Because in morning radio, as the comedian, as it was told to me by my. By my radio sensei, Samuel Mack, the job of the comedian is to offer the viewpoint that no one else in the room possesses. The three people in the room possess the views of the listener. Your job is to be Crazy Town and come up with the most alternative counter art. Whatever it is, it can't be something that any three of us have already said or you think we would say. Until you have that thing to say, your job is to sit here and be quiet and answer the phone. And I was so shut up until you have something funny to say. And that was the job. And so that was the habit of how my comedic writing started. And then that fit perfectly into espn because Beetle, Marcellus Wiley, and Max Kellerman, they were going to handle the structure, stats, nerd stuff. My job is to come in and say something silly.
Host
Roll grenades across the floor.
Roy Wood Jr.
That's it. That's your job. And then you get to the Daily show, and lo and behold, what's your job now? Roll grenades.
Host
But you're a journalist in the middle of all of that. You are honoring your father's work through comedy by doing legitimate journalism on a show. I can't believe this happened on my watch. And I was stunned to. But for Jon Stewart to so thoroughly. For that show to be so smart that it so thoroughly took over news anchors, so that Jon Stewart was the most trusted newsman in America by poll was because you guys were reaching people with creativity instead of the news, like Fred Hickman would deliver it. You guys were delivering to the people something that they were happy to be nourished because it was smart and funny, and it felt less like they were being lectured at.
Roy Wood Jr.
It was. But there's a pressure in that, because then comes the expectation of we must do the thing that you think we should do. That's the most righteous thing or cover the most righteous stories, and they're stories that we don't always get to or we're not able to tackle with the same degree of depth as other shows. And I think that's because we have to be funny first. Like, you know, like, watch Vice News and then tell me how many of those stories are on us or Oliver or Jon Stewart over on Apple. Like, it's not gonna be the same hit rate because we still have to be funny. Now, Oliver and Stewart shows, respectively, go to different depths on particular problems than we do Daily Show. We kind of have to hopscotch around. So certain stuff, if it's a super nuanced issue, it may not be the right story for Trevor to carry at the desk. It might have to go to a correspondent. And so that becomes a whole nother. Set of planning and production. But being on the show is definitely, it's far more journalistic than anything I've ever done. I'm definitely like, when I first got there, I was like, oh, shit, I have to use my degree. I have to think about what the story is, what we're trying to say, and then also what is the funny way, you know, to go about talking about this thing? Because not everybody's gonna like it. Not everybody's going to agree either. And that's the thing. That's when we talk about, like divisiveness and blind loyalty in politics. I think you're going to deal with that the same way you do in sports. And that's why I've always felt like sports and politics creatively kind of build from the same, you know, bag of Legos. Because it doesn't matter what you say, doesn't matter how centrist it is about a particular team or ownership, somebody's going to call you, call you out and say you're playing favorites.
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Host
Favorite thing to think hard.
Ad Read Male
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Host
Oh, easy. Yeah. Ice Cold milk.
Ad Read Male
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Roy Wood Jr.
Dude.
Ad Read Male
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Host
It seems crazy to me that you're saying that. And I don't think you're wrong either. It's just not something that I'd ever considered the idea that politicians or the political journalists would have it so much easier because they're all playing the same game and they understand it. Whereas sports journalists. The head coach doesn't interact with us the same way with a wink when he is criticized that sports would be more serious than politics.
Roy Wood Jr.
Seems crazy when. How often when a politician snaps back at a reporter, it is a huge story. I think Ron Desantis said something slick back to someone. This may have been a couple months ago, but he didn't like the question, so he was real snippy. And that was a story within the political news cycle for 36, 48 hours. Y' all get cussed at every day in the locker room. I don't like that question. Next question. Or the coach is all indignant about it, and then for the next four days, he won't call on you or your organization.
Host
Crazy.
Roy Wood Jr.
It's Funny, the next press conference, I'm not gonna talk to that news outlet because you said that our guy didn't have a good game. Shoot, he didn't. Whereas a politician would go, yeah, I didn't have a good game. But let me show you how that still benefits the American people. See, you have to understand when you're missing shots, what you're doing is creat opportunities for other people to rebound the ball. Like that's politicians. It bounces off of them. But with fan bases and like you could tweet right now something about pick an issue. I'm not even saying issue. You could, you could tweet about a divisive political issue and then your next tweet could be, the Cowboys will not make the playoffs. You tell me which tweet is going to be more just visceral, just anger. Even if one tweet gets more replies. I just think sports fans, like, they're the ones to me that will actually show up to fight, God bless them. And I think part of that is also because sports brings you joy. So when you're insulting a team to a degree, you're insulting the fabric of someone's being. And I think they take that a little bit more personally than they do. You criticize and whatever politician represents their party.
Host
I have said for a while now that what sports do to people because you don't jump up and down screaming at many things. Even if you're in the delivery room when you have your child, there aren't many things that give you permission to do that with joy. And it's been a weird world to occupy, at least in part because of what you're talking about. Some of those rigidities almost don't allow somehow for funny. Which strikes me as so weird that. That sports television wouldn't be funnier given what we're covering. Like, it seems like such an easy place. I've always been mystified by this, that this playground is taken so seriously that even if you're a little off kilter like we have been, you're viewed as sacrilegious because you're not treating it seriously.
Roy Wood Jr.
How dare you smile while doing any of this. You can't even smile while playing sports. Half the time they'll say that you're an. I mean, when you look at the marriage of those two industries, how often does that even happen? You had Sport Night on ABC back in the day, which was like an ESPN 30 Rockish type show, but there's not a lot of comedy set within the World of something professional, not with a professional logo on it. And then when it's not a professional team, well, then you're in wackyland. Because then the fans don't really. They won't accept that.
Host
I thought Jay Moore had a shot originally at espn. I don't know when he was doing a comedy late night show in its original iteration. I don't know. How long ago did that predate you? Too much?
Roy Wood Jr.
Yeah, that predates me. You know, I remember the program, but I wasn't an LA comic yet, so I didn't have a relationship with Jay at the time. But I just think it's a very difficult place to land a plane because you're going to. Good comedy is going to piss off somebody and there's nobody more sensitive than people within the orbit of sports. And they're going to complain to some exec who's not going to stand beside you because ultimately they could replace you with anything because it's cheap. So it's not worth the battle.
Host
Even cheaper now, right?
Roy Wood Jr.
Correct.
Host
It wasn't expensive before and it and all of us were almost totally disposable.
Roy Wood Jr.
Even if it's.
Host
You could have replaced it. You could have whatever Sports Nation was. Yes, it might have been Michelle Beadle and Marcellus Wiley. But if I put you on there with ESPN Person du Jour, by virtue of it being on espn, it would be cheap programming that would make money easy.
Roy Wood Jr.
Yeah. Same thing they did with the Jump. Bye Bye. Just because like they, they like. Even if it's a hit, like when you look back and this wasn't a comedy. But I will go down. I will take it to the grave. That playmakers. Oh, one of the best television dramas ever written.
Host
So good. The NFL stomped it out.
Roy Wood Jr.
Yeah. They said, you better get that show off the air. That's telling the truth about drugs and pain.
Host
Drugs and pain and sex. We can't have that on. On espn.
Roy Wood Jr.
Yeah, get that off the tv.
Host
It was shocking to see that on ESPN for whatever it was, four episodes or one season. And the NFL said, no more of that.
Roy Wood Jr.
Yeah. And the only place you could have put a show like that was on like True TV or Spike. Wow.
Host
I had thought that might have been because when I talk about espn, always people hear some sort of bitterness in it. But I always wanted them as a content company because the space is so valuable. I'm like, if you put a little more money into some of these things, like they could be special, different funny shows. Creative playgrounds that are wild, sprawling things. I Wanted to. And in the last iteration at espn, I wanted to do a daily show for sports with Pablo Torre and Mina Kimes and Bomani Jones. And it wouldn't have been that expensive by television standards. But if they can make it cheaper and if they can pay everyone, you know, $100,000 a year, then. And. And if we're all actually interchangeable. Right. Because we are. We are. It doesn't matter whether it's Kendrick Perkins or Bomani Jones on espn. I mean, it might matter to you or me, but it's not going to matter to what they're doing.
Roy Wood Jr.
Yeah, I think the biggest difference between. I just feel like sports and entertainment have always overlapped, and if you understand one, it helps you understand the other. I'd say the biggest difference, though, is that, like in sports leagues, the owners want to pay their employees. You know, they may pinch you a little bit here and there. Whereas the difference in entertainment, if we're comparing the owners of sports teams to the heads of studios who run all of these companies that. That green light or cancel all of this stuff, they don't want to pay anything. They're constantly looking for a way to cut a corner and make things cheaper and pay everybody the league minimum. Whereas in professional leagues, you have supermax deals and guys who barely see the court getting 80 million and 90 million for two years. So you'll never see that in entertainment. Here and there, there's, you know, there's a couple whales who get a real contract. But, you know, for the most part, the strike is. It's about the 85% of actors that don't even qualify for health care. You know what I'm saying? But the strike is also weird, though, because I think it's not. I think that the public sentiment for the writers and actors, it's grown. It needed time to grow. Because this strike isn't as instantly impactful to the average US Citizen as is a teacher strike or a transit strike or sanitation. Your neighborhood starts stinking and you gotta walk to work cause ain't no bus.
Host
We'll feel it in 18 months or 24 months when the content dries up.
Roy Wood Jr.
Correct? Correct. Well, not even that long. I'd say maybe January, but.
Host
Oh, wow, that quickly.
Roy Wood Jr.
I think at some point. But it's. As the voices start permeating, it just takes. This is one of those strikes where I feel like it takes time for the word to spread, for people to really understand, for people to really be educated on exactly what is happening. Because your perception and assumption of an actor is that they're all balling, because you saw a couple of them balling in a newspaper or in an article. So you assume that all actors live fat, like the top 5% of actors. And that's the difference between a teacher and a garbage strike. You know, ain't no teachers balling. There's no teachers with a Porsche. And if they. Are they stealing, stealing from the school. So you can't go, well, don't they all have Porsches? No, you know, they don't all have Porsches. You've never seen them. So, you know, they're all struggling. So I think that's the biggest difference. But, you know, I just think that if industries, if sports were to not take itself so seriously, it would take one quadrant to not take itself so seriously, Be it the journalists who don't want to be criticized ever, be it the fans, be it the players, be it the owners. One of those four corners. If one of those four corners lets off a load and goes, ah, we can laugh about it, then it'd be okay. But it's too much money involved. It's way too much money involved.
Host
Your father made you want to be doing this because you were seeing his activism and radio love of journalism through the work he was doing, or were you not moved into this path by any of that?
Roy Wood Jr.
I wasn't moved. I was more inspired by Stuart Scott and Fred Hickman than I was my father in the beginning because my dad's work was more. He was a true radio news guy. Like, he went out and was embedded in wars, getting shot at with a tape recorder. Vietnam, Rhodesia, Zimbabwe, now South African riots, civil rights movement, name a riot in the 60s. My pops was there. So a man like that who then matriculates into working in Chicago at WVON and starting co founding what we knew at the time as the national black news network, nbn. NBN was essentially a news outlet, a national syndicated news outlet that delivered news for black people to let black people know what's going on. Here's the news that's relevant to us, and here's what this means for you. Here's what this policy thing means for us. You know, just being the news window between black people and all of it black owned, right? Correct. Correct. And when you take in, and I didn't learn this till later at the Daily show, but when you take in nothing but bad news and your job every week is to go cover the bad thing, then you just. I didn't see him laugh a lot. I'll just put it that Way I didn't see my dad laugh often, you know, I enjoyed laughter. Laughter was an escape because, you know, we moved to Birmingham from Memphis when I was in the third grade. And I was never in the same school system for more than two years until high school. So every two years I'm having to meet new people. And humor was the easiest. If I make this person laugh, he's not gonna fuck with me. So let me figure out how to make people laugh. And it wouldn't even necessarily be the bully. In the classroom, you identify the bully, but you identify who the bully's cool with, and then that's the person you go get cool with. And then by proxy, maybe you get the bully off your back. So, you know, for me, humor was more of a defense mechanism than anything. But it just came naturally. I mean, I play sports, but I wrote the bench. So you just. You're alone in your thoughts.
Host
You're just sitting on the bench about everything that's funny around. You're not playing, you're not any good. But hold on, I want to go back for a second. Because your dad is bringing joylessness to the work. That's what you're seeing. And understandably, right, because if you're talking about Jesus, like, not just covering the things with a tape recorder, quarter, you're talking, but also just coming through the. The racist south to.
Roy Wood Jr.
To just the PTSD of existing as a black man in that time, right? So it's like, okay, I can look at him and see that he's not well most of the time.
Host
Beaten down.
Roy Wood Jr.
Yeah.
Host
Fighting has to fight all the time because he has to survive the same way you do. You're going to do it funny to keep the bully away from you. Calculated, strategic. He didn't have those. He didn't have. The world buried him because he had than you did.
Roy Wood Jr.
So you either cop, so you either cope with that, with drugs or alcohol, or in his case, women. Like, that was the escape like you have to have. And now. And he also had a jazz show. He loved jazz. He would do all this wild cover, this, that, and the third, get mace tear gas, and it would just pop in John Coltrane. And that was like his happy place. So, like, I observed that and, you know, innately, I just tended to gravitate to people with bigger energy than my father. And then as I got older, then you realize how much of your parents is just in you. And there's not even anything you can control one way or the other. You just kind of. You wake up one day and you go, you know what? I don't want to keep making jokes about the weatherman and check engine lights. What's up with this police reform? Like figuring out to go from that joke to start tiptoeing into issues, but not even really trying to choose a side half the time. Just going back to the old radio rules. Find the alternate angle that no one else is first, do the research. Find the out everything that's been said about this issue from every possible zigzag. I go on Reddit and read all the weird message boards that whatever the lobby is to the dark web, let me know everything about everything and then from that, formulate what I think about this. But this is how.
Host
This is how. This is how a maximum hustler in this industry. This is why I admire this. Because you had to find all the slivers over 20 years. People think you just get between people that are naturally funny.
Roy Wood Jr.
No, that you're.
Host
That you're just there. That you're. This is a funny man, a holy man. Reached into his crib and gave him funny when he was young. And look at him. He's on television between those two people, choosing the perfect window to tell the joke. That's going to work as the. As the fifth voice because. Because you've sculpted. I'm going to get in and out of here with a sentence or two and not waste your time.
Roy Wood Jr.
That's all you need.
Host
But you've been. You've been. That hustle to survive for 20 years of career bounces through small comedy clubs at the beginning. Right? Like the. The hardest parts of this and maybe the most joyful were back then because it was.
Roy Wood Jr.
It's always more fun when it's early. And that's when you. You're not. You're not plugged into enjoying it. And you should. You should enjoy it.
Host
Well, you don't have the years of wisdom to know that then. Right? That comes with only time. Oh, I should have enjoyed that more.
Roy Wood Jr.
But you don't. You. Because you go to. You go to a room now. You know, back in the day, there used to be rooms that were turned into a juke joint after the show and you could stay and just dance and talk and just meet and interact with people. And I met, you know, to work in the south on a weekly basis and make enough money to pay bills. Like I'm talking, if you're trying to clear, clear anywhere from 25 to 40k, which was kind of what I cleared eventually as a middle at before I moved up to a headliner. We're talking 01 through about zero.
Host
$500 a show, $200 a show.
Roy Wood Jr.
Correct, Correct. Now they're not covering gas in between. And if you have an off night, you got to figure that out. You can lose 50 at a hotel room or you can fly and J it. Sometimes I would go get a. I would go do day later and use the money from day labor to pay for the hotel room wherever I was in that town. So you know, just get to the city a day early, show up at 6am with some work boots on, do a shift, come home at 5, go get a hotel room with my. So I mean there were ways to make it, to put it all together. But yeah, those were good times and I met a lot of people and a lot of great comics that I got to open for, I got to work with. And the thing that really is impactful about that now is that that a lot of those people, they've either quit or they've died, but they've made it. Just like knowing those are the three, those are the three lanes for comedian. Some suicide, some bad health, but you know, depending on the comedian you could almost akin quitting to dying if they didn't want to quit. You know, you, whatever life thing happened to you and.
Host
But that's why it's the hardest thing to me. That's why I'm saying I don't think people understand how hard you had it. It's a community of what? How many people right now who could pick up a phone and do a 50 city tour? How small is that world?
Roy Wood Jr.
I'd say if we're going across all genres, all races, I'd say about 500 if that. 500 comedians right now that could do 50 cities. Yeah.
Host
Or to make a living at it. Not truck stop, to truck stop, to make the. It's a very hard way to make a living.
Roy Wood Jr.
And there's no safety, solely paying bills off. Stand up alone, no other income coming in. I would say about 500. I could be off. I know some comic might argue a thousand, but I think at that point you're talking about Openers. There's not 500 comedy clubs. There's some theater venues, but not everybody can play at theater. Let's say everybody can play a comedy club. There's 50 states. You on the aggregate, let's just say there's three comedy clubs per state, some high, some low. So that's, you know what, 150 clubs, 50 times three.
Host
So there are how many people in the world who can appreciate how just how hard it is to do this, because if they're quitting or dying, they're not living to tell about it, right?
Roy Wood Jr.
Yeah, I'd say a thousand. I would say if we're counting open micrs and MCs and feature acts and stuff, I would say it's probably 3,000, 4,000 comedians that hold the title and at some point have been paid at least a dollar to do it. But of that 4,000, I would say probably 500 or so along the path.
Host
And given that the truck stops were the beginning and there was some joy in it because you were chasing something and it was better than jail. Has the industry beaten you down in a way that would in any way look like what your father was after 20 years of the industry beating him down? That you start with this idea of I want to make a living being funny, and then everything that happens in the industry is so stupid, unfair, greedy, silly, that you just get beaten down by it and it sucks some of the joy out of the fun.
Roy Wood Jr.
Well, then it also gets to a place. Where do you want to keep talking about those things? And I think that's part of why my dad did a jazz show. Like, I get that now.
Host
That's what you have to do.
Roy Wood Jr.
Yeah, you just have to go on.
Host
A touring jazz show.
Roy Wood Jr.
But that's what sports is for me, like that. I enjoy that because I don't have to sit and yell about world issues. There's a stress in that. And I saw that that through Trevor Noah, because Trevor, at least I had days off now and then as a correspondent. Trevor's in there every day hearing all the bad stuff and then choosing the stuff that we can make a show with that takes a toll. So.
Host
Well, what was that, by the way? You mentioned that earlier and I wanted to ask you a follow and I didn't about just. You said how hard it was for him. Not just following Jon Stewart. God almighty. Yeah, but just okay, who are you and why are you talking about these things?
Roy Wood Jr.
Who are you and why are you talking about our business? Where's our dad that we've loved all these years before you? And then meanwhile, behind the scenes, he's reading all of the most horrible shit on earth every single day and then deciding what stuff to put on tv and then getting criticized for that.
Host
Race and xenophobia. Not just race, like every kind of other.
Roy Wood Jr.
Don't revision his history. Trevor Noah, There was a lot of hate on him in that first year. A lot of unfair hate. And then it became love over time and repetition and just him working and just doing what he does and people eventually coming around but out the gate. It's very hard. And I don't think the next host of the Daily show will necessarily have to deal with as much of that from the outside. But internally it's still a very difficult mind bending job to just sit and take all of that in and it is exhausting. And at some point it gets you coming home with a thousand yard stare like our fathers it And I don't know if that's what I would want. Is there another show option perhaps. Can you, can you pepper in some other shit in between the segments to like that's where my brain.
Host
Oh. But I just think one of one of the reasons that I would advocate for you doing this show, you tell me if I have any of this wrong, because they're just observations from afar, but because you realize that the platform that that is for you to be able to do that show in your voice, your way by hiring just a handful of people who can put your imprint on it. I can see you doing that show with your experiences and your growth in a way that's super uncommon for anybody with real confidence, with real confidence to be yourself on television. Because you know this playground and you'd. That's why I think you'd crush it, because you would imprint it. And you, you've been working all your life for this moment.
Roy Wood Jr.
I'm thankful and I'm appreciative of that perspective. I done a lot of things that would say that I could do that thing. Well, now you have to convince an exec who does not want to take chances in a time where pretty much every studio wants to do the safe thing. They want to do remakes. They don't want to rock the boat. Because if you do something truly different and it doesn't work, it's your ass. You have to convince that person to do something different. Because what's wild is that everything that you're talking about with me, that would be considered a radical approach to television by some studios.
Host
But you would play with the form by zigging when others are zagging by put you've been doing that all your life. You have been looking for the spots when you can. If I gave you, if I armed you with a team of writers right now and said do a political show, that okay, it has black in it. But no, that's not. You're doing a show for everybody that has broad appeal. You are uniquely qualified to win Walk to walk that tight rope.
Roy Wood Jr.
The shows in Late Night that we respect the most, that have done the best, were done by people who the execs did not get in the way of. So the question becomes, will people creatively obstruct me and keep me from doing the things that I want to do that best fit me? Because let's not get it twisted. There's some shows out there where people want to hire you to do what they think you should be doing. They don't want you to be you. I look at you, and I think you can be a good version of what I need you to be. So let me just take a little bit of that creativity away. Let me knock away that little part of your person out there. Now you're perfect, and now you're miserable. Ain't tell Conan what to do. They didn't tell Arsenio what to do. They tried to tell Trevor what to do, and then Trevor told him what the. What the fuck we gonna be doing? So, you know, that. That part of it I can't control. And I'm not going to just accept something if it means that, like, would you drive a Ferrari if somebody else was controlling it remotely? Yeah, it's a Ferrari, and you got a Ferrari. You had a Honda, but now you got a Ferrari, but you have no control over whether it's turning left, whether it's turning. They decide where you go in the Ferrari.
Host
I'm a bad person to ask, though, because I left the Ferrari because they took one bit of control away from me, and I just, you know, I just. Yeah, I got. I wanted no interference. I didn't think I was doing anything that was that blasphemous.
Roy Wood Jr.
We are at a time in entertainment, sports as well. We are at a time in entertainment where talent to some degree can dictate what they want and what they want to do. And the execs don't necessarily have all that power. Which brings me back to that original point about Pat McAfee and that it used to be a setup where, hey, I think you're talented. Come with me. I'll help you find an audience on my network. Now it's more of a. Oh, I see you have an audience. Would you like to come be on my network? And that's not a knock on Pat. You built your shit. Go get your brick. But I think that has a true. That is a true viable path to all of the other things that we thought we needed a degree to go and get. And so now we're at A time where you have execs across all these networks, they're all going to have different financial mandates. And who knows how much money the writers and the actors are going to get when we settle. But when we do, it's going to change some financial models. So when those models change, your priorities and your creative goals are going to change. And what are those creative objectives from the networks versus the creative objectives from talent and people like me and going, no, that's not what I want to do. This is what I want to do. And either you with it or you not. Or you go over here and you fucking build your own shit. You pull a Levitard, Build a studio, put some Neon up.
Host
That's right.
Roy Wood Jr.
I don't know if I can afford.
Host
All this just Neon. Yes, we spent. We spent a lot of money on the Neon and we blew these entire budget on the Neon. You really admire it sounds like Trevor Noah because you saw close up how unfair all of that had to be to try and navigate that comedic.
Roy Wood Jr.
Yeah, I mean, but it's America, you know, we judge foreigners harsher out the gate. That's just what we do. Who are you to come here and to, okay, I like you. And that whole sentence took about five, six years. We didn't get an Emmy nom for five years as a show. I think when we won, it was for digital. Like the actual show itself didn't get a nomination for a while. You know, it's just people looking and seeing and trying to decide what he was doing. I don't want a show that puts me in that place. I love Trevor Noah, but you don't quit live on the air because shit's going good. You know, you step down because you realize you're ready for a change. Well, then there had to be things that incentivize that type of change. So doing a job that meaningful, there is going to be stress. There has to be. It's a show every day that's not easy to do. But what I'm more. What I'm trying to be cognizant of as I grow is figuring out just how much of myself I want to lose in all of that. Because I don't want to be the guy that's just yelling about government every night. There's other things to yell at.
Host
It's interesting because what I hear, you. Correct me if I have this wrong, because you're in the running for a job that would have safety in it, that would allow you to raise a child without being in 50 cities over the course of a year away from a child that would offer security. And it sounds like what you're saying is it is possible that they give me all of these things. That would be the dream scenario. And I get there from one day to the other, and as soon as I land, I'm unhappy because I realize that the people I'm working for are not going to allow me to do this the way that I want to do it. Or worse still, I'm going to get a little bit of turbulence and they're not going to support me. I'm going to get inevitable turbulence when I start, and they're not going to support me. And it fizzles in six months because as a black man, I have this much margin for error.
Roy Wood Jr.
I agree with all of that. But the option also still remains to just go and do your own thing. And everything you're saying could also still happen. People go, oh, yeah, we like it. Yeah, we'll do whatever you want. And then you show up. Slight relationships.
Host
Yeah.
Roy Wood Jr.
I don't have a problem with you staying out late. Hey, why are you always out late like that could be. It could be either way. I just think that going into it thinking that, and this is for anybody that's trying to do late night, going into it thinking that whatever you're going to get get will mirror what was before. COVID you are mistaken. The creative taste of people are different. The cre. The fiscal access is different. They're replacing James Corden with a game show. And it's not because At Midnight isn't entertaining, but it's also because at midnight is cheaper to produce than the late Late Show. That's what they think about late night. Tradition don't mean shit. Money means everything to those entities, to those stockholders.
Host
It doesn't mean that they're wrong, though, that it has changed so much. Late night has changed so much that they can throw a game show on there and people are just catching clips in the morning anyway.
Roy Wood Jr.
You're making, for the most part, you're making tomorrow's Internet today. So how do you make this more relevant in the now? There's not a lot of lives live TV events that I think people clamor for that are non sports. Like I would say the White House correspondence dinner. Still, that's still a relevant live thing. I wanted shows.
Host
I wanted to ask you about doing that because I feel like if you can do that, you can do just about anything.
Roy Wood Jr.
Yeah, but the correspondence dinner, nobody was in my way and I had my team of Writers who understood me. So I think that's, you know, I think that's a degree of what you need. But I think networks and I think talent are both trying to predict what late night will truly look like on the other side of the strike, and then that's when the good ideas are gonna flow. I don't think the Daily Show's going to go anywhere, regardless of whether or not I'm the host. But it is going to creatively evolve. It has to, or it will die. The same as any other show that can evolve, evolve. It has to fiscally evolve. Like, that's just.
Host
But this is what you're looking at, right? This is.
Roy Wood Jr.
You're looking at my light in the end of the tunnel, coming to run me over. I'm not looking and going, ooh, I might get the host. It's going. If I don't figure out how to fix that show and do I need to come up with an idea that is me, that is affordable, that I can do every day that doesn't stress me the out that's also funny and poignant and fresh enough that people would want to watch it on the day, not tomorrow on the Internet.
Host
All of which you can do with 15 writers. 10.
Roy Wood Jr.
10, I don't think. Well, I don't know. Depending on. Depending on the guild, there's gonna be minimums that you have to carry for late night. I know right now, Daily show, we carry a pretty good. We got a deep bench, but we had to because we had a bunch of.
Host
You would be inspired. Would you not? I know I can get your eyes to twinkle if I tell you 10 writers, go do your own show. Do it the way that you want to.
Roy Wood Jr.
Yeah, if the guild said 12, I'd rather have 12. I think the guild is going to say 12. I think that I don't know all.
Host
But you don't need 12. But you don't need 12.
Roy Wood Jr.
I don't need 12.
Host
You might be able to do it.
Roy Wood Jr.
With eight, but if I say eight, then everyone's going to do it with eight. And then you. The whole.
Host
But this is how you have. But this is how you have to think right now, man. Look, 20 years, you figured out how to hustle your way to money through evolution. In this business, it has changed for all 20 years, and now it changes again in a way that's even more dramatic, more seismic. And you are now living a bigger lifestyle with a child that has different responsibilities.
Roy Wood Jr.
Correct. But then there's ways you can play within those margins. Right. Where And I don't want to get all David Sampson, how to finagle the salary cap type shit. But I could carry 12 writers and if that's more money, then you could shoot two episodes on one day and save a production day. Like that's one way to get, like that's what a lot of daytime, like daytime talk. But they do that because their shit's evergreen.
Host
So if I gave you, I, I feel like if I gave you just the skeleton to create a budget for this show, you can come in. Why are you creating bare bones? I'm just saying that you. I believe, I believe that I wouldn't have give three writers to make a good 50 minute show.
Roy Wood Jr.
What if you did it like leno in the 90s and just had strangers fast and if you use the joke, give them 100 bucks. That was a true thing, by the way. Well, but the Tonight show had writers, but they also just had random comedians across the country who would essentially Tweet back in 92.
Host
Right. The reason, the reason that I wanted to talk to you about some of this stuff is because you appreciate the industry enough and the history to know that Jay Leno was hiding in a closet when some of these decisions were being made by executives whether it would be him or Letterman to replace place Carson. You come in as a new age of comedian on the funniest daily show that there is that replaces Carson in some ways in America and gives makes a network matter. Because what you guys were doing, people were hunting it down.
Roy Wood Jr.
You think it has to be as fresh as possible. I think the biggest, I think the biggest hurdle in my opinion for late night as a whole is that it records too early in the evening. Evening. I think that's one of the biggest problems is that you're recording a show at 5pm to go on at 11. And that's not just Daily Show. Seth, Jimmy, every. Everybody records early and Jimmy Fallon, not Kimmel. I don't know what time Kimmel. I've never done Kimmel. But I think that making something closer to airtime. If it's more expensive to go live live, then don't go live live. But there has to be some degree of freshness to the content. The conversation needs to be as prevalent and fresh as possible.
Host
Well, it has to evolve to the modern age in a way it hasn't.
Roy Wood Jr.
Correct.
Host
Like what you're talking about is you're. If you're taping something at 5pm it can be dated now correct by 11pm in a way that it couldn't be.
Roy Wood Jr.
20 years ago live like that anymore. That's the first. That's the one change. Any program that I do that's late night, it has to be live or damn near live. The only thing that's closest to damn near live is the Breakfast Club with Charlamagne and Envy in the mornings, they come on BET at 9am and what you're watching at 9am is stuff that was said at 7am it's less than two hours. The content's not even two, three hours old, and it's already on air. That's being on top of the conversation. That's being ahead of the curve. And I think that's where late night eventually is going to have to start. Going to the other issue, in my opinion, if we really want to fucking pop the hood and find I can do a diagnostic, is I also think that the places where young people get their news doesn't always mirror the way in which news is parodied. Does that make sense?
Host
Yes.
Roy Wood Jr.
So when you look at regular tiktokers rocking down the street that are spitting real knowledge, and then you look at a lot of different podcasts now that have viewership that's higher than some local newscasts in certain markets, those vehicles, the visual medium of that matters. Flip that shit. Parody that. And the thing that's weird is that I don't imagine the tiktokers and the podcasters would be as offended as the local media would be for being parodied because they come from a different comedic sensibility. So I think that plays like, when I look at the type of show I would want to do, I know the win and I know the creative visuals that I would kind of, you know, sprinkle in there.
Host
But you wouldn't be given the freedom. Right? The only way you can have the freedom is to do it all yourself, probably.
Roy Wood Jr.
So unless someone came in with a disgusting amount of money or a disgusting amount of true trust.
Host
But if you put five of your comedian friends together in a room, you would dominate the sports podcast market. If just you and a couple of your comedian friends, you and Neil Brennan decided to.
Roy Wood Jr.
Neal's a good friend.
Host
I'm just saying, like, you guys are a lot funnier about sports than the people I talk to every day.
Roy Wood Jr.
We literally, we text them every day.
Host
About sports ironically, and how stupid it all is. Because you've sort of outgrown it. Both of you have. You've learned some things in adulthood that make sports this funny little thing that exists over there that comedians would have a good time Parodying in a way that would get audience very quickly because there's so little, weirdly, there's so little funny in this medium. I don't even get why there's so little funny.
Roy Wood Jr.
Do you think the. Do you think sports journalism has benefited more or less from the flood of podcasts from athletes? I like it. I think that some are better than others in terms of the journalistic structure and the conversations they're trying to have. Have. But I admit I've kind of enjoyed seeing active athlete. And it's predominantly basketball. It's not really a lot of baseball. I think football had I am athlete. But I think they broke up.
Host
I love how competitive all of this stuff has become and the meritocracy and athletes flooding to it with understanding. Many of them will get weeded out. It'll be survival of the fittest, just like it is in sports. If they're not actually working at it, if they think they can just get on a microphone and talk because they're famous and that people will keep showing up like it's.
Roy Wood Jr.
If people know when it's mediocre. Mediocre. Even if they can't identify why they know when they're getting split.
Host
Travis Kelsey said podcasting is the hardest job in the world. And I'm looking at what he's doing. I'm like, what's the matter with you? What kind of. But, but the idea of having to. To be excellent at it. Not enough of them care that way. But all of them has seen what's happened with McAfee. If the punter can do it, if the punter. But what he has done is he's created a community around, you know, not nine dudes he's frolicking with and he's appealing to middle America and he's not doing any of the stuff that's gonna bother Disney because it's gonna get headlines in the political or race realms.
Roy Wood Jr.
Yeah, but I think that. I think a lot of the athletes, though, they tend to be more open with one another. And I wonder if that's because they have a familiarity with the person across the table or if traditional sports journalists aren't always as. As chill because they are all default into button down mode, which makes the athlete button up, which makes him not tell you the good stories.
Host
Ed James. I remember being in Immokalee with him and he's in his Bentley and he wasn't telling his story to anybody. He's like watching Scarface on the television of his Bentley.
Roy Wood Jr.
What year is this? Is this straight after you.
Host
Yeah, it's. It's. No, he's had a couple of good years with the Colts, so he's a star, but he hasn't told anybody his story. We ended up putting him on the magazine, in the magazine cover, like, in a way that scared shared America with, like, just gold teeth and dreadlocks and everything else. And he was giving his first interview where he was talking about things like, yeah, I'd ignore my coach if he said to Neil here in this situation if I've got incentives in my contract that pay me for touchdowns. And so I ignore Peyton Manning and everybody.
Roy Wood Jr.
And.
Host
And because I there don't put it in my contract if you don't want me to ignore the coach and go get the money that's in the end zone. But he took me to tell his story because he trusted no one and I would do well enough to get close to wherever he was while not being able to get close there at all. Not at all. Right. He was selecting me as the journalist to tell his story because he's looking around and didn't feel like there was anybody who looked like him who would end up telling the story. And there's all sorts of muddle between. The athlete doesn't trust us. I don't blame him. The athlete generally doesn't have very much in common with us. And of course, if I put you in a with comedians, you're going to probably enjoy the conversation with all of the connection points about comedy than if I just put you in there with any kind of journalist asking questions.
Roy Wood Jr.
Yeah. So then how do. How do news outlets compete with that? Then how do you compete with an athlete giving more to a podcaster than to your own reporter? Because some of that stuff is as the conversation on some of these podcasts are as good. Like some of the JJ Reddicks that JJ gets out of my. It's as good as stuff that would be on on a Sunday morning.
Host
He's working at it, though. It's not just that JJ is sitting down with somebody and they respect JJ because athlete X is looking at JJ and saying, you couldn't have shot 40% from three. Unless you really care deeply about the way that I care about this sport. You are excellent at what you do. The respect is built in. And then JJ treats it as like, how do I get content out of this person? By just having a barometer for what's interesting.
Roy Wood Jr.
Are there any athletes that you found that liked criticism? Criticism? Because I know they don't like it and probably that's part of why they probably go talk to their buddy who they used to run with in G League.
Host
I wouldn't say, like, criticism necessarily, but I do know that Barkley is one who just is immune to it. Has. Has developed the skin where it wouldn't.
Roy Wood Jr.
Take the interview off track. Like, when you have the one or two criticism questions you have to eventually get. Get to.
Host
With Barkley?
Roy Wood Jr.
No, with any. With any athlete. Like, were there any athletes where if you criticize them, if you brought up a fair criticism within the interview, then you would see their energy shift and then the interview is basically done, or it's. Or it's not the same.
Host
Are you asking if there can be an intimacy in an interview where an athlete is actually welcoming a criticism he or she hadn't considered because it is constructive and would therefore be helpful?
Roy Wood Jr.
Correct.
Host
Does it strike you that that's the dynamic in sports interviews?
Roy Wood Jr.
But, see, I could do that with a politician. A politician wouldn't care. Not the real ones, not the ones that, like career politicians. They're. They are already. They're prepared.
Host
You've seen. You've seen this machine so deeply from the inside, how silly a game it is. Even you have to be surprised by what's happened over the last six years in this country.
Roy Wood Jr.
You know, you want to talk about the correspondence, Jenna? You know what was really wild was going to the after parties and just seeing all the people that be yelling at each other on tv, just drinking and kicking it, and I'm like, what the. What is you drinking with him? You talking? Weren't y' all just on the. Oh, oh, y' all all friends? Because you used to work together on the thing five years ago when that network wasn't as divisive. And now you have to choose a side and you have to feed your kids. Kids. And it's just the equivalent of them booking their 40 cities, just like, I gotta eat.
Host
That's not happening with Draymond and Jordan Pool.
Roy Wood Jr.
No, I don't think so.
Host
It's that overt, though. It's that brazen. It's that brazen a grift, that they're all professional wrestlers just stealing from us.
Roy Wood Jr.
Yeah, but nobody would believe it if you told them. And then also the general public, the lie is more complicated, comforting. So I don't want to accept the truth, because then that means I have to unpack everything I've ever believed and then reprocess. It's too much work.
Host
So you haven't been surprised by the.
Roy Wood Jr.
Last six years not particularly. But then I also had a father that took me around to every Democratic primary. Like, I remember, I can take it back to 84. My pops had me backstage with Jesse Jackson when he was like, debating Michael Dukakis. Like, just, I've seen it all. I've met these people and, you know, some of the politicians, Democrats as well, not always good people off camera, off stage. You know, some of those people over the years, you know, you have to remember my father, he covered a lot of politics and a lot of civil rights leaders and a lot of people who were relevant to the black cause. If those people came through Birmingham, they came to the community crib. So I hadn't seen him in, you know, I'm middle school. But I can reconstitute it now as an adult and understand what the vibes were. You know, like, not everybody was, I'm not going to say they weren't noble, but I think that there is definitely. Well, what can I get out of it? First ism. Within most politics, you didn't realize how.
Host
Politicians, you didn't realize how dumb that was. The while backstage on Jesse Jackson and Dukakis. Right? You're two young.
Roy Wood Jr.
No, that's, I'm learning. I'm a bill on Capitol Hill and everything's great. And we elect a president, gets the most votes, and then you get to college, Electoral college, dangling chads. But like, we were. I was in the group that marched when Jeb Bush wouldn't certify the Al Gore, blah, blah, blah. In 2000, you get older and you go, wait a minute, this feels like a hustle. Oh, you're redrawing districts? Are you gerrymandering? Didn't learn that Nadia. Before, it was just vote, and then more people vote and you win. It's like, oh, okay, even when you're in office, you're still, you know, a lot of people, you know, running hustles. You know, I, I, I spent time in, in black barbershops where, you know, you hear grown men conversations as a middle school, as a high schooler. So, you know, I understood how city politics worked in Birmingham. And once I understood local civics, I just kind of took that and, and just applied those assumptions to state and national politics for the most part. And for the most part, I've been right. You know, it's not really, you know, like, there was a then mayor of a Birmingham suburb, eventually became a mayor of Birmingham gentleman named Larry Langford. And Larry Langford at the time was trying to build an amusement park in Birmingham park proper to cut off traffic from miss. People from Mississippi were coming through Birmingham to go to Atlanta to go to Six Flags. So Lankford's idea was, let's build our own little thing here and maybe we can siphon some of that traffic boosted tourism, blah, blah, blah. But Birmingham has like, I don't know, I'm just spitballing. Let's just say there's 10 suburbs. Each suburb has its own mayor, but they're all part of the county commission within Jefferson County. So Birmingham, Princeton proper is not liked by the other outlying suburbs. If it's good for Birmingham, the other suburbs. And Larry Lanford came in that barbershop every day for about two years and just gave the play by play of where he was on trying to get the other suburbs to play ball. And eventually he got the deal done and Vision Land was built. Alabama Adventure, now it's still there. Wonderful park, go there. All wooden roller coaster, beautiful wave pool. But just as. As a high school student, listening to this man talk about just trying to get all of the suburbs to agree to put in a little money to build a fucking park, to bring in money so we can split the money amongst all of the municipalities and we all grow completely other bullshit. The type of stuff he like just cutting deals and having a meet and going to talk to, you know, it was. It was a, like, that was like my first lesson in local politics from a dirty level where, oh, okay, for this guy to approve it, you got to go do these two things. And this guy, he'll like, stupid. Like, I need Alabama tickets. I want to meet Gene Stallings at the next. I know.
Host
Yeah, I gave you a couple of tickets to an 8 and 4 gene stalling.
Roy Wood Jr.
Literally. Literally stupid.
Host
But I mean, I can't imagine what it was like for you or where your imprinting from Birmingham resides.
Roy Wood Jr.
It's a great city. It's a great city. And I think that Alabama as a state, there's always going to be some pockets of BS in a lot of different cities, but I think we assume one spot to be like everywhere else or be like, you know, we've had great mayors over the time, you know, that'll try to do the right thing. And then that gets struck down by Montgomery. You know, they tried to pass. They passed increasing minimum wage to $15. And then the state struck it down and said, statewide minimum wage is $10. Like, they just. For no reason, just, you know, because they could. Yeah. What y' all up there doing? Y' all trying to be good? No, shut that down. What y' all doing up there? Y' all trying to take down a Confederate monument. All right, $30,000 fine. Just little stuff just to poke at you. But it's a resilient place, man. I think people come together. That's why, like, even when you look at. Like when you look at the Carly Russell situation back home with the. The young woman who faked her own kidnapping for God knows whatever reason, I'm sure. Sure. Clearly some mental stress or whatever the hell she came out and said, she lied. Okay, fine. But if you look back at those first two days of when it happened, that whole community came together and looked for her. And I would pray that anybody is blessed enough to be from a city or a place as communal as Jefferson County, Alabama, where everybody came out black, white, white, whatever, to literally just walk through a forest for a stranger. Alabama is also that. You make sure you say that when you start talking about all the policies and you start talking about all the laws and stuff that really we don't have that much control over because the way the districts are drawn. So, you know, when you talk about the goodness of a place or whether or not a place is meaningful, well, we don't treat anybody from our community as if they're displaced, disposable, even if they might be lying. And there's a nobility to that. And I think that's something about Alabama that I think a lot of people get wrong, because those are the stories that people don't see. Those are the stories that don't get thrown up on the television, you know, as quickly.
Host
But how are you imprinted by it? Because it sounds like some fierce Birmingham pride is coming through there, as if. As if America misrepresents what a community is because it can be good at its core and then be corrupted by everything around it.
Roy Wood Jr.
Yeah, I think that, you know, Birmingham has given me a lot of pride in my blackness. It's given me a lot of pride in fighting for equality and what's right for me. What I've always tried to do with my comedy, though, you know, I'm not Dick Gregory. I'm not Paul Mooney. I'll never be. I'll never be in that. In that orbit. But if I can make you think just a little differently about something that you thought you knew, for me, that's enough. I don't know if I have the power to change your mind about it. I don't have the power to yell at you about it. I don't have the power to make you feel guilty about it and still make you laugh. And that was the brilliance to me of Paul Mooney and Dick Gregory was that they could get into something far more emotionally visceral and then yo, yo, that shit two sentences later into a punchline.
Host
I don't know anything about Mooney other than these two things I'm about to. To tell you, which are that other comedians admire his style of comedy. And also that he was very hard to get along with.
Roy Wood Jr.
Yeah, yeah. I mean, I never worked with him outside the comedy clubs. He was fine. But I have heard, you know, professional stories, you know, studio execs or the writer couldn't get this, that, and the third, I couldn't speak to that. But, you know, he was always kind and treated me with respect.
Host
It is possible that he got beat down so much by doing by the industry that an unhappiness was brought there.
Roy Wood Jr.
I'm telling you, I heard the same. I have heard the same stories about him. I don't have a personal story in that regard, but, yeah, you definitely look up one day and you're stressed about all of this. But, you know, I've never been. I've never been negative in that sense. You know, my dad, I remember one time in the seventh grade, I was in a dunking booth for our soccer team and gets raised money for uniforms. And my pops found out and he came and he cussed me out in front of everybody. It was like, just. I got straight undressed by my pops in front of everybody about, you don't make a fool of yourself. Because it was a. It was a fairly mixed situation. And there were some white people that were throwing balls. There were black people in line too. But he turned that corner. He saw that white person trying to duck a black kid and was like. And he just, he just said, you know, it might be. It might be a joke to you, but it ain't a joke to them. And I never understood that till, like probably a decade and a half later. But he just. He was not. You can raise money, but you're not gonna raise money like that. You're just not gonna let people do you like that. You gotta have some self respect. If you're gonna joke, you gotta have self respect. To this day, I don't know if my pops would approve of my career until, like age 33, like, when I started talking about, like, real shit. Stop doing jokes about gas prices and student loans, which I'm sure he didn't care about. But no, I. I think that, you know, Birmingham is just a place that Alabama is a place where, if you're not from there, I can't trust you to help it. I don't know if you're going to. So let me go and see what I can do, you know, So I try to do. You know, I do stuff with various charities down there. Too many to name. Meta gave me a bunch of the headsets, the Oculus things we got with Meta and Win Reality to baseball VR, batting practice, and they put the software on them shits for free and went and gave them back to my high school. So y' all can learn, you know, donate to. To the school resource center so the other students can just web 3.0. If I don't do it, I don't know who's going to do that. You know, in a perfect world, I would love to do more of that for all of the other schools in the. The city as well, but, you know, it just takes time. You know, it's just bit by bit. So, you know, it's definitely a place that's special to me and that. I don't even think that my final chapters are written there. I don't. I don't think I'm going to be in New York the rest of my life now. I don't want to move. I don't want to.
Host
But you talk about it with a longing and a love that I'm guessing you don't talk about any other city with because it sounds like you're. It sounds like the roots beyond you of your family structure and what they cared about, that everything that you loved comes from there and that you had to get out of there in order for your career to blossom. But it doesn't sound, from the way that you defend it, like it's a place that you ever wanted to leave if you could do all the things that you wanted to do anyway.
Roy Wood Jr.
Yeah, if I could have done it from there, I would have. But the hardest thing is to realize you can't and then go do it somewhere else, then come back and give the rest of the recipe to all the others. Like, I feel like a bee that went and found the pollen. And every now and then I go back to Birmingham and I do a goofy dance so you can know where the opportunities are.
Host
I remember being caas, you mentioned sort of the economy of what Hollywood is and how it's run by a bunch of middle managers that'll squeeze all the juice out of the industry. I had offers in Los Angeles and New York to do stuff and was told, like, it. It can't happen in Miami. It's not a thing that can be in Miami because you need to be in one of these other places. And So I was CAA's worst client for 10 years because I refused to do it anywhere other than Miami because I. I wanted to be tied to exactly what you're talking about. There's no other city that I talk about that way where I love it because I see things that you don't. And I know it's a bejeweled dumpster, but I know where the jewels are. And. And. And I know because I've lived here for 40 years. And.
Roy Wood Jr.
I had that same conversation with Comedy Central 2018. I had a comedy. I had a sitcom pilot, Jefferson County Probation, where I played a probation officer. It was based on a probation officer I had who was, like, super dope and helpful and just literally was one of the most important characters in my life at the time and helping me grow. So what would the criminal justice system look like if recidivism had people that actually cared about you not coming back to. To prison? So I went to Comedy Central and I said, I want to shoot this show in Alabama. I think the South. Each Southern city is uniquely different in that it can play a character like the way New Orleans as a city is a character within the show. There was a sitcom on Fox. Dig for it. It was Anthony Anderson and I think Cole Hower, and they both play. It was a buddy cop comedy set in New Orleans. Fox Early Arts, K Town, K Vile. My memory's amazing. The way they use the specificity of New Orleans as a character in that show was beautiful. The way Hustle and Flow uses Memphis as a character, the way P. Valley uses Mississippi. Like, I wanted to do the same thing for Alabama, and I went to Comedy Central. I talked to them about it, and they're like, well, Atlanta's cheaper. We can cheat Alabama. I go, yeah, you can, but you can't cheat Alabama. And there was about $200,000 differential in production costs, which is a lot. That is a lot of money to not shoot. Atlanta was 200k cheaper. So I go to Birmingham, and I spend about six, seven months in Birmingham. Birmingham just talking to all the people I needed to talk to. Basically pulling a Larry Langford amusement park move. How can we get the county on board and let me go talk to this guy. What is this guy? And it's just literally all of them.
Host
You were Larry Langford. What a plot. What a plot twist right there. You're. You're making Deals between the suburbs to see if you can get $200,000 reduced to get something to be more authentic and less corporate.
Roy Wood Jr.
Hey, county commissioner, I need you to. To make sure that we get this tax incentive for this thing that's going to be good for the county. We're going to use. We're going to rent equipment from this spot, and then you go over to this spot. Okay. We're going to use a caterer from this spot.
Host
And, like, we're going to help the local economy.
Roy Wood Jr.
And we did. We had 90 people on staff. 63 were Alabama residents. 13 in Cast. 10 were either Alabama residents or ties to the cast. Like, legitimately put money back into the city. You know, the mayor of Birmingham, Randall Wooden, he was integral Donald Loophole. Like, so many people came together for something that was inherently to shine a positive light on the state of Alabama. We ended up doing it for cheaper than we would have done in Atlanta. We beat the 200k show didn't go because of COVID And the Viacom merger happens, but hurts you like a dude. I was down in Montgomery. We had created.
Host
How long did that take you? That seems like such a cool project. And it just all gets wasted, right? That. That's happening so much in the industry right now.
Roy Wood Jr.
It took me about a year to figure out. And I'm going to Birmingham once a month, just spending three days.
Host
Just put in a library somewhere. Like, you've got something that's good. And it just got bought because why? Like what? Or it just got.
Roy Wood Jr.
We merged, we rewrote. We didn't like the pilot, so we want to rewrite it. Oh, the person who's in charge of your project got fired during the merger. We'll find a new. Oh, Covid hit. End of COVID Oh, we're not doing scripted stuff. We're getting rid of everything on Comedy Central except for south park and A Daily Show. But, hey, that was a good project. Good job. Let us know when you have your next idea. That's it. And it's dead. That's the game, bro.
Host
That's so heartbreaking, dude. Like, I mean, that's the game, bro. Like, you poured your heart into something you had.
Roy Wood Jr.
I should have poured my heart into this. That should have been the second project. Maybe my mistake is trusting on the first project, but I also didn't pay enough attention to the way to which way the winds were blowing in the industry that that show was never going to get more than two or three se. The shows that got greenlit over us died after Two or three seasons, and they got eaten up in the Grinder as well. So, you know, I don't know, maybe I could buy the show back from the network. That's the crazy thing about. That's the crazy thing about the entertainment industry is that you have to, like, if they give me money for an idea, they own the idea in perpetuity. In perpetuity. If I move to Pluto, I cannot do a show about a probation officer, even if it's set on Pluto, because they own the idea of Roy as a probation officer.
Host
It's not just that they killed the project. It's that your heart and soul is now tied up in a vault somewhere because they paid you for it. So you can't go back and even do the show with somebody else if you wanted to put, put, put in all this sweat again.
Roy Wood Jr.
Unless they were fully reimbursed dollar for dollar for every single thing that they spent money on to make that original project, including the rewrites for the second. For the second round of the pilot, they will want every dollar back. And even still, they may not give it back. When the time comes and I got the money, I'm gonna go. I'm gonna step to him about it because.
Host
Well, when's that time gonna come, though? Because we were talking just before. I don't want to betray a confidence here, but you said we can go anywhere. Yeah, just before we turned on the microphones, you were talking about. I'm going to say, mumbling something spiritually, cosmically related where you were saying, I really have to consider the signs about doing this all on my own.
Roy Wood Jr.
I think that the more I look at the industry, I think that the next project I do will probably be something that I conjure out of my own head. I don't know what they're going to do with the Daily Show. I don't know what other networks are looking to do with their show. Like, at Midnight doesn't have a host yet. So, you know, my name could be in the half of that. You know, I don't know. But the more I look at this time, where there is, like, industry stillness, you. Your brain goes back to truck stop mode, where you're just sitting, and that's when you start firing off all the good ideas. And I'm going, oh, well, I could do that. Oh, I'll just do that. You start doing the math on it.
Host
Oh, so you. With the time to think for a moment, because you don't have to hustle to the next paycheck. You can do it the same way that you did it in college when you said it pays $27,000 if I go into comedy and it pays 19,000 if I do sports writing. It seems I should do comedy.
Roy Wood Jr.
Correct. So if I have an idea that can reach as many people and I have more creative control, then that might be the better play than going and playing in somebody else's sandbox. Now, I don't have anything to put against that yet because those offers haven't come in because of the strike. But I'm also not going to wait till the end of the strike and then start ideating what the alternative is. The alternative may become the permanent. And I'm not afraid of that because what I keep meeting over the last couple of months, months is people that are now in their permanent alternatives. This is your beautiful alt. This was not the brainchild when you first started the journey. And now I don't imagine you would have. Couldn't imagine being anywhere else but doing this.
Host
Well, it's interesting. It's interesting what you were saying spoke to me just because I'd love to say that I had some sort of great foresight about where the industry was going and therefore I had to jump and do my own thing. Thing. But I felt pushed. And that sometimes when you make choices as well, where. Where I couldn't abide sort of a fundamental disrespect of not having control over my own employees or lifelong friends or people that I care about. And. And so it wasn't. I don't think that I. I think I would have stayed in safety. I would have. I would have not been able to make the growth to freedom that was required because it is. I just had this argument the other day with Stephen A. Smith where he didn't like the appraisal that somehow the people who live leave ESPN view themselves as more courageous than he is by staying. And I'm like. But it is more courageous. Like leaving is the hardest thing. Whether you're pushed or not. It's much easier to say in the safety net, the protective governances and the rigidity is of the corporate. You could very easily take the Daily show, have it offered to you and stay there for the next 10 years of safety and they can have control over you. And you would feel like you'd sold your soul. You would feel that way.
Roy Wood Jr.
Yeah, to a degree. But then what you hope is that you're given an iteration of the show that is consistent with what they gave John, consistent with what Trevor created for himself, where you're Given space, space to be in, exist on your creative terms. There's gonna be some trade off and all that. It'll never be as perfect as you rolling solo, but you rolling solo may never be as profitable as you conceding some stuff. But what is it you're conceding? And I think that's the question that nobody can answer yet because of the goddamn strike. So it's. You can't wait on that either. So it's almost being pushed by proxy in a way. I had a. I had an opportunity to sit with Tom Joyner, the radio syndicated black radio legend.
Host
Legend as identifiable in the industry as anyone in the history of the industry.
Roy Wood Jr.
As whatever you think Howard Stern was for radio and his time during terrestrial. Tom Joyner was that for black audiences. And I had an opportunity to spend a little bit of time with him. And that's actually why I'm even in town now. I. I get to sit with him a little bit. I'm trying to fit. There is an oral history of his show that needs to be told. And I'm going to tell it like that. That has nothing to do with my own career goals or whatever, but.
Host
Oh, but it does, though, does it? Not like, just that you'd be able to tell the story of industry handed down in your family. Like the thing that you and your father cared about is Tom Joyner perfected it.
Roy Wood Jr.
Absolutely, absolutely created the concept of so many things that you see now and like the idea of a scripted audio podcast where it's like a fictional story or whatever. Tom Joyner was doing that shit in 1993 on the radio every morning, writing and rehearsing. So I end up at the Rangers. I gotta give a quick shout out to the Texas Rangers. They hosted us for HBCU Black College Day at their ballpark, and they donated $5 of every ticket to the Tom Joyner Foundation. And we ended up there. I got a shout out to Isaiah Yates and brother Casas. I can't remember your first name, which I think is Roberto, but I don't want to be guessing on nobody's names.
Host
That's all right. I just didn't realize we were in the shout out portion of the program.
Roy Wood Jr.
No, not even. I'm not trying to. I'm just. This is all Tom.
Host
I understand these are. I understand that these are people doing a good thing, and I understand you're trying to credit them.
Roy Wood Jr.
And so we're at this game at Ray Casas. So we're at this game.
Host
You weren't gonna stop until you got Raycott.
Roy Wood Jr.
I had to remember because this is the first ever. That was the other thing. It's really dope that they extended their ballpark to black college grads and let us kick it and whatever. And so Tom is there. And so Tom's foundation has raised like millions of dollars to send black kids to college. And we're talking like 40, 50,000 children over the years, like unreal amounts of money. And his syndicated show was so canon in black homes for so long. And we got to talking about it and he talked about how he was scared to do it at first, like didn't even want to do it. Didn't know quite what to do. Then over the course of the years, you're the number one show. You have all of these accolades and you're whooping ass. And it was still people trying to tell him what to do. It was still a trade off. And, you know, the trade off worked for him. But then I think about how little. I think corporate respects talent now. I think corporate, you know, in an unscripted capacity. I think we're past the legends. I think they look at everybody. It's just replaceable.
Host
What a cool story for you to tell. It's because you don't want the history of what the tapestry of what that program was daily for a long time in an industry that now has fallen apart. Right. Because radio, radio is not that.
Roy Wood Jr.
From Chicago to Dallas every day to do two different shows for four years, I think, then birthed that into a syndicated show that entertained millions and raised even more for whatever disease you want to name. He didn't raise money for it. Whatever college you want to name, he didn't wrote a six digit check. Any black college you can name, they all got money from Tom Joyner.
Host
You don't want it lost to history.
Roy Wood Jr.
No. And so, but, but then imagine how much reverence you have for that project and that thing. And then you get to sit with the person. That brainchild, all of it just on instinct. No one told him. He was just like, I think I'd do this and this could work and I do that, then maybe that'll work. And there were people on the other side of the table telling him he shouldn't do it or all right, now that you're doing it, here's the rules to how you can do it. And like this constant battle, like, you always imagine that there is this land within, in corporate interaction where they stop with you. That's the p. As an outsider looking in. I'm just a correspondent So I, you know, I live a very easy life compared to a host of a show, right. But to sit with someone like Tom and have him just walk through all of the different issues, just create creatively to be in this space, to be where you are and look at what you have and what you chosen to say no to. You know, people like you all have been the architects of your own careers based on your own wants. No one's ever told either of you what you were going to do. So when I look at, like, just even this trip to Miami, like, this is just something on some universe pushing me in a way to at least see and consider things of what could be and not having that fear of the light in the tunnel, and I think that's what we have to let go of as people, is that, you know, jumping is always going to be scary, but it's necessary. And if you've done it before, you'll figure out a way to do it again.
Host
Well, what does the most joyful version of it look like to you? Whatever it is, if you're doing your dreams, creating your dreams so that you can have the balance between being a father at home. Home, because you can't want to be doing this. The idea of being inspired enough to create and hustle is admirable and, and probably feed something in you that was in your 20s and you're grateful to be able to make a career this way. But you can't want to be in 50 cities away from your. Your son.
Roy Wood Jr.
Not every year, no. I have three hour specials left of me already know what they're about. I just got write them. And after those three, I'm done. Like, that's. I mean, I'm blessed to be able to tour right now, and it's good material, but it's not the stuff that I'm gonna like. The next three things are more about me. I want to talk about myself. I'm tired of talking about issues, talking about me, talk about my father, talk about my son, talk about fatherhood. You know, just like that's the stuff that I find interesting.
Host
So what's your next growth, though? It's your 40s and finding the voice. You said 33. Your father until 33, your father would have been embarrassed by your mater. And now you are closer to what your father's age was when he was raising you. And you've learned some things about life, comedy, business, fatherhood. You have material that's new, that's fresh.
Roy Wood Jr.
Yeah. And to me, and then I did an episode of Finding your roots and found out like, all of this shit about my lineage. Like, it's like, oh, okay, well, that's the stuff I want to talk about that's interesting to me. Whereas before, when you're a young comic, you're doing the material that you know is going to get you chosen for TV and the material that you know is going to get you rebooked at a venue. And if your lines up with those two sensibilities, fantastic. But when it starts conflicting, you start losing a piece of yourself as you get older until you find an audience that wants you here. Exactly what you're talking about.
Host
But that.
Roy Wood Jr.
And that's why I am.
Host
But that's where you are now in your career. Evolution. Evolution, absolutely. What are you, 44 now?
Roy Wood Jr.
44, yeah.
Host
You've got an audience now that wants to hear Roy. That's correct. And. And that means that is a value to what your library built over the last 20 years, your Tom Joyner library of stuff.
Roy Wood Jr.
Yeah.
Host
People who have gathered around you want to hear what your evolution is going to sound like because you still care about exploring these ways. This in ways that isn't lazy.
Roy Wood Jr.
But you're trying to build something that you've never built before, that your instincts are telling you are the right thing to build, that no one associated with the construction of that project can see and very few have confidence in. And that includes your agents and managers, that includes the network, that includes other people you might need to help you write it. So you really have to have blind faith. And so that's. That's what I'm learning, and that's what I time. That's the muscle that I've been stepping into. Because I haven't had to work the blind faith muscle for a long time. Really didn't have to work it at all because when I started, all I needed was $365. So I wasn't really betting. I was just doing something different for shits and giggles. Because I didn't want to go do an internship at a TV station and run a prompter for some drunk anchor. Like, I didn't want to do that.
Host
You say blind faith, though, but that what it wouldn't be blind faith. You've got 20 years of knowing what your heart follows ends up paying off in happiness. Because it's not the strategy, it's not your ma. It's not your mind that's leading you here. The hustle has gotten you this far, but ultimately you end up following your heart along all these paths. Don't you like you, you don't ignore these signals even if you're feeling them. You're not like, no, never mind. I've got this feeling figured out. I'm going to do it my way. To me, that isn't blind faith. It's faith. It's faith earned through confidence of, you know, you know how hard this has been better than most. And you know, what has, what has worked for you. It seems it shines through in your work, that your work has confidence in it and it's real confidence.
Roy Wood Jr.
Appreciate that, man.
Host
But I don't have it misread, do I?
Roy Wood Jr.
No, no, no. I, it's earned confidence.
Host
Earned confidence.
Roy Wood Jr.
I definitely bust my ass. And so now, but now the, I guess the penalties for being wrong, wrong or greater, like, it's like, it's almost like the first time in a tightrope act where you look down. I've been doing this 20, 25 years and I've just looked down. Oh. Oh, shit. I'm really up here now.
Host
That's how I feel. Yeah, that's how I feel every day. Oh, I am really up here now. Lloywoodjr.com is tour dates, tickets. Again. He is your favorite comedian's favorite correspondent on the Daily Show. Thank you for being with us.
Roy Wood Jr.
Thank you.
Host
I, I appreciate your time and I appreciate, appreciate your work.
Roy Wood Jr.
I appreciate you, man. Thank you for opening your neon home to me, man. I appreciate that.
Host
Expensive, the neon. All your dreams can come true if you just know how much budget to put into the neon.
Ad Read Male
Mike Fuentes, Chris Cody. Tell me your favorite thing to do while watching sports.
Host
Favorite thing to think hard.
Ad Read Male
Now, don't overthink it, but don't underthink it. Think the proper amount.
Host
Easy.
Roy Wood Jr.
Yeah.
Host
Nice cold milk.
Ad Read Male
Oh, me too. Dude, I'm telling you that it's not just drinking it, it's the. You get a can in your hand, I give one to you. We both have one. We do that and then the little.
Roy Wood Jr.
Bubbles start to pop up.
Ad Read Male
Oh, my God, I just got goosebumps. Feel my arm.
Roy Wood Jr.
Goosey.
Ad Read Male
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Ad Read Female
50 years.
Ad Read Male
I know you're 50 years old. You look like you're 31, maybe 32. Aging grace, that iconic golden color, the simple ingredients that hop. Oh, my, I, I, I got goosebumps again. I can't stand it. Don't look at me right now. And here's the kicker, guys. It's just 96 calories, 3.2 carbs per 12 ounces. The original light beer since 1975.
Host
I'm going to open another one.
Ad Read Male
Ah, that sounds still hitting different five decades later. So whatever your game day looks like, remember, Miller Time is always a good time. Miller Light. Great taste. 96 calories. Go to miller light.com beach to find delivery options near you. Or you can pick up some Miller Light pretty much anywhere they sell beer. It's Miller Time. Celebrate responsibly. Miller Brewing Co. Milwaukee, Wisconsin. 96 calories and 3.2 carbs per 12 ounces.
The Dan Le Batard Show with Stugotz — "The Best of SBS: Roy Wood Jr."
South Beach Sessions, November 6, 2025
Guests: Roy Wood Jr.
Location: Elser Hotel, Downtown Miami
This episode of South Beach Sessions centers on a wide-ranging, deeply personal conversation between Dan Le Batard and comedian-journalist Roy Wood Jr. With humor, candor, and insight, Roy reflects on his life's journey—from his early struggles, career pivots, and influences, to the complexities and uncertainties of the modern entertainment industry. The discussion navigates topics such as resilience, the evolution of comedy and journalism, the fragility of success, family legacy, and the pursuit of creative freedom in a changing media landscape.
| Timestamp | Segment | |-----------|------------------------------------------------| | 00:01 | Dan’s intro; admiration for Roy’s journey | | 02:17 | Roy’s college legal trouble; how stand-up began | | 04:05 | Near-miss with sports journalism; inspirations (Stuart Scott, Fred Hickman) | | 06:52 | The realities and dangers of early stand-up road life | | 09:22 | Cheap touring, making ends meet—Golden Corral and truck stops | | 12:38 | The career “light at the end of the tunnel” is just more hustle | | 17:30 | Obstacles for comedians in sports TV (ESPN’s “guardrails”) | | 19:57 | The complexities in taking over The Daily Show; Late Night’s future | | 28:31 | The journalistic weight of The Daily Show compared to Vice, Oliver, etc. | | 42:55 | Roy’s father’s legacy, activism, and absence of joy | | 53:46 | The burden on Trevor Noah as Stewart’s successor; racial and xenophobic headwinds | | 61:20 | Risks in taking on the top job as a black creator/host | | 86:04 | The art of making people think, not just laugh (Gregory, Mooney) | | 90:05 | Birmingham pride and the longing for home | | 106:48 | The personal cost of touring vs. fatherhood; future focus in comedy specials | | 110:23 | On “earned confidence” and the anxiety of mid-career change |
The conversation maintains the signature Le Batard blend of warmth, irreverence, and deep respect. Roy is candid, self-effacing, and funny—his stories glide from unironic humor about life's indignities to sobering wisdom about race, legacy, and ambition. The dialogue feels like a passing of the creative baton, with two industry outsiders musing on what it means to create, survive, and stay true to oneself, even when the world demands you be otherwise.
Episode link: [Check “The Dan Le Batard Show with Stugotz: South Beach Sessions” feed for full audio]
(This summary skips ad reads and focuses solely on the content of the conversation.)