Roy Wood Jr.’s Guide to Hosting Awards Shows (and Roasting Joe Biden)

Summary

Podcast Summary: Pablo Torre Finds Out

Episode: Roy Wood Jr.’s Guide to Hosting Awards Shows (and Roasting Joe Biden)

Host: Pablo Torre
Guest: Roy Wood Jr.
Date: January 19, 2024

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Brief Overview of the Episode’s Main Theme

This episode dives deep into the world of stand-up comedy, specifically examining the unique pressures and strategies involved in hosting high-stakes awards shows and political events. Pablo Torre interviews Roy Wood Jr., celebrated standup comedian and former Daily Show correspondent, about his experiences entertaining some of the world's biggest stars, including award show audiences and even President Joe Biden at the White House Correspondents’ Dinner. The discussion unpacks the craft and mindset required for hosting, the art of delivering roasts without burning bridges, navigating high-pressure gigs, and Roy’s decision to leave The Daily Show.

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Key Discussion Points and Insights

1. Roy’s Experience Hosting Major Events

• Worlds Colliding: Roy has hosted events attended by an unlikely mix of people—from Joe Biden to Will Smith to Bartolo Colón (01:01).
• Language Barrier with Bartolo Colón: Despite not sharing a language, Roy found common ground with Colón through universal gestures and humor (01:51).
• Strategy for Hosting Award Shows: Roy likens it to being an assassin hired for a night—custom-tailoring material for a particular crowd knowing that "your weapon may not work" (05:26). He talks about his pivotal hosting gig at the African American Film Critics Association, highlighting the unique challenges of making high-achieving, serious audiences laugh (06:14).

2. Challenges of Performing for Serious, Star-Studded Audiences

• High Stakes: “It’s like, twice as hard to get Black people to laugh. And three times as hard to get serious Black people to laugh.” — Roy Wood Jr. (06:14)
• Risk and Reward: “Every now and then you get to juggle dynamite.” — Roy Wood Jr. (06:45)
• The Tightrope: Roy discusses calibrating material that is edgy and flattering—“a complimentary insult”—to connect with the room without crossing lines (08:02).

3. Comedy in the Political Arena: The White House Correspondents’ Dinner

• Preparation and Pressures: Roy compares getting the call to host the dinner to Bruce Willis being sent to blow up the asteroid in Armageddon (14:47).
• Immediate Roasts: Roy started his WHCD set by poking fun at Biden’s classified documents and immediately made fun of himself for half the room not knowing him (19:27; 20:44).
• Context Matters: Roy and Pablo debate why audiences react differently to hosts like Ricky Gervais (embraced as an insider) and others like Jo Koy (met with skepticism) (22:53–24:47).

4. Craft and Growth as a Comic

• Bombing and Learning: Roy shares a formative story about bombing at Showtime at the Apollo and learning to relate quickly to tough crowds (17:05–18:55).
• Three Minutes to Connect: “It’s not about being who you want to be. It’s about showing them that you can relate to who they are.” — Roy Wood Jr. (18:55)
• Self-Awareness: Roy’s approach is self-deprecating, starting sets with jokes about his own identity to disarm skeptical audiences (20:44).

5. Inside the Daily Show/Host Search Fallout

• Decision to Leave: Roy describes his choice to leave The Daily Show as pragmatic, wanting to control his own next steps rather than wait for a new host to be selected (28:01–29:35).
• No Bitterness: “If you think you’re owed something, then go get it for yourself instead of getting mad at someone for not giving it to you.” — Roy Wood Jr. (33:56)
• Future Plans: Roy discusses his love of local/state news and plans to create something rooted in connecting with audiences beyond just political commentary (35:02).

6. Relationship with Ronnie Chieng and the Road Comic Life

• Comedic Brotherhood: Ronnie, Roy’s close friend and former office-mate, calls him the “USA Comic Road Dog” (36:07).
• America Through the Lens of Standup: Roy has performed in 49 states, connecting with Americans from every walk of life—a vantage point for understanding the country (37:02).
• Teaching Ronnie About America: Memorable story of taking Ronnie to his first Waffle House (37:36).

7. Alternate Career Paths and ‘Sliding Door’ Moments

• Almost a Baseball Umpire: Roy shares that he considered umpire school as a way to stay around baseball—until practicalities got in the way (39:58).
• Perfect Storm Dreams: At 18, Roy considered working on an Alaskan fishing boat after being inspired by the movie “The Perfect Storm,” but realized Golden Corral offered about the same pay without the risk (43:46).

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Notable Quotes & Memorable Moments (w/ Timestamps)

• “Best hang I’ve had with an athlete in 10 years, Bartolo Colón doesn’t speak a lick of English, I don’t speak a lick of Spanish.” — Roy Wood Jr. (01:01)
• “Every now and then you get to juggle dynamite.” — Roy Wood Jr. (06:45)
• “Performing for movie stars is the most difficult. The award show is their Game 7.” — Recounting Michael Che’s comment, Roy Wood Jr. (08:59)
• “It’s not about being who you want to be. It’s about showing them that you can relate to who they are.” — Roy Wood Jr. (18:55)
• “At the White House Correspondents’ Dinner...it’s like when Bruce Willis gets the call in Armageddon...” — Roy Wood Jr. (14:47)
• “You need a high energy, you need to connect fast. The audience doesn’t know you, and they’re tipsy. So it’s about relating to them on their level.” — Roy Wood Jr. (18:55)
• “Half this room thinks I’m Kenan Thompson. Other half think I’m Louis Armstrong. President Biden thinks I’m the dad from Family Matters.” — Roy Wood Jr. at the WHCD, illustrating disarming self-awareness (20:49)
• “If you think you’re owed something, then go get it for yourself instead of getting mad at someone for not giving it to you.” — Roy Wood Jr. (33:56)
• [Re: Being let go from a radio job] “I didn’t like how, but I understood the why. ... That lesson just never left me.” — Roy Wood Jr. (32:19)

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Important Segments & Timestamps

• 01:01–04:36: Athletes, Bartolo Colón, and universal language of humor
• 05:02–08:38: Hosting awards shows—comedy as "juggling dynamite," establishing a connection
• 08:59–10:15: Stress of performing for high-profile, high-stakes crowds
• 13:55–15:01: Path to the White House Correspondents' Dinner, prepping for the role
• 17:05–18:55: Learning from failure at the Apollo, quick audience connection
• 19:27–21:32: Roasting the President, starting with self-deprecation
• 22:46–24:54: Host-audience dynamics, Gervais vs. Jo Koy comparison
• 25:05–27:17: Roy’s favorite jokes from the WHCD ("Clarence Thomas NFT", school shootings, Lester Holt approval)
• 28:01–33:56: Leaving The Daily Show, career mindset, creating new opportunities
• 36:07–39:09: Life on the road, mentoring Ronnie Chieng, comedy across 49 states
• 39:58–43:46: Almost careers: baseball umpire, Alaskan fishing boat

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Closing Notes

• Roy’s Next Chapter: Roy has already been asked to return as a host for another major awards show. He is taking control of his career trajectory, focusing on connecting with a diversity of audiences, and perhaps building something new that blends comedy and commentary on local and national happenings.
• The Tone: The episode blends Roy’s sharp wit, humility, and analytical approach to comedy, with Pablo Torre’s playful, thoughtful interviewing. The conversation is candid, insightful, and often self-effacing, offering a look not just at comedy, but at ambition, reinvention, and personal resilience.

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This summary covers the major themes and engaging moments of the episode, capturing the original energy and candor of the participants. For listeners and non-listeners alike, it paints a vivid portrait of Roy Wood Jr.’s comedic philosophy and career crossroads.

Transcript

[Pablo Torre]

Welcome to Pablo Torre Finds Out. I am Pablo Torre. And today we're gonna find out what this sound is.

[Brandon]

Happy to be here. Oh, real quick, Mr. President, I think you left some of your classified documents up here.

[Roy Wood Jr.]

You can get the.

[Pablo Torre]

Right after this ad. You're listening to Giraffe Kings. I have been watching you collect a bunch of experiences over the past year that feel very old school because it's you in a room hosting something in front of human beings. And you might be the only person in the history of the planet to have hosted events, functions, dinners attended by Joe Biden, Will Smith, and Bartolo Colon.

[Roy Wood Jr.]

Yes, Bartolo Colon doesn't speak a lick of English. I don't speak a lick of Spanish. Best hang I've had with an athlete in 10 years.

[Pablo Torre]

I want to know everything.

[Roy Wood Jr.]

Hands down, the best hang. Second only to Tori Holt and Marshall Faulk at a cancer benefit that Torrey Holt used to do. I don't know if he still does, but at the time, it was like 07 08, and I was in the room with all of them at that benefit, and that was a good hang. Like, athletes who did not treat you like you were less than them. Athletes who treated you like, oh, you were professional in your field, and you're here. I respect you as well.

[Brandon]

And this is Marshall Falk. He could easily just go, get the.

[Roy Wood Jr.]

Hell out of my face.

[Pablo Torre]

Yeah. Juke you out of the room.

[Roy Wood Jr.]

Bartolo Colon.

[Brandon]

Only person I know who don't speak.

[Roy Wood Jr.]

The language, who comes in the room, speak to everybody.

[Brandon]

Like, just a gentleman and just hello. And I'm trying to, like, think of some Spanish words.

[Pablo Torre]

What do you hit him back with?

[Brandon]

You're the man. I just said you're the man.

[Pablo Torre]

So you should know that communication is a very important thing to Roy Wood Jr. Who was a man that I consider one of the most talented standups in America. But even more than that, Roy is also one of the most analytical standups in America. Another comedian actually once told me that Roy's comedy and show business mind is so good that he gets a call from a comic every two days just asking for advice, which I now understand because Roy himself went from a total outsider to a guy on stage in the spotlight at very fancy black tie awards shows. And on Monday, for instance, you could find him on stage on TV accepting an Emmy with the Daily show and silently mouthing the words, please hire a host. You can see this on YouTube or the DraftKings Network while standing right behind the Daily Show's previous host, Trevor Noah, who was giving his acceptance speech. Trevor Noah, by the way, still does not have a replacement, which is why Roy Wood Jr unilaterally decided to leave the Daily Show a couple months ago. All of which we will discuss in a little bit after a retired pitcher named Bartolo. Big sexy Cologne.

[Brandon]

So we're in Vegas for the All.

[Roy Wood Jr.]

MLB show, and, you know, it's vets there, and, like, this is the awards.

[Pablo Torre]

Show where they proclaim the equivalent of the all NBA team. Like the All Sport All Stars.

[Roy Wood Jr.]

Correct. And they have this thing the night before where they, you know, MLB was just like, hey, you want to watch hockey? We're going to go watch hockey. And I'm not thinking twice about it. It's just, yeah, I want.

[Brandon]

I'll go watch hockey. And in walks Bartolo cologne with Fred McGriff. And Ronald Acuna is up the hall. Like, it's just baseball players at a hockey. And, you know, you're trying not to fan out. But then I'm like, oh, it doesn't matter.

[Roy Wood Jr.]

He don't. He don't speak enough English to understand what I'm saying. And I can't explain it, but, like, just through eye contact and a smile, it's just universal. And we drink, we cheers, and I'm wearing an Expos Jacket. Bartolo pulls up a picture of him when he played with the Expos? And I'm trying to say to him.

[Brandon]

You used to be slim. And then he says in Spanish, but I don't understand it, but I understood it. I go, you used to be slim. He goes, I'm still slim. Who's nailing jokes?

[Roy Wood Jr.]

The coolest athlete I've kicked it with easily in the last decade.

[Pablo Torre]

In your capacity as comedian, you get called to host these things. And in my mind, it's a little like hiring an assassin. It's like, you have one job, one night, and your job is to basically come up with a custom strategy to kill the people in that room.

[Roy Wood Jr.]

Correct. But also, your weapon may not work. Also, you did not load your own weapon. Someone else helped you load the weapon. You know the jokes, the writers. So might work, might not work. To me, of everything that I had an opportunity to host last year, the African American Film Critics association, that gig was probably the most pivotal because it was the first, like, oh, this one's gonna be some. It's gonna be some heavyweights in the room. Ladies and gentlemen, please welcome your host.

[Brandon]

For this evening, one of the and smartest man on the planet, Roy Wood Jr. Clap it up. Clap it up. Y', all, come on.

[Roy Wood Jr.]

It's like, twice as hard to get black people to laugh. And it's three times as hard to get serious black people to laugh. Like, it's. Viola Davis is in the room. And Angela Bassett, Courtney B. Vance, like Danielle Deadweiler, who was there nominated for Emmett Till.

[Pablo Torre]

I was gonna say, like, emancipation is for, like, things to celebrate tonight.

[Brandon]

You played Emmett Till's mama. She's in the room tonight. Oh, here's a juggle. No degree of difficulty high, but it's fun. That's what makes comedy fun, is that.

[Roy Wood Jr.]

Every now and then you get to juggle dynamite.

[Brandon]

Half this room kind of knows me.

[Roy Wood Jr.]

The other half doesn't. So I feel like I get to operate from an advantage because you don't know what to expect from me. I have no precedent, but back to.

[Brandon]

Back black pain is too much. I don't know how the critics do it. I couldn't do Women can't get emancipation back to back. I had to put a little Abbott elementary in between them two. As a chaser. You gotta chase your black pain with some Abbott. You put a little Corinthi Bronze in there, and then you come back to.

[Roy Wood Jr.]

The paint when you're performing at a ceremony that is honoring the best of black cinema for the year. These are all of our prime five star recruits. Five star directors, five star actors. So if you do anything that pisses off one of them, the whole room is against you. Because we're all together. It's us versus you. Because also, I'm not a star of Cinema. I've done two films in 26 years. My granted one was with John Hamm. You know, hey.

[Pablo Torre]

Yes, much respect to confessed Fletch, absolutely.

[Brandon]

But it ain't Emmett Till.

[Roy Wood Jr.]

It ain't the Color Purple. I'm not a star of a hit black sitcom.

[Brandon]

So you know me and you're cool with me, but you don't know me.

[Roy Wood Jr.]

Enough to respect, to have a high enough level of respect for me to give me permission to take a shot at you and your craft. So what's the joke that misses that nerve ending, but also still is edgy enough and fun enough that can try and connect the room. So my strategy, at least for this year, is connect the room. It's a complimentary insult if you will explain, like, in the sense that I'm gonna say something that you could perceive as negative because you're on edge and you're a star and you're an actor and you take yourself way too serious.

[Pablo Torre]

And you wanna win.

[Roy Wood Jr.]

Yeah. And you wanna win, so you're already way too high strung because you just. This is everything.

[Pablo Torre]

All these people on these award shows, man, they're Gollum from Lord of the Rings. It's like they're there to win. They want the. They want their precious.

[Roy Wood Jr.]

Michael Che tweeted recently. And I just have no, it's on Instagram. He don't with Twitter.

[Pablo Torre]

That's right.

[Roy Wood Jr.]

He should not. Michael Che was on Instagram the other day and he said that award shows performing for movie stars is the most difficult. And I agree with this. And he said it's because the award show is their game seven. It's their chance to win a trophy. So they're dead ass serious. So he said, imagine performing for LeBron James in the locker room before Game 7 of the Finals. As stressed as LeBron is, how open to chuckles is he gonna be?

[Pablo Torre]

Did you see the clip of LeBron after that game that they lost recently? The Lakers lost? And he was asked about Ricky Rubio retiring. What do you think about the career.

[Brandon]

That he has had in the. In the NBA?

[Roy Wood Jr.]

I'm not really in the mood to answer that question, but I respect Ricky. Congratulations on a hell of a career. And if I don't seem sincere when you see this video, because we got our ass whooped again. And I apologize. So it was actually bad timing on the interviewer asking me this question. It's not me, Ricky. So congratulations.

[Pablo Torre]

Basically the message was, this is not about Ricky Rubio, but I don't give a F about this and you should not have asked me.

[Roy Wood Jr.]

Yeah, yeah. It's the only thing in their mind. And now Chuckle man will come out.

[Brandon]

Here and make you chuckle before the most stressful evening.

[Roy Wood Jr.]

So the idea of. All right, what's the connector? Look at all the films. I sat and I watched all the films that were getting nominated. And just trying to find what is the thread between the two. And the thing with emancipation and the Woman King. And I knew Viola Davis would be there. I knew, also knew that Gina Prince Bythewood would be there. Who was the director. Both of the movies are outside. The entire film is outside. And just the idea of convincing a black person to do a movie in a swamp outside for weed.

[Brandon]

For the whole film, if for nothing else. Jean Prince Whitewood should get an award solely because she shot a movie in its entirety in Africa outdoors in the summer. And you convinced Viola Davis to do it with you. Like Viola Davis. I don't know if y' all saw Woman King. Viola Davis was only indoors twice. And Then you was at John Boyega's house. And then. And then you took a bath. Those are the only two times I seen the movie. She was only indoors twice. I'm basically accusing Viola Davis of being.

[Roy Wood Jr.]

Musty, which is a bold move, but it's couched in. Wow. You were outside. That was a dedication to the craft. That was amazing. You didn't even get to take a.

[Brandon]

Bath until act two.

[Pablo Torre]

Like, yeah, yeah, yeah, yeah. Reverse engineering instead of just going, give.

[Brandon]

It a father David. She was out there musty. I know you was musty out there in Africa. Then it's. Who the is this guy?

[Pablo Torre]

Right?

[Roy Wood Jr.]

You can get Angela Bassin and Courtney B. Vance to shake your hand. And I feel like you did all right with the black. Black people, because that's also what you want to a degree. You want some degree of. Because a lot of, you know, I swim in a lot of mainstream waters, but a lot of what I do is to try and inspire young black minds. So the people that create the content that does a lot of the inspiring. It's nice to get a chuckle from that community.

[Pablo Torre]

Yeah.

[Roy Wood Jr.]

I don't think there's anything wrong with being loved by a community. I think you have to have that. Because when the rest of the world chews you up and spits you out, all I'll have is black America. So I have to, like, make sure that I'm not disparaging that.

[Pablo Torre]

All communities matter, Roy.

[Roy Wood Jr.]

Yeah, but when those communities don't with you, and you're 65 and you're struggling.

[Pablo Torre]

To get it, hashtag, all communities matter. I don't think you're hearing me.

[Brandon]

Well, tell them to buy a ticket. I got the metrics.

[Roy Wood Jr.]

I can tell you which communities don't rock with me.

[Pablo Torre]

Let's go inside of the room. The community that is the White House. Correspondence Thinner. Because for people who aren't familiar, this is a. This is a distinctly American tradition that begins in 1921. Traditionally, the president of the United States and the vice president are both there, as long as they're not Donald Trump, I guess. But it's also everybody who seems to have a microphone that matters in Washington, D.C. and the companies and organisms that cover the most powerful people in our country politically. And so do you have a sense as to how you got that call and why you got that call? What was the antecedent for why Roy Wood Jr. Was. Was. Was called up to do this?

[Roy Wood Jr.]

So that I got the. The correspondence dinner is in April.

[Pablo Torre]

Yes.

[Roy Wood Jr.]

January. I go to the White House to cover the warriors visit championship visit to.

[Pablo Torre]

The White House with a Daily Show.

[Roy Wood Jr.]

Correct for Daily Show. And I get a chance to talk to Steve Kerr, Steph Traymond.

[Brandon]

What is one rule that you would.

[Roy Wood Jr.]

Have the president change in the NBA?

[Pablo Torre]

One rule.

[Roy Wood Jr.]

No text. That's an easy one for me. No technical files. You can't go. No text. No, you can. You know, I get a call eventually from Tamara Keith, who was the head of the Press Corps association at the time. I think she still is. She just goes, hey, White House Correspondents association, we think you're funny and you.

[Brandon]

Do good on Daily Show. Would you be interested in.

[Roy Wood Jr.]

Like, it's.

[Pablo Torre]

In the most pressurized opportunity for anybody who does political comedy to engage in.

[Roy Wood Jr.]

It's like when Bruce Willis gets the call in Armageddon and she's like, you're the only one that can do this, Harry Stamper. And then I go, if I'm gonna do it, I gotta have a team.

[Pablo Torre]

That's right.

[Roy Wood Jr.]

Get me the best writers.

[Pablo Torre]

You're gonna drill a hole into this asteroid.

[Roy Wood Jr.]

Yeah. And we need you to try and blow it up.

[Pablo Torre]

Roy, the podium is yours. I'm going to be fine with your jokes, but I'm not sure about dark.

[Roy Wood Jr.]

Brandon.

[Pablo Torre]

It'S all yours, pal.

[Roy Wood Jr.]

It is probably the most nerve wracking gig next to Showtime at the Apollo Amateur Night, which I still would rank more difficult than the Correspondent Spinner.

[Pablo Torre]

How old were you when you did that?

[Roy Wood Jr.]

21? 22. The thing about the Apollo Theater that they don't tell you everybody's drunk.

[Brandon]

People are drinking at the. At least in 02 when I did the Apollo, mixed drinks was $4. So people was having a ball and they block shoot the show. So it's a. Like they're drunk at the Correspondence dinner. But it's classy tuxedo drunk. So I'm just.

[Roy Wood Jr.]

I'm one drink too many into drunkenness.

[Pablo Torre]

Yeah.

[Brandon]

Was it the Apollo cats in the third deck?

[Pablo Torre]

Oh, good night for you. The drunker you are, the scarier you are as an audience member.

[Brandon]

For a comedian, yes.

[Roy Wood Jr.]

For an amateur comedian, absolutely.

[Brandon]

For a room full of drunk people. And I have to impress you, I'd rather be in the locker room trying to make LeBron chuckle.

[Roy Wood Jr.]

You shoot all of the music acts first. Most music acts do two performances, so P. Diddy and the family does two songs.

[Brandon]

DMX comes out and does two songs. Then Ja Rule comes out and does two songs. So the first 45 minutes is just.

[Roy Wood Jr.]

Some of the best peak hip hop you've ever seen.

[Pablo Torre]

You're following that?

[Brandon]

Oh, not yet. No. It's. It's all of these Grammy winners just rocking and Busta Rhymes and just killing it.

[Roy Wood Jr.]

Crowd going crazy at this point. We're about two hours, hour and a half, two hours into this audience just drinking. And then Rudy Rush goes. All right, y', all, time for the amateur comedians. You don't stand a chance.

[Brandon]

All right, we're gonna bring out the next contender. He's been dominating for a while. His weight class is getting up. Y' all from Alabama, y'. All. Birmingham, that is. Y' all. Give it up. My man, Roy Woods Jr. What's going on now?

[Roy Wood Jr.]

Let me take that back. There are comedians that I saw that night who, to this day, I have witnessed very few comedians crush as hard as they crushed. My just wasn't on point.

[Brandon]

But y' all just like down south, man. Fellas, you go to the club, you pay for the ladies drinks, right? Yeah, they cheap like that down south. Keep it real. Drinks cost you much. You feeling me, bro?

[Roy Wood Jr.]

It was one of those bombs where I bombed. And then I stayed to watch the other comedians because I've driven. So I've driven from Alabama. I'm sleeping in my car out in Jersey. No, if I suck, that's cool. But let's see what does well, so I can better understand the psychology of this audience.

[Pablo Torre]

Roy, you were the guy, the athlete who loses the game but is standing on the field watching the trophy presentation.

[Roy Wood Jr.]

Yeah, yeah. As Tommy Jonigan calls it after we lost on last comic standing, I'm standing in another person's confetti.

[Brandon]

Oh, man.

[Roy Wood Jr.]

And you never want to stand in another person's confetti, but I did that night because I want. I have to know. I have to know how. Otherwise, how am I getting better?

[Pablo Torre]

Right?

[Roy Wood Jr.]

Right. That's the whole point of getting booed is to get better. Nobody's gonna remember you. They're gonna remember you.

[Pablo Torre]

Like, what did you learn as you were watching other people's confetti rain down upon you?

[Roy Wood Jr.]

You need high energy. You need to connect fast. You only have three minutes. The audience doesn't know you, and they're tipsy. Some are drunk. So it's about relating to them on their level. It's not about being who you want to be. It's about showing them that you can relate to who they are. And that's the quickest way to connect with a room full of strangers. And even with everything else, I hosted same. Same game.

[Pablo Torre]

Right? And so I want to bring us back to the dais where you take over for the President of the United States, and immediately you shake hands with him and you make fun of him. Immediately.

[Roy Wood Jr.]

Have to. I have to.

[Brandon]

Don't give it up for dark. Brandon. Happy to be here. Oh, real quick, Mr. President, I think you left some of your classified documents up here.

[Roy Wood Jr.]

You can get them.

[Brandon]

Don't give them to him. I'll put them in a safe place. He don't know where to keep them. I must.

[Roy Wood Jr.]

At the time, the document stuff was starting to come up, and I didn't have a lot of material about documents in Mar A Lago, and Mike Pence's name had been swirling, and Biden. We're just like, what if just Biden left documents at the podium? What if we just gave him back his documents that he left? Yeah, that could work. Might not work, but in case it doesn't work, let's do it quickly as he's sitting down. So now if it doesn't work, it feels like it wasn't even a joke that I attempted. Yeah, it's a free joke.

[Pablo Torre]

Yeah.

[Roy Wood Jr.]

Because it's still. We're transitioning. We're trans. The transition of power to the microphone. Then you go, hello, how are you doing tonight?

[Pablo Torre]

There Immediately, you live up to the rule that you set out, which is, I'm going to establish who I am for those who are not familiar, and I'm gonna make fun of myself out the gate.

[Roy Wood Jr.]

I know you don't know who I am immediately, so let's address that.

[Brandon]

I'm well aware that not everybody in this room knows who I am, so let's just address the elephant in the room.

[Roy Wood Jr.]

I know what it is.

[Brandon]

Half this room think I'm Kenan Thompson. Other half think I'm Louis Armstrong. President Biden thinks I'm the dad of y'. All. Family Matters.

[Roy Wood Jr.]

I just feel like in so many situations where I've been hosting, I'm operating against an audience where half of them don't know who I am. So you don't know what to expect. It's not like Jimmy Kimmel at the Oscars. You know Jimmy Kimmel. You know what he's about. So Jimmy doesn't have to. He doesn't have to add preamble at the beginning of his set, whereas I felt like this year for just most all of every show, it's just because they're all different. None of these demos were the same either.

[Pablo Torre]

It's so funny to go look at just like a montage of the cutaways to the crowd because I consumed all Your. In, like, the course of two days. And I was like, oh, my God. Like, they just cut away to a baseball player that I can't even identify.

[Roy Wood Jr.]

Yeah.

[Pablo Torre]

And then they cut away to, again, Will Smith.

[Brandon]

And then, oh, there's Kellyanne Conway.

[Pablo Torre]

Kellyanne Conway.

[Roy Wood Jr.]

And so it's a difference between like, one of my sets and maybe, let's just say Ricky Gervais, when he used to host Golden Globes. Ricky Gervais has a huge advantage over most performers that have hosted the Golden Globes and that he is one of that community at a level of prestige, and they already know what he's about. You already know my politics. You know what I do. So Jervis ain't gotta waste no time. He can come in, just out the gate. Jab, jab, jab, jab, jab. Same as Jimmy Kimmel at the Oscars. If Jimmy wants to take a shot at somebody, he can. Cause half of y' all been on my show. So you know what I'm. You know, whether or not I'm serious or being malicious, where if you're just Joe Blow comedian that the audience doesn't know as much, then immediately they're just gonna go, oh, how dare you?

[Brandon]

Could you believe he did?

[Roy Wood Jr.]

Nobody reacted like that with Gervais, but they did with Jocoy.

[Pablo Torre]

Yeah.

[Roy Wood Jr.]

Same event, same. Same stars.

[Brandon]

As you know, we came on after a football doubleheader. The big difference between the Golden Globes and the NFL on the Golden Globes, we have fewer camera shots of Taylor Swift. I swear, there's just more to go to.

[Roy Wood Jr.]

Sorry about that.

[Pablo Torre]

I was gonna ask how you felt watching him go. Go through the experience of working a room that was not with him in the least at the Golden Globes.

[Brandon]

He did the jokes. You do the jokes that you write. And if they laugh, they laugh. If they don't, they don't. You have to stay true to the material.

[Roy Wood Jr.]

You can't call an audible and lash out and attack the audience. But that's also what I'm talking about in the sense of what they gave Jo Koy wasn't fair because you wouldn't have given that to Ricky Gervais. And Ricky Gervais would have went hard at y'. All. Ricky Gervais would have told y'. All. Ricky Gervais would have opened with an Epstein island joke.

[Pablo Torre]

Yes.

[Roy Wood Jr.]

Off the rip. So this idea of getting mad and then calling a comedian. Oh, he was nasty.

[Pablo Torre]

Right. The idea that Taylor Swift taking a drink from her glass was an indictment of the host, to me, is infuriating not because I loved Jo Koy's set, but just because. Why? That's the indictment of the joke, that she didn't like it.

[Brandon]

Okay, don't like the joke. But then to turn around and go, this was a malicious attack on the community.

[Roy Wood Jr.]

No, it wasn't. It was jokes. If the audience has already decided, we don't. Who are you, then? You're already coming in with two strikes out the gate, dawg. So what I've tried to do with some of these sets is get that out of the way. But that costs time, and you could just be doing the jokes. Joe Coy just did the jokes. Fine. I chose. Hey, political people. Don't he be losing documents, all right?

[Brandon]

You don't know who I am, do you?

[Roy Wood Jr.]

Ha ha, ha. Okay, now let's start. Right, but that cost me four minutes.

[Pablo Torre]

Yep, yep, yep.

[Roy Wood Jr.]

So those are jokes that, you know. Nobody remembers those jokes. The same as the Clarence Thomas NFT joke or something like that.

[Brandon]

Billionaire named Harlan Crow is flying Clarence Thomas all over the world on unreported trips. Like an Instagram model taking Clarence.

[Roy Wood Jr.]

To.

[Brandon]

The Maldives and the beaches. And all paid for his mama's house. This billionaire paid for Clarence Thomas mama's house. I gotta give it up to billionaires. Billionaires. Boy, y'. All.

[Roy Wood Jr.]

Y' all are relentless.

[Brandon]

Y' all always come up with something new to buy. Like, just when you think of everything you could buy on earth, billionaire will come up with a new thing. Y' all buy space rockets. You bought Twitter. This man bought a Supreme Court justice. Do you understand how rich you have to be to buy a Supreme Court? A black one on top of the. There's only two in stock, and Harlan Crow owns half the inventory. We can all see Clarence Thomas, but he belongs to billionaire Harlan Crow. And that's what an NFT is.

[Pablo Torre]

That one's my favorite. I wonder if it is also yours favorite. There are some good ones.

[Roy Wood Jr.]

Nah, the school shooting one I like more, only. Only because it wasn't supposed to get a laugh. And it got the groan that we hoped for.

[Brandon]

Drag queens are not at a school to groom your kids. Stop it.

[Pablo Torre]

Like the groan where it was like.

[Roy Wood Jr.]

Why are you worried about trans people in the schools?

[Brandon]

Even if they were, most of them kids gonna get shot at school. It ain't no problem. Don't grown pass legislation. Like, they booze gonna bother me. I'm like. I'm like Mitch McConnell. I ain't got no soul.

[Roy Wood Jr.]

Those kids are just gonna get shot anyway. I felt like I had a Lot of people that had my back that were looking over me, you know. And also Lester Holt. It's always a good feeling when you look out and see Lester Holt.

[Pablo Torre]

Was he, Was he giving it, Was he giving it up?

[Brandon]

He gave me like the Mr. Miyagi smirk, which fester Holt.

[Roy Wood Jr.]

That's like a standing ovation.

[Pablo Torre]

Absolutely.

[Brandon]

He's like.

[Pablo Torre]

That feels. That's got to feel.

[Roy Wood Jr.]

So that is what black man sound I just made. That wasn't me doing an Asian old man.

[Pablo Torre]

Correct? Correct. I can validate.

[Brandon]

I saw you getting ready to pull that clip and post it.

[Pablo Torre]

That week. You had just hosted the Daily Show, I believe.

[Roy Wood Jr.]

Yeah. Guest hosted the whole week and they.

[Pablo Torre]

Praised you for it at the White House correspondence dinner. That was April. And then in October. For people who aren't familiar with your oeuvre, Roy, you decide to do what?

[Roy Wood Jr.]

Leave.

[Narrator]

The day Michelle Roy Wood Jr. Is leaving the Daily show, the comedian and correspondent for the Comedy Central series revealed his plans to depart the show amid its search for a new host in an interview with npr. According to Wood, his decision to leave was based on the demand of the correspondent's role on his schedule and detention, as well as a disinterest in continuing in the position while, quote, waiting for someone else to take the top job following Trevor Noah's departure last year.

[Brandon]

You have to like, figure out other stuff.

[Roy Wood Jr.]

I wasn't mad, like, it wasn't beef.

[Brandon]

It was just, alright, looks like this.

[Roy Wood Jr.]

Figuring out who the host thing is gonna take a while respect. I'm gonna go and figure out other. And if you need a host or something, I'm around, tell them that. But I'm around, but I'm gonna go figure out because that's just being a correspondent man and trying to figure out what's next for yourself. That's a slippery slope, bro. I love the show. I love everybody over there. But let's be real. I cannot figure out how to do what is next while I'm still doing the thing. Because that thing is so mentally consuming. You're gonna get sent out on this, that and the third field piece and all types of stuff. And so trying to ideate what's next. And then you look up in January and you may find out that you were not a part of the next iteration of the Daily Show. Now you have a shorter Runway to figure out what is next for yourself.

[Pablo Torre]

And you really feared, or at least you wanted to take seriously, the fear that maybe the Bruce Willis you guys hire doesn't want me on his drilling team.

[Roy Wood Jr.]

May not be on his team, which.

[Pablo Torre]

Is crazy to me as an outsider. And I think the reaction from many people was A, you guys up by not giving this job to Roy, but B, I'm curious actually how it feels when people tell you that.

[Roy Wood Jr.]

I take it as a compliment just to the work that we put in, you know, But I think that every host that they've had, with the exception of Craig Kilborn, who was first, you know, nobody really understood Jon Stewart as a choice. And there were a lot of people who didn't want Trevor in the building as well. So there's gonna be people who just gonna go with whatever they choose to do next. They're gonna say they should have done xyz when they named Trevor. There was five other names people wanted instead of Trevor. So I would just trust that the people over at Paramount are deciding what they want to do. And I hope that they prove themselves right with whoever they put in the chair. But it didn't like make me go, hell yeah, damn you right.

[Brandon]

I should have been the.

[Roy Wood Jr.]

It's like, I appreciate that. And if anything, it's just validation to me to go and figure out, all right, well, what do I want to do?

[Brandon]

Because there's people who think I should.

[Roy Wood Jr.]

Sit in a chair. Well, that ain't the only chair. I go build my own chair. I can create a. Meet some. Some of this and one of these LEDs.

[Pablo Torre]

Yeah. Roy, would you. For the podcast audience is gesturing around at this psychedelic laser tag studio that I love.

[Brandon]

Yeah.

[Roy Wood Jr.]

When people say that to me, it's. I take it as a sign of appreciation for the work that I put in and meaning that there's still people out there that care what I have to say about stuff. I just have to figure out the most efficient way to go out and do it. So in the meantime, it's tv, it's film, you know, trying to sell scripts in that regard, because I still like doing that as well. That's the other thing. I don't want to just sit and yell all the time about politics. I've enjoyed not being completely plugged into everything.

[Pablo Torre]

Well, let me ask it to you this way because I. I want to get into what you are doing in lieu of this all consuming job corresponding and then potentially host. But just because I want to register this feeling accurately and honestly. How disappointing was it for you to not be given the job after, you know, it was Hassan Minaj who's going to get it and then he had his, which is a longer podcast to get into.

[Roy Wood Jr.]

That's a separate.

[Pablo Torre]

Which I do want to get into, but not right now. And then there is this vacuum, and it doesn't automatically go to you. And the disappointment on that you would describe to an outsider as. As what?

[Roy Wood Jr.]

It wasn't disappointing. It was just more affirming than anything. I did morning radio for about 12 to 14 years while I was doing stand up, let's just say 12 years and some gaps in there. But the second time, I went back to Birmingham, I went back to Birmingham to host the show, and I got fired over Twitter. I found out on Twitter in the morning that I did not have a radio show. That's how the firing went down. And you go through all the gamut of emotions and anger, and, you know, in hindsight, I understand why we. I didn't like how, but I understood the why. And a lot of it boiled down to at the time, I had booked a sitcom. The sitcom won a second season. I was gonna be spending more time in Los Angeles. I was going to be a host that would have one foot out. Now, when you look at the way radio is done now, it's the norm for somebody to not be in town half the time. But in those days, for the type of radio DJ they wanted, they wanted somebody that would be in Birmingham, boots on the ground. I couldn't, so. But in the moment, it hurt, and I was angry. But then you just recognize it's business. It's all business, man. You don't rock with me no more, and that's business. And that lesson just never left me. So, like, you start getting the anger now, you start thinking you deserve. You start thinking you owed. So if you owed something, then go get it for yourself instead of getting mad at somebody for not giving it to you. But what I couldn't do is wait around again to get Twittered again. You know what I mean?

[Pablo Torre]

Yes.

[Roy Wood Jr.]

And so the idea of recognizing you work in corporate America long enough, you know, when you're not gonna get an answer anytime soon. Mm. I say no answer is an answer. I don't really think that's the case with Comedy Central. I think they're legit. Just. What? Hmm. I don't know. This. We could hire this.

[Pablo Torre]

Yeah. Hey, let's punt on fourth down, maybe.

[Brandon]

Hey, couldn't help but notice that Hassan's out the game.

[Roy Wood Jr.]

Am I still in the mix? Well, we're still assessing everything. We love what you do, Roy, but.

[Brandon]

All right, I'm gonna take off. I love y', all, but I'm gonna be over here doing my Own.

[Roy Wood Jr.]

So you can exist in that realm and also be mad at somebody for not choosing. I mean, you get, you, you think about it and then you go, okay, well, what was the show going to be with me? Would they have even wanted that? I might have been walking into a big creative battle anyway.

[Pablo Torre]

Had you dreamed on that, what you would have done.

[Roy Wood Jr.]

A little bit. Not a lot because I didn't know what the budget, I didn't know what kind of budget they would be giving me. I know it's not going to be 2015. Trevor Noah, budget. The two things I know I love, and this is just wherever I ideate next. I know I enjoy talking to strangers and I love local and state news. I think a lot of what happens in this country is just local and state. And that news connects more to the national conversation. The local news, it's the same national story, but it's quicker, it's more condensed. There's a feel good story at the end of 30 minutes about some dog eating a cupcake. And then Wheel of Fortune comes on. So I spend more time now watching local news from just random cities across the country on YouTube. And that's what I do.

[Pablo Torre]

I was texting your former office mate at the Daily Show, Ronnie Chang.

[Roy Wood Jr.]

Ah, that's the chain man friend of the show who still lobbies for me to come back to Daily show, by the way. He texts me like once a month.

[Pablo Torre]

Ronnie Jang texted me two things. He texts me terribly misspelled sports takes. And he texts me things lately about why he loves you. Because I asked him like, and it just hasn't stopped. I'm like scrolling through this right now. It's paragraphs, dude. And, and one of the things, just to distill it, one of the things he, he sort of circles in his scouting report of you is that you were his guide to America and that, and that you, as his guide to America, he realizes now were the perfect guide because he calls you and this is just his, his, his terminology. USA Comic Road Dog has done comedy in every state except maybe Alaska. Ask him about his journey around America.

[Roy Wood Jr.]

49 states.

[Pablo Torre]

And that's what you have been doing also this year since leaving the Daily.

[Roy Wood Jr.]

Show to the basics.

[Pablo Torre]

You're on the road, seeing the country, seeing these people in these local news stories that you're watching as well remotely on YouTube.

[Roy Wood Jr.]

Well, because it's easy to get an idea of what you think America is if you've never met and interacted with these folks. But, you know, before I did Daily show, I was 15 years on the road, like just every year, 50,000 miles on my car just driving.

[Pablo Torre]

And the fast food. Also Ronnie mentions, yeah, Ronnie won't eat any of it.

[Roy Wood Jr.]

I took him to his first Waffle House one time in Ohio during the RNC in 2016. We took a 35 minute Uber ride to Akron.

[Pablo Torre]

What a mad lib he had.

[Brandon]

Never experienced it.

[Pablo Torre]

I'm like, you got to.

[Roy Wood Jr.]

He was not impressed. And you know, Ronnie, like, eats healthy. There's nothing healthy at Waffle House. I'm like trying to get him to try cheese grits. And I didn't know at the time. He's like trying to like, get in shape for crazy rich Asians.

[Pablo Torre]

I know. Marvel movie. Bring him to a Waffle House.

[Brandon]

All American.

[Roy Wood Jr.]

Ronnie, Ronnie. I love, man. Ronnie, like, that was like a. I don't know, closest thing to like an office brother. Like, he talk about work wives.

[Pablo Torre]

The. The show that is just you two guys in a room together teaching each other about.

[Roy Wood Jr.]

Almost happened. So Ronnie and I shared an office with the only two correspondents who shared an office. So our conversations, we had a TV between our desk. And so one of my. One of the things I do when I'm just writing in general every day, I try to watch 30 minutes of a channel that I've never watched and never. Or watch 30 minutes of a program. Just what are other people into? Let me just watch it and it may pop an opinion in my head. It may. Whatever. And so we just watch random channels. And some days Ronnie would have a question and that would go off into an hour long conversation. Sometimes an art. Like when people talk about the early days of Kornheiser and Wilbon and how they would argue at the Washington Post. That's Ronnie and I in the back hallways of the. You just hear two see a black and an Asian. Just.

[Brandon]

But why would you do that? That doesn't make sense. It does make sense. In baseball. It's an unwritten rule. Unwritten rules are stupid. Unwritten rules are what keep the game in order, then write them as rules. You can't write them as rules. You can't legislate hitting somebody, but you can hit somebody as legislate.

[Roy Wood Jr.]

So duck season, rabbit season, type of.

[Pablo Torre]

Totally.

[Roy Wood Jr.]

Ronnie was the first person I told. I had a kid on the way. Ronnie, Ronnie. Like when I say, like, we're close, like, yeah, hey, man, I want to be a dad. Good luck with that.

[Pablo Torre]

Ronnie told me another detail about you, which is my favorite detail about you officially now, which is that. And I get his language Right here. He almost became a baseball umpire.

[Brandon]

Yeah.

[Pablo Torre]

What the.

[Roy Wood Jr.]

The Harry Wendelstedt School of Umpiring in Florida.

[Pablo Torre]

Okay, how real, how serious was this ambition?

[Roy Wood Jr.]

I didn't know that you had to house yourself. I thought it was just pay for the school and just, you know, you go or whatever. Like it's like a couple of weekends. It is not a couple of weekends. It's months of that and I would have had to come off the road to do it and I thought it was like a couple of weeks or something like that and I could couch surf with some other comedians.

[Pablo Torre]

When, when was this?

[Roy Wood Jr.]

This is early twenties. Like once you realize you're never gonna play baseball and you're trying to figure out a way to still be around the sport. And then I started doing the metrics of the money of it all and it was like I was already in the middle of one broke ass struggle which is open mic comedian around the south. And then the idea of paying thousands of dollars to learn professional umpiring knowing that your first gig is still gonna be some high school games. And then you get college after a while, then you get mindless, like do you understand how long it's going to take you? And then, then I just started watching baseball and I noticed like there's really. And I could be wrong but just in first glance there didn't seem to be many umpire, professional major league umpires under the age of 40. So I'm like, and I'm like 20, 21. I'm like, she told me for 20 years I just got to do high school games for $70. And also these games are going to restrict my travel so I'm not going to be able to do it. So you know what, I'm just going to pass on the Harry Wendelstead school event. But it was in the back of a Beckett baseball card monthly. And I remember, never forget what a.

[Pablo Torre]

Publication to find an alternate timeline inside of it.

[Roy Wood Jr.]

Yeah, every, every, every month they would send out a magazine.

[Pablo Torre]

Jim Tome rookie cards worth also. Wait a minute.

[Roy Wood Jr.]

Yes.

[Pablo Torre]

Why were you drawn to the job of umpire? Because I imagine an umpire has power. Certainly they're in the game, but also they have some stage time.

[Roy Wood Jr.]

It is drunk with absolute power. Yeah, it is, it is. I don't know, I just never, I just, I just always. Even now, still trying to figure out a way just to be around the sport of baseball. And so you know, now you know, I'm trying to be a booster for my high school team and do stuff for the city they got the throwback game in Birmingham this year in June. So we're trying to organize some stuff with MLB about that, but I don't know. I just saw it as an easy way, what I thought, to make money on the road by traveling as an umpire. So my big plan was like, in those days, you could get booked in the city for like two weeks straight as an emcee, like certain comedy clubs. And comedy clubs were like proper five, six day venues.

[Brandon]

So you'd be in town for two weeks.

[Roy Wood Jr.]

I worked day jobs when I was on the road. I'm like, well, umpiring. You make a little more and it's less time. You know, 50 bucks a game. The game is only three hours and minimum wage was like five and a quarter. I'm like, yeah. And then I get there and then I can just umpire from 4:00 clock to 7. The show's at 8.

[Pablo Torre]

You were gonna do both. That was your goal.

[Brandon]

But I was already doing a job.

[Roy Wood Jr.]

I was already working 8 to 5 in factories. And, like, I was working just regular day labor, like straight up. Like, sometimes I would go to daily work, daily pay places, improper paperwork, and other days I'm just in front of.

[Brandon]

The Home Depot like everybody else.

[Roy Wood Jr.]

You need yard today. Cool.

[Brandon]

And then I would go do jokes that night. So I'm already working. So, yeah, umpiring school.

[Roy Wood Jr.]

The only thing wilder than that was in college when I thought I was gonna work on a fishing boat in Alaska, because George Clooney, Perfect Storm, it came out and I was like, that's like, seems like a cool job.

[Pablo Torre]

We're looking at 40 to 50 foot waves, gale force winds. It's a real bad one right in our path.

[Roy Wood Jr.]

It was like $3,000 for the month. And I'd never seen that type of money. $3,000 a month at 18.

[Pablo Torre]

I just want to point out that you are simultaneously one of the most deliberate thinkers about your craft that I've ever met. And also seemingly one of the most easily influenced people that I have ever had sit at this stage.

[Roy Wood Jr.]

It was.

[Pablo Torre]

It was, to be fair, I saw the perfect storm.

[Brandon]

Yeah.

[Roy Wood Jr.]

I was like, that ain't a job. That's some man. Like just on the ocean and it's dangerous.

[Brandon]

It's badass.

[Roy Wood Jr.]

I was like, yeah, I'll do 3,000amonth. And then once you do the math of really laying out 40 hours a week, I was like, golden Corral pays about the same. So I ended up at Golden Corral instead of going to Alaska. It should have gone, should have gone. $3,000 a month, man.

[Brandon]

At 18 years old.

[Roy Wood Jr.]

That's bread. Those were desperate times, man. You try and make money, do whatever.

[Pablo Torre]

You can, whatever you do next to make Money. Roy Wood Jr. I am. I am excited to see it.

[Roy Wood Jr.]

I appreciate it, man. Appreciate it.

[Pablo Torre]

Thank you for letting me stand in a little bit of your confetti today.

[Roy Wood Jr.]

This is probably as good a time as any to mention that one of those award shows from earlier has already called me about coming back next year. I can't say which one because it's not public yet, but I'm gonna go back.

[Pablo Torre]

So just when you thought you were out.

[Roy Wood Jr.]

Yep. And that's. Watch that be the one I bomb should have left on a high. What do I do? Go back again. Armageddon too.

[Pablo Torre]

Go. But speaking of a whole squad of people who are dedicated to helping the host, not Bob, I should point out that Pablo Torre finds out is produced by Michael Antonucci, Ryan Cortez, Sam Dawig, Juan Galindo, Patrick Kim, Neely Loman, Rachel Miller, Howard, Ethan Schreier, Carl Scott, Matt Sullivan, Chris Tominiello and Juliet Warren. Our studio engineering is by RG Systems. Our post production is by NGW Post. And our theme song, as always, is by John Bravo. And yeah, we will see you next week.