Chapter 1: What inspired Roy Wood Jr. to pursue a career in comedy?
Kings 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 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'd like to work hard, 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 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.
What's weird, man, is, all right, here's ā because I started comedy at 19, which I would argue ā 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 criticism. 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.
But foundationally, when did you decide that you were going to do funny as a living?
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 said. Well, these cases are usually adjudicated at a five-year sentence, but with good behavior, you're a young man with no priors.
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Chapter 2: How did Roy transition from stand-up comedy to The Daily Show?
A business decision.
And every year since then, it has fiscally made more sense to keep doing comedy.
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. Guns pulled on you. Guns pulled on you.
Paid in cocaine one time. It's definitely been called the N-word a couple times from hecklers. 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 a 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 three hundred and seventy five dollars. 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.
I want to hear about the Golden Corral gig. I mean, how bad were the earliest gigs? This wasn't that long ago. It's 20 years ago.
In that 99, 2000 era Southern buffet. No.
Golden Corral was the shit, bro. I like Golden Corral as a restaurant. Look at me. I'm saying playing it as a venue. No, no, no, no. I worked there.
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Chapter 3: What challenges has Roy faced in the entertainment industry?
I could sleep in truck stops. Yeah. I can't believe that career could be that flimsy with someone, not just with your talent, but your bona fides. 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, 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, I don't know, 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.
But 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 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 I'm going to work America to see if it morphs into what?
A Netflix show, because that's what's buying next.
Correct. 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 transitioned 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, et cetera. 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.
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Chapter 4: How does Roy Wood Jr. view the future of late night television?
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 be in the slot every now and then.
Before the revolution at the position. Correct.
Correct. Hey, you can quarterback third downs during blowouts and you can be in the slot when we've been shotgun or something with Heinz Ward or whatever.
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 that up playing in sports instead of just visiting on occasion, because it spurs your curiosities.
I like that. I've always loved sports, man. I'm not good at it. I'm not good at it.
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, 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. Yeah. Yeah.
I think I could have done that. I think I still could. Like I, 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? You know, and that's kind of what I've had fun doing. during this downtime, but 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 of days and relax and try to create that and go, Oh, he'd love guitars in town. I should go over to his studio and say hello, which is essentially what's happening right now. You know? So I'm,
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 got to go out and do something. So the first thing you do is tour where you can.
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Chapter 5: What lessons does Roy share about balancing career and family?
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 creating opportunities for other people to rebound the ball. Politicians, it bounces off of them. But with fan bases, you could tweet right now something about Pick an issue.
I'm not even saying issue. 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 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 criticizing whatever politician represents their party.
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 ā 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.
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 asshole. 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 wacky land because then the fans don't really... They won't accept that.
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.
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Chapter 6: How does Roy incorporate his upbringing into his comedy?
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 would be okay. But it's too much money involved. It's way too much money involved.
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?
I wasn't moved. I was more inspired by Stuart Scott and Fred Hickman than I was my father in the beginning. Cause 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 name, a riot in the sixties. My pops was there.
So a man like that was, 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. 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 going to fuck with me. So let me figure out how to make people laugh.
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Chapter 7: What insights does Roy provide about the current state of the industry?
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 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.
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 OK, who are you and why are you talking about these things?
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.
Race and xenophobia, not just not just race, like every kind of other.
Don't revisionist 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 did. 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? Like that's where my brain.
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 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.
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Chapter 8: What are Roy's thoughts on the impact of social media on comedy?
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.
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 and it's like relationships. Yeah, 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 will mirror what was before COVID. You are mistaken. The creative taste of people are different. The create 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 to those entities, to those stockholders.
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.
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 live TV events that I think people clamor for that are non-sports. I would say the White House Correspondents Dinner, that's still a relevant live thing.
I wanted to ask you about doing that because I feel like if you can do that, you can do just about anything.
Yeah, but the Correspondents 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 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 going to flow.
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