Roy Wood Jr. on The Daily Show and the Future of Comedy - The Assignment with Audie Cornish - Podcast on CNN Audio

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The Assignment with Audie Cornish

Every Monday on The Assignment, host Audie Cornish explores the animating forces of American politics. It’s not about the horserace, it’s about the larger cultural ideas driving the American electorate. Audie draws on the deep well of CNN reporters, editors, and contributors to examine topics like the nuances of building electoral coalitions, and the role the media plays in modern elections.  Every Thursday, Audie pulls listeners out of their digital echo chambers to hear from the people whose lives intersect with the news cycle, as well as deep conversations with people driving the headlines. From astrology’s modern renaissance to the free speech wars on campus, no topic is off the table.

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Roy Wood Jr. on The Daily Show and the Future of Comedy
The Assignment with Audie Cornish
Feb 1, 2024

Jon Stewart is returning to The Daily Show, putting the spotlight back on this influential institution of political comedy. Today, Audie talks with a breakout star of the show’s very recent past, comedian Roy Wood Jr. He pulls back the curtain on his time at The Daily Show, schools us on the economics of entertainment for a creative, ambitious, working parent, and dives into whether comedians should fudge facts to get to a higher truth. 

Find out if Roy is on tour near you. 

Episode Transcript
Audie Cornish
00:00:00
I remember the first time I was in a room with Roy Wood Jr. I mean, not just me, everyone. It was April 29th, 2023, when he headlined the White House Correspondents Dinner, which basically meant he got to roast a sitting president on national television.
Roy Wood Jr.
00:00:15
You've had quite a few scandals, you know, and we know about the documents, we know about the laptops. But there's been no scandal more damaging than the scandal of: Is Joe Biden awake? Say what you want about our president. But when he wake up from that nap. Work gets done. You might doze off, but the infrastructure bill. Student loan forgiveness. Did we free Brittney Griner? Free Brittney Griner!
Audie Cornish
00:00:47
So I was sitting at the CNN table trying to avoid becoming an internet meme with an ill timed smirk. But it was, by all accounts, a great night for Roy Wood Jr. And that only increased the chatter that he would replace Trevor Noah as the new full time host of The Daily Show. The Comedy Central program had basically been holding public auditions, with a roster of all star comedians taking turns behind the desk. Chelsea Handler, Hasan Minaj and Roy, who had served as a correspondent for the show for eight years. But this all went down before the historic writers strike, and by the time the lights came back up, a lot had happened. Minaj was taken out of the race by a New Yorker exposé, and Roy Wood Jr stunned the comedy world by dropping out of the race without an obvious destination. So when we sat down in New York for an interview, it felt like there were a lot of unanswered questions. Well, until this.
Dana Bash
00:01:46
Some breaking news from the world of media and politics. Jon Stewart is coming back to The Daily Show as executive producer and part time host. CNN's Oliver Darcy has the story from New York. Oliver.
Oliver Darcy
00:01:58
Yet again, this is huge news in the entertainment...
Audie Cornish
00:02:00
So today I want to bring you that conversation because Roy Wood Jr is so much more than his time on The Daily Show, what he's learned about the economics of comedy, his family legacy of storytelling, and how he's thinking about his future. This is The Assignment. I'm Audie Cornish. So those public auditions I mentioned each week, a new comedian, including Roy, tried their best to prove that they could connect with a very devoted audience. Roy says they were always, in a sense, at a disadvantage.
Roy Wood Jr.
00:02:40
The best political comedy comes with stakes, and you can only hit those stakes if there's a relationship. It's no different than the Correspondent's Dinner, the viewer has to know the host and see the host repeatedly and get a relationship and get a rhythm and then understand where you're coming from. And then you can do more daring stuff. You know, if they're going to use the news team, that's going to be great for the show in an election year because everybody knows them. Everybody's familiar with them. And, you know, with guest hosts, it's like it's it's literally a different quarterback every week. And they may have a different comedic flavor. And it's it's great to play around with that some. But if comedy and news satire flows through the host, you know, you want you want as many a familiar face or as many familiar faces there as possible. But, you know, I...
Audie Cornish
00:03:49
I mean, you were so frustrated by this process. You exited, right? I mean, this was one of the reasons why you you were like, look, you guys are taking your time deciding, and maybe I shouldn't have to wait around for that.
Roy Wood Jr.
00:04:02
Yeah, it wasn't frustration as much as it was fear. It was more fear, like for my own career. Like, I don't know what you are going to do. I don't know how. I don't know how you're going to make moves. So let me start thinking about what's next now, while I still have a little bit of time and the strike was about to end.
Audie Cornish
00:04:25
The writers strike.
00:04:26
Yeah, this is top of October '23.
Audie Cornish
00:04:28
You didn't say what you were afraid of, though.
Roy Wood Jr.
00:04:30
I was afraid of being a man without a country. I was afraid of them hiring a new host that doesn't want me. I'm afraid of not being in the plans. If you don't know what the plans are and what you're looking at doing, I have to hedge bets on. Okay, well, let me take the time now, before January and before February, to start looking at other things and exploring other things. And I just creatively, I just didn't think there was a way to do that and honor the position of correspondent appropriately and do the job right. So, you know, am I in the mix to host? I don't know.
Audie Cornish
00:05:05
Do you want to be?
Roy Wood Jr.
00:05:06
Yeah. I mean, I've always I've said if they call me and I hear you come back a host. Yeah that would be a conversation. I would consider that. But in the meantime we're talking about the job of correspondent. We're talking about correspondent. We're talking about what's the plan. And as if as they were still figuring that out. Let's talk. Okay. Well, let me go figure out some of the things, too.
Audie Cornish
00:05:23
From the outside...
Roy Wood Jr.
00:05:24
So everybody figuring out stuff.
Audie Cornish
00:05:25
...a person would think, you know he just did the White House Correspondents Dinner like everyone's he did such a great job when he was filling in like it's hard to picture from the outside you feeling fear about where you were because it felt like last year was a very good year for Roy Wood Jr.
Roy Wood Jr.
00:05:43
Okay. But then if that's true then that means there's opportunities other than the Daily Show out there for me. So rather than wait around here and put myself in a position where I'm looking up at some point in 2024 and not knowing what like entertainment is musical chairs. And if it's one thing you know that's true, or that I believe to be true about entertainment right now, companies are making there's going to be less television in the next couple of years. Fewer shows, fewer networks, fewer opportunities.
Audie Cornish
00:06:16
Right.
Roy Wood Jr.
00:06:17
To exist as an actor.
Audie Cornish
00:06:18
Because of the smaller audience. So The Daily Show is a good example, like the audience that it had 20 years ago. Even at its height under Trevor Noah, the numbers, raw numbers were not the same.
Roy Wood Jr.
00:06:29
Correct.
00:06:29
Because the cable audience or the news, the ...I'm like cable news, because the TV audience is shrinking for anything except live football, I think.
Roy Wood Jr.
00:06:37
Yeah, and award shows. So now you have all of these cable companies and streamers merging because they're starting to lose money, right? A strike hit actor strike hit. Both, you know, both unions won for however you define a win. Either way they got to pay more money — the studios, have to pay more money to writers and actors. They're already figuring out workarounds around some of the concessions that we won in the in the strike.
Audie Cornish
00:07:13
You're seeing a lot of outside changes in the media landscape in particular. I would also argue probably comedy.
Roy Wood Jr.
00:07:22
Hell yeah.
Audie Cornish
00:07:23
That make that job, which once was kind of considered like a pinnacle type job, a job where you've made it, makes that job look really different.
Roy Wood Jr.
00:07:32
'And you don't know what you're going into. So now imagine if you're at a job and you're not sure what the plan is for you to host or not, or to continue as a correspondent next year, depending on what the new creative iteration is of the show. You don't know what that is, and you know that your alternative is scripted film and television, right? Or creating your own non-scripted show? Well, the best opportunity to create your own non-scripted show is at the end of a strike after you killed at a Correspondents Dinner. So that's option one. Option two is to try and do something scripted or make films, which they're also making less of. The studios don't have money the way they did anymore. They're not going to be throwing money at a bunch of different TV shows. They don't make pilots the way they do anymore. You're not even going to have a cast of a bunch of people anymore, like 8 or 9 people in a show. No, writing's on the wall. A year ago, Bob Hearts Abishola had, I think, seven series regulars. They cut the show to two series regulars and then made everybody else recurring, and that's one of the tricks.
Audie Cornish
00:08:35
So now that's where you get one of those shows where it's like two people in an apartment and other people who stop by.
Roy Wood Jr.
00:08:40
Correct. And so and for the, for people don't know the difference like a series regulars, someone that's in every single episode or recurring is someone who comes ...like like Newman in Seinfeld, or Bruh Man from the fifth floor in Martin. That's just someone who's in three, four episodes a year who you don't see all the time, but they're in the world, you know. So if you are, if there are less, if you're making less television and the television you are making you're making for cheaper than that. That changes type of idea that somebody will buy. Buying season is January to April. It's not necessarily a formal pilot season anymore, but let's just assume that Q1 of 2024 is when things are going to get purchased.
Audie Cornish
00:09:28
So all your studios, your streamers, all those people who are doing, you know, the festival circuit, etc. they're also on the lookout for new TV shows. And this is what you're calling buying season.
Roy Wood Jr.
00:09:39
Yes. Now try and ideate that while also following people around the campaign trail in Q4 for The Daily Show. And tell me how much time you still have left creatively to create a decent idea as a parachute. If things don't go the way you hope that they go with the show that you love, which one are you going to bet on?
Audie Cornish
00:09:58
I'm Audie Cornish talking with Roy Wood Jr. We'll be back after this. I'm talking with Roy Wood Jr. He's a producer, actor, writer and comedian. You're coming of age in your career at an interesting time in the industry that at one point the goal was get on The Tonight Show or whatever, get a sitcom. Then it was again, that late night circuit maybe.
Roy Wood Jr.
00:10:28
And then it was get on MySpace, then it was, oh, you got to get a Twitter and and YouTube and you know, like it's.
Audie Cornish
00:10:38
And now there's, there's also a lot of competition for making a comedy special. Right. Like a lot sometimes when I hear controversies bubble up in the comedy space, it's because of somebody's special. You're trying to get attention for it, trying to get money for it, trying to get it bought. That's the other kind of finite resource, it seems.
Roy Wood Jr.
00:10:58
Yeah, but then there's also more eyeballs on TikTok than any two streamers you could combine for the most part. So is an hour special still the lick? Might not be might be better off taking your hour jokes, chopping that thing down into 90 second chunks and putting it out on TikTok and riding the algorithm to sell out crowds. There's comedians that I can name who were selling out stadiums, selling out theaters before they had an hour special. That's a whole turn on its head. 20 years ago, you do good on Letterman. You do good on Leno. A network like shit, they give you 30 minutes or they give you an hour. So many people see your hour. Now you can sell a theater. Yeah. There's also an option within all of this, as the economics and creative get on a crash course, the self producing of so many other things, you might not even need any of these people. That's an option too. But if that if that's to be considered...
Audie Cornish
00:11:55
Produce your own special. Book your own tours, etc..
Roy Wood Jr.
00:11:58
Yes. Love them or hate them, there's a recipe that Joe Rogan set in motion that Marc Maron set in motion, that a lot of other comedians have started to finally figure out, and how to crack that code. You know, the Bert Kreischers of the world, the Tom Seguras of the world, the 85 Souths of the world.
Audie Cornish
00:12:21
I want to ask you about Hasan Minhaj.
Roy Wood Jr.
00:12:24
Okay.
Audie Cornish
00:12:25
Because he he's someone just to get people caught up. He was the host of the Patriot Act. He also was one of the sort of prospects for filling in of The Daily Show next. And he was accused of not being accurate with a handful of his stories from his stand up act. One was the idea that he was rejected by his prime date's family due to racism. One was about FBI informants harassing Muslim communities, after 9/11, and another was a story about receiving a letter with white powder, that he said the letter was threatening to his family. So each of the stories was fundamentally true. But as he has said, this sort of some of the details were fudged in order to make it work for stand up.
Roy Wood Jr.
00:13:10
Correct.
Audie Cornish
00:13:11
This is someone who uses their comedy to, they say, tell emotional truths or essential truths about our culture in society.
Roy Wood Jr.
00:13:21
To inspire and to make people feel about an issue. Right.
Audie Cornish
00:13:27
Did he fail in that responsibility.
Roy Wood Jr.
00:13:30
In the performance capacity? To some, he did. I felt like at the core of what he did, it's not that different from what a lot of other comics do for material that's less impactful, you know, in terms.
Audie Cornish
00:13:43
But isn't that the problem?
Roy Wood Jr.
00:13:44
Yeah.
Audie Cornish
00:13:45
Well like it is impactful, right.
Roy Wood Jr.
00:13:47
Like if you take the Chappelle — and this is a terrible analogy — but it's the Chappelle. It's the Chappelle. I saw a baby on the corner smoking weed like an infant. It's a joke that Chappelle did years ago.
Audie Cornish
00:14:02
I remember it.
Roy Wood Jr.
00:14:04
He's just painting the picture of the ghetto. There's no baby actually smoking weed, XYZ. I think that if Hasan chose to use, if he chose to change up some of the story, to invoke extra emotion, to get people to pay attention to it, is it the wrong tool? It's not what I would have done, but at the source material is the racism still there? Is xenophobia still there, are all the things that he's trying to shine a light on. Do they actually exist? And to me, they still do, like...
Audie Cornish
00:14:37
But you are so much about fact checking. Like, I feel like one of the interesting things about your joke writing is like you bring a writers, almost a journalist approach.
Roy Wood Jr.
00:14:48
That's my broadcast degree. Like I'm thinking I still write my material out AP Stylebook.
00:14:55
I'm sorry. What?
00:15:00
When you turn in your hour special to Comedy Central, you have to send a transcript of it. Verbatim for legal to look at. Just to make sure there's nothing crazy in there for them to get sued. And when I type that out, it's still AP Stylebook style.
Audie Cornish
00:15:18
Okay having worked at the AP that's amazing. But also that is the to me, I guess what I'm getting at is for those of us who work in this, in this area of communications, who are black and brown, who are from marginalized communities, who do embrace some sense of mission in doing it, I feel like we have extra scrutiny, like the facts matter. Yeah, like you can't get away with the essential truth. And there's something about blurring that line. As soon as comedians got behind a desk and started accepting their Emmys and awards for this stuff. I feel like the bar is different.
Roy Wood Jr.
00:15:57
Then I think the issue I think the issue not just with Hasan, but just like with comedians as a whole, is when is it comedian entertainment hat and then when is it behind the desk hat? And I think when you're behind the desk, it's two different occupations. But in the eyes of the public, I think it means that they recognize that people see us as one contiguous entity....
00:16:16
They do.
00:16:17
...throughout all different mediums. But is that fair to the comedian? To where now he can't because Hasan did what he did.
Audie Cornish
00:16:23
No one asked you guys to pull up a desk.
Roy Wood Jr.
00:16:27
Okay. But then if I'm going to go over here and do truth thing, then I can only be truth forever, verbatim down because over here I am truth man. But when I leave the Patriot Act studio and I go on stage, what freedoms do I get within the medium of comedy where for decades people have all bent truths a little bit for the sake of emotional stuff, not with the same stakes as terrorism and watch lists and Patriot Act detaining people in cages.
00:17:00
And maybe that's where we differ. I see the stakes.
Roy Wood Jr.
00:17:03
So then, which comedians are beholden to verbatims versus the one which which comedians should we hold to the factual verbatim versus the ones we don't?
Audie Cornish
00:17:15
I guess I don't mind my I don't mind the work being done and the accolades being accepted along with the responsibility. Because as journalists credibility is all we have. I'm one bad story away from almost never working again.
Roy Wood Jr.
00:17:34
Correct.
Audie Cornish
00:17:34
One bad story for me doesn't lead to a tour named after me making bad stories. You know, like there's no after. But I feel like comedians have dallied in this space, and now there's a little bit of like, whoa, whoa, wait a second. It's just jokes.
Roy Wood Jr.
00:17:49
But that goes back to what I was talking about, because now it's it's the consumer, the comedy deciding the content and stakes of the material and not the comedian. And I don't think every comedian...
Audie Cornish
00:17:59
Say that again.
Roy Wood Jr.
00:18:01
The consumer of the product is dictating the stakes and the impactfulness of the material, not the comedian. The comedian has never got on... Most comedians I know, they're not getting on stage with the I'm right, you're wrong with their chest out. They are more likely to do that at a desk than they are on stage, like it would be... this isn't a great analogy, but it would be like watching Bill Maher's television show and Bill Maher's stand up. To me Bill Maher's television show was much more braggadocious. It's much more chesty in terms of what he portrays his beliefs to be, whereas his standup, it's a little more lighter. He might hint at whatever.
Audie Cornish
00:18:42
Yeah, but I would argue that the more punchy version is the one that lives in our minds culturally.
Roy Wood Jr.
00:18:49
Okay, so then I can only do I can only perform in that style because the audience is not chosen to receive it.
Audie Cornish
00:18:54
I think what I'm doing is talking to you about this very interesting moment for The Daily Show and the shows that were like it, some of which have faltered. Right? That the parody of news.
Roy Wood Jr.
00:19:09
Correct.
Audie Cornish
00:19:10
Is it feels like this moment feels different. And as someone who, by all accounts, kind of nailed the white House Correspondents Dinner thing, like, you found a way to make those jokes, right?
Roy Wood Jr.
00:19:24
Yeah. I mean, I like that I find fun.
Audie Cornish
00:19:28
But you did it without compromising truth truths as well as your emotional truths.
Roy Wood Jr.
00:19:36
Understood. I, I think that what he did. And I understand why. What happened with Hasan piss pissed some people off. Especially Daily Show, especially Daily Show viewers, because for them there is no difference between desk joke and stage joke. But there is. And so for them, if it's if you're Comedy Central, half these corporations ain't going to bat for talent anyway. But was he ever not factual at Patriot Act? And to me, that's the question. Because in my brain as a as a comedian. Desk Hasan nailed it. Did everything he was supposed to do over the Patriot Act. Won a couple of Emmys. All right. Can you handle this desk, too? I would say yes, but if you question Comedy Hasan, then you're going to automatically question Daily Show Hasan. But at no point did anybody go back and vet anything that he said at the Patriot Act. Or if they did, it all checked out. So none of those stories ever came up. So if we're not going to like when a prosecutor comes up dirty and you got to go back and look at all the cases.
Audie Cornish
00:20:52
Yeah. What's it like to be in this moment? You look it looks a little heavy.
Roy Wood Jr.
00:20:58
It's exciting.
Audie Cornish
00:20:59
It is.
Roy Wood Jr.
00:21:00
It's exciting.
Audie Cornish
00:21:01
All right, give it to me.
Roy Wood Jr.
00:21:02
Is this no different than open mic? And if anything, I'm now armed with the knowledge of knowing that the industry is going to change. So now the biggest mistake you make as a comedian is that you inherit the goals of your predecessors is because you don't know any better. You come into the game as a, as an open mic'er and you open for some headliner who's trying to get on Leno. Man, I tell you, man, I got to get there. I heard there's a scout coming next week to Atlanta. You guys got to get over to Atlanta. There's going to be a scout from Leno, and then I get on Leno. So then that's for the next ten years. That's what you think you need to be doing. Meanwhile, as some other comic you ignoring in the corner, uploading videos to YouTube and you going, that's stupid, why are you doing that? You need to be getting on.... Oh my God, he's selling out theaters. So. It's exciting in the sense of I know how to do the job and now I know how to read the trend.
Audie Cornish
00:22:18
But it does help me reframe your decision around The Daily Show. Like this thing that you're saying about not inheriting the goals of the people that came before you.
Roy Wood Jr.
00:22:28
The chair might not be for me.
Audie Cornish
00:22:29
Yeah, you can only let go of something if you really internalize that idea.
Roy Wood Jr.
00:22:34
Yeah, I'm not going to sit here and beg God, let me host the show or anything. It might not be for me, and it also might not be where the game's going. Let me look and assess. Now, if y'all call me and go, hey, man, you thing about hosting? Okay. Sit down. That's all on the table. But for now, this industry does not look like how it looked in 2015. I need to sit still in and ideate. And I know that I creatively, I'm at my best when I'm not doing a lot. I'm only touring. You look at my calendar, my touring calendar right now, I'm only going out three days a month for the most part, maybe four. I'm not doing a lot. I'm not going anywhere. I'm. I'm sitting and...
Audie Cornish
00:23:19
Being still.
Roy Wood Jr.
00:23:20
And just ideating and let my son trash me at chess.
Audie Cornish
00:23:26
He's seven, by the way. Everyone.
Roy Wood Jr.
00:23:27
He's good. You don't have to add that. You could have assumed he the 16 and a grandmaster.
Audie Cornish
00:23:32
I think it's important. I think it's part of the essential truth of the story. That's a callback. What they say in the comedy land.
Roy Wood Jr.
00:23:39
Maybe you could be a comedian. You have to look at how all of this is going and the thing that's weird is that you're just not sure if you're crazy or not.
Audie Cornish
00:23:55
'This will seem like it's not connected. But it occurs to me, that your father, who was a journalist and who was broadcasting right up until his death, right in the mid-nineties when you were in high school.
Roy Wood Jr.
00:24:07
Three weeks,.
Audie Cornish
00:24:08
He never stopped.
Roy Wood Jr.
00:24:09
No.
Audie Cornish
00:24:10
And it must take a great deal of strength and shift in you to come to a place where you actually feel okay with that. Even a pause, even not going as hard right as you have been just to reorient yourself.
Roy Wood Jr.
00:24:28
I mean, all I've ever known is this since I was 19, I started standup while I was still in college. I had no choice but to stick with it, because I did not get an internship in any summer, because the internship would have interfered with touring and just not touring, but just doing open mics all over the South. Yeah, I just but I think that recognizing rest is a moment to reset and then really come back out the gates twice as hard and smarter because clearly just banging, banging, banging and banging hasn't gotten me everywhere I wanted to be yet. You know, I'm not content, you know? But, you know, I think this is all part of the work. And I'm like, finally at a place where I can accept that. Oh no, rest is work, too. That's part of the thing. So, I don't know, maybe I thank my therapist for that.
Audie Cornish
00:25:29
Well, I'm looking forward to the spring out of your winter of discontent. I'm looking forward to what you come out of the gate with. And I'm really glad that.
Roy Wood Jr.
00:25:39
But that's what I mean by fear. You understand? What I say about fear? It's just you don't know where this is going. So.
Audie Cornish
00:25:46
I really appreciate you taking the time to talk with me and so candidly about so many things. This was really great.
Roy Wood Jr.
00:25:53
Absolutely. I respect you. I do have a lot of respect for you as a journalist. You do dope stuff, and and it's always good to sit with people who get it. Just put it that way.
Audie Cornish
00:26:16
Comedian Roy Wood Jr. Find out if Roy is coming to your town. His website is Roy Wood Jr. dot com. Find a link to that in our show notes. The Assignment is production of CNN audio. This episode was produced by Dan Bloom. Our senior producer is Matt Martinez. Dan Dzula is our technical director. And Steve Lickteig is the executive producer of CNN audio. We got support from Haley Thomas, Alex Manasseri , Robert Mathers, John Dianora, Leni Steinhardt, Jamus Andres, Nichole Pesaru, and Lisa Namerow. Special thanks to Katie Hinman. I'm Audie Cornish. And thank you for listening.