Roy Wood Jr. Breaks Down His Killer White House Correspondents’ Dinner Set

“I don’t think there’s a crowd that’s a more strange mix than this,” offers Roy Wood Jr. “It’s just too many different types of people, all in the same place, and you’re trying to figure out the joke that’s going to hit all of those people. And then, you have to keep in mind that there are people watching at home that could care less about any of those people.”

The comedian is calling Rolling Stone the day after hosting the 2023 White House Correspondents’ Dinner, which saw the longtime Daily Show contributor (and future host?) follow in the footsteps of comedy greats Richard Pryor, George Carlin, and Jon Stewart in roasting the D.C. media and political elite to their faces, including President Biden and VP Harris.

Despite hitting the afterparties till 3 a.m., including a private CBS News event at the French ambassador’s house and a TheGrio soiree at The Smithsonian National Museum of African-American History and Culture, the former filled with “a lot of diplomatic-immunity types” and the latter with Diana Ross and Byron Allen, Wood Jr. has generously given some of his time to discuss his entertaining stand-up set, wherein he skewered recently-fired cable news hosts Tucker Carlson and Don Lemon, Fox News’ $787 million Dominion settlement, and Supreme Court Justice Clarence Thomas’s sketchy relationship with conservative billionaire/benefactor Harlan Crow.

We also chatted about his guest-hosting stint on The Daily Show and the ongoing audition process to (hopefully) fill Trevor Noah’s shows as the next host.

This is probably the only time you’ll have Joe Biden open for you. How do you think he did?
Joe Biden did spectacular. I mean, spectacular. I can’t be that funny. We actually had a Rupert Murdoch joke that I decided on the fly to drop, just because Biden’s Rupert joke was so spot-on. It was a similar age joke, and Biden telling a joke about Rupert Murdoch’s age is safer as opposed to me doing a similar joke and people calling me “ageist.” I had a hard time navigating that and figuring it out on the fly, but it was a good time, man.

Can I ask what your scrapped Rupert Murdoch joke was?
I don’t remember the exact wording of it, but it was something like, “If Fox News loses another lawsuit, they won’t be able to afford the animatronics that keep Rupert alive.” That was the spirit of the joke, as they say.

Were there any other jokes that you had to scrap after the Biden set? Did you have Elon Musk material that ended up getting the chop?
There was some Elon stuff that I wasn’t able to get to, but we never even got into the Elon stuff. Some of the first stuff to go was stuff about Elon and blue checks and Bluesky. It just didn’t work. It was just too on the nose.

Which jokes did you feel went over best, and were there any that you felt should’ve done better?[Laughs] I knew that they were going to groan on the school-shooting joke, but that one was just written for the groan. That was one that we had lower in the set, but then I opted to move it up because that’s the kind of joke that you want to tell to set the tone, like, let’s find the edge and then come back from it. That was my approach to it. We had more DeSantis originally, but started trimming him for the sake of more Don [Lemon] and more Dominion. In one way, as a comedian, you’re talking about what people want to hear versus what everybody’s talking about, so I have to balance both things. We stayed more on Don than DeSantis, because DeSantis isn’t even a candidate yet.

And by spending a lot of time joking about DeSantis in this forum, you’d almost be anointing him as a candidate in a way.
Yeah. If it’s too long or if it’s too much.

You told a Clarence Thomas joke that was so brilliant: “We can all see Clarence Thomas, but he belongs to Harlan Crow. And that’s what an NFT is.” There are layers to that one.
[Laughs] I was sitting with the writers and we were just arguing. We were originally trying to figure out a way to compare it to other things that people try to explain, like CRT, but they sound confused on. And then it’s, “OK, no one can really explain crypto. People have tried, but it doesn’t come out the right way.” And then we thought, “Oh, but he owns him, and he’s not here,” and then it was this lightbulb moment: “A-ha! Clarence Thomas is an NFT!”

And that’s also you calling him a token, which is the sort of Easter egg inside that joke.
Yes, but we didn’t want to say that part of it out loud. We felt like, OK, if you get that part of it, great, but if you don’t, cool. It’s almost like a choose-your-own-ending joke. That was the real objective. We tried to play around with things like “Negro For Taking,” but we felt that went too far. We’d gone far enough. And it rewards the intelligence of the audience.

Did they tell you that any areas were off-limits in your set?
They didn’t give me any do’s or don’ts, but I know that at these events, especially with the sitting officials, when we talk about the Kamala’s and everybody else, they’re not gonna want you talking about them. But I can’t ignore what people are saying. I’m a comedian, and it’s my job to acknowledge the truth. The truth is that everybody’s saying [Biden] is old, and that [Kamala] doesn’t really do anything. So, it’s on me to get onstage and figure out a way to attack that truth. And anytime I insulted them, there was an acknowledgement of an achievement they did. I did a nap joke and alternated line-by-line between that and policy points. People shouldn’t take them to be mean-spirited. If you think my jokes were vile, that’s a personal problem.

Interestingly enough, we haven’t seen the kind of pushback that we normally see on Fox News regarding the host’s stand-up set at the Correspondents’ Dinner. I suspect it’s because they can’t really address your Tucker Carlson or Dominion jokes because it’ll just make them look foolish.
Fox needs to just sit somewhere and be quiet for a minute. That’s it. Be quiet. And with the Dominion joke, the thing I was trying to infuse into the subconscious of the audience was to set up the Smartmatic one and make people aware of the Smartmatic lawsuit which is coming. One thing I forgot to include was to ask Smartmatic not to settle so that we could get into discovery. And look, I’m friends with some of the writers at these companies. I’m not gonna wish for a whole network to fold. They just need to have a little more quality, care, and concern for the American people.

Did you say you have friends who write for Fox News?
I’m cool with one of the comedians that writes for Gutfeld! Every network has people that are gonna say and do certain things, and I’m not gonna wish the whole network to burn into the fuckin’ ground. That doesn’t accomplish anything. Fox News still reaches a group of voters. I hope they infuse it with more truth.

When did you first get approached for the gig, and why did you want to do it?
February was when they spoke with me, and the press release went out not too long after that. Comedians, we like punishing ourselves, and the opportunity to maybe say something worthwhile to people in power, that really felt like an opportunity that’s not offered a lot and you also don’t know when you’re gonna get offered it again. In comedy, in a lot of ways you don’t get to choose when you’re ready for something. You just get called on. I couldn’t say no. Then, I had to figure out how to prepare for my guest-host week on The Daily Show and also concurrently prepare for the Correspondents’ Dinner. I figured out in March that I couldn’t do both, so I just turned all my attention to The Daily Show and anything that I knew wouldn’t be on The Daily Show I would put in a little side folder. After my guest-host week, I had maybe three weeks to figure it out.

That’s not a ton of time for a gig like this.
Primarily, I went to the Comedy Cellar. I went to one or two other spots in town, but I’d say 90 percent of this set I worked out exclusively at the Comedy Cellar, just because they bag phones. I was very paranoid.

Your desire to, as you put it, “say something worthwhile to people in power” seems to be baked into you a bit. Your father [Roy Wood Sr.] was a decorated journalist who covered the civil rights movement, and you got your start as a radio-show journalist of sorts.
I kind of joke with people because my father did morning news, but I sat on the radio every morning and did prank calls and gave away tickets. I wasn’t nearly in his world, but once I got older and a little sharper, then I stepped into having more opinionated thoughts and perspectives.

Who did you assemble on your team to write jokes for the Correspondents’ Dinner?
It was a motley crew of stand-ups and writers, all with some connection to that world. My head writer was Christiana Mbakwe-Medina. She’s a former Daily Show writer. We had Amberia Allen, who’s a former Daily Show writer. Felonious Monk, who is just a sharp fuckin’ writer. He was a writer and contributor for The Nightly Show on Comedy Central. Matt Negrin, who’s a producer on The Daily Show but also used to work in media, so he has a good eye for media stuff. He’s almost the media watchdog at the show in a way. David Angelo, who’s also a Daily Show writer and stand-up comedian. He has some pretty good conservative viewpoints. And also Lily Blumkin, who’s a writer’s assistant at Daily Show, and Kalia Tison.

You mentioned on Twitter that you had to tear up the script the day Tucker Carlson and Don Lemon were fired. How did that switch things up for you?
There were two really important days in putting the script together: Trump Indictment Day, and Bloody Monday, as I like to call it. We had all of these other jokes about spy balloons and Marjorie Taylor Greene, and the more we looked at it we were like, “Nah. This is what we wanna talk about.” We had spoken briefly about potentially talking about the T.J. Holmes and Amy Robach stuff, and the more we started talking about specific scandals, the more it was just about scandals and how we’re all obsessed with scandals. That was where the throughline came. Then the Dominion lawsuit came out, and we didn’t think Fox was gonna settle that fast. That was a shocker. That threw things off as well. It was this constant evolution of, “OK, if we gotta talk about Tucker, and Don, and the Dominion lawsuit, what do we have to cut?” Our stuff on George Santos, and the audacity of his running for re-election, just became a drive-by joke.

How did the Don Lemon material go down in the room, because he must’ve had a bunch of media pals and former colleagues there.
I felt like the jokes got a couple of laughs. Whatever happened between Don and CNN, he still has friends and colleagues in the room, so I imagine that they weren’t crazy about it. But I do hope people understand that they were all just jokes, and within that I still took shots at CNN for hiring Charles Barkley. Like, if Don Lemon’s behavior on-camera is the problem, you’re gonna add Charles Barkley? OK, if that’s how you wanna play it!

What was the vibe like there? And did you have any surreal encounters? It’s such an odd mix of people.
Yo… in a matter of, like, ten minutes I met Gayle King, a Property Brother, and Brittney Griner. And later in the night I saw Kellyanne Conway just hangin’ out. Just hangin’. And Bill Barr. There was so much stuff going on that I didn’t even have time to talk about those people! It’s a weird place. It’s just weird. It’s not a gig you can prepare for, which I think is the biggest issue.  

I saw a photo of Chuck Schumer posing with Julia Fox on the carpet, which I think sums up how weird the Correspondents’ Dinner is.
I didn’t even see Julia Fox. When I was onstage waiting to go up, I was still texting with my writers who were literally sending me messages of people that are up there.

Was the Vanderpump Rules joke aimed at Tucker Carlson a last-minute addition to your set?
We did that in the writers’ meeting earlier that day. That was one of those jokes where I know who Lisa Vanderpump is, but I don’t watch that show. Then, my writers were trying to explain to me what the show is. And they were like, “Well, it’s like this, and it’s not like this.” And I was like, “That’s the joke.”

Did anybody come up to you after your set to complain?
No, not really.

You’d mentioned prepping for the Correspondents’ Dinner and your week guest-hosting The Daily Show simultaneously. How’s the Daily Show audition process been going for you?
I don’t know, man. My job is to show up and be where they need me to be. I don’t want to sound boilerplate, but who they’re gonna choose and what just isn’t my call. I had two weeks that were pretty good on the show ratings-wise, but ultimately my job is to just be funny. I enjoyed being the guest-host. But I gotta get my food too, man. Life just isn’t about you.

Do you feel like this is a job that you not only want but deserve at this point? Because you’ve been at The Daily Show since 2015.
I don’t think “deserve” is a fair word. It would be nice to have an opportunity to have a microphone, especially as a Black person, to address everything that’s going on in the world. If it’s not there with Comedy Central, then there will be opportunities to create something somewhere else, or just do something myself. I think we get into a dangerous place if we start saying, “It’s my turn. I’ve been there the longest.” They may want to go do something creatively different. I’m 44. They might wanna go young! Anything is possible. I don’t subscribe to any of that because I don’t want to fall into the ideology of, “I have to host The Daily Show or my life will be a failure.” It would be a blessing to have the opportunity to sit at a desk and talk trash about the world. The Daily Show is the ideal place, but it’s not the only one. I don’t know when they’re gonna make a decision on a new host, but I’m happy to be in the mix.

With the exception of Amber Ruffin over on Peacock there’s a distinct lack of Black voices in late-night television.
Oh yeah. There’s been a slow regression. Larry Wilmore on The Nightly Show used to call it “The Unblackening.” I call it “The Deblackening.”

The late-night landscape has transformed back into pretty much all white dudes. Robin Thede’s show was canceled. Samantha Bee’s show was canceled. Trevor Noah stepped down—
—They’re replacing James Corden with @midnight. Ziwe’s gone. Sam Jay’s gone. Desus & Mero broke up, but still. That’s just not a good situation. Now, those could be creative or budgetary decisions, but they all need to be considered. The late-night landscape is turning into something different, and we don’t know what yet. And I think it’s on me to start looking at what that new landscape will be, and start ideating a show that’s close to that, or figuring out how to evolve The Daily Show so that it matches that.