Whether It’s ‘The Daily Show’ Or Whatever Comes Next, Roy Wood Jr. Is Ready

The opportunity to permanently host The Daily Show has been a realistic possibility for Roy Wood Jr., Jordan Klepper, Desi Lydic (this week’s host), and several other contenders since it was announced that the show would turn to a long list of guest hosts following the wrap of Trevor Noah’s impactful run last year. Recently, CEO and President of Paramount Media Networks Chris McCarthy indicated that he has a “running shortlist,” though it’s anyone’s guess who is on it. Honestly, it’s the kind of slow burn process that might break a brain if you were on the inside, but from our most recent conversation (and previous ones), Wood Jr. is clearly and calmly looking at the whole board.

After our lengthy talk over Zoom, while he built a remote set for some Daily Show web content, it’s clear that Wood Jr. proved something to himself when he hosted, even if it wasn’t the full measure of what The Daily Show would be if he got the permanent gig. He’s excited by the possibility of being what he calls a “news sommelier,” guiding the audience through the good and bad while adding useful and unique context. He says he couldn’t say no to the opportunity to tell stories through a Black perspective that’s missing from late-night (historically, but especially in a post-Desus & Mero, Ziwe, and Sam Jay landscape), and he’s down to explore and satirize how news is disseminated. Wood Jr. is aware of the success of the guest host experiment (his stint, with its Jon Stewart cameo and ex-president arraignment included) and somewhat intrigued by the idea of a world where correspondents might be asked to carry more creative weight on a show where the guest hosts to continue. But that’s not what he really wants. He wants to host The Daily Show, but, and this is me summarizing: he can’t wait forever.

In our conversation, we discuss his thought process around The Daily Show and when it’s time to walk away from the table, the guest hosting experiment, the responsibility of hosting the show, and late-night term limits. This before discussing his approach to his latest high-profile gig: hosting The White House Correspondents Dinner, an event where, as he says, he’s focused on trying to figure out what he wants to say about where we are as a society in addition to being funny. And also maybe not setting in motion events that’ll get him haunted by Mitch McConnell.

I’ve been watching all the guest host shows, but you’re the only one where I used the free trial on one of those streaming things on TV to see it live. I wasted one of my emails from my spreadsheet for you.

(Laughs) Oh, shit. You burned your fucking email doc.

There’s going to be a nationally broadcast Mets game in May that I’m going to miss because I was like, “No, I gotta use my free trial to watch Roy.” But it was a good week.

(Laughs) Man, that was fun, bro. That shit was fun. The Trump shit helped. But for sure, in terms of having nerves about doing the job and can I do this, I feel like I’ve at least answered that for myself. If not everyone else. I feel like a lot of it is out of my control in terms of who they choose. But if they don’t choose me, it won’t be because I can’t do the job. So I worry about the shit I can control, man. That’s really kind of where I laid my focus. But thanks, bro, because that shit was fun.

Is that an example of the show that you would do, or is it not the full idea of what your show would be if you had it just because of the abbreviated timeframe with everything and the Trump news breaking?

No, I don’t think anything that anyone is doing right now in the guest host capacity is the totality of what they would do creatively. I liken it to a basketball tryout or the NFL combine. We need to know the fundamentals. The fundamentals of the show are having some degree of humor, being able to be compassionate, and being able to come through the camera. Can you read the teleprompter? Basic stuff like that. Once you get past that, then I think you can get into answering the bigger questions about, creatively, what would you want to do? Because we can’t explore the different creative avenues that a host would want to do until you know they can do the basics. There’s no point in discussing what kind of offense you want to run until we know that you can dribble and pass.

Being a correspondent is such a different thing. God damn, that was the biggest thing I learned. It’s just how much different correspondents are from hosts. Like, you know it, but until you’re asked to play a different position on the team, that’s when you realize it. Because as a correspondent, I get to come in and just be silly, but as a host, I have to be funny. But you also have to be, I believe, touching or have a warmth to you. So I think that part of it, that was a new feeling, because I feel like I haven’t had to be like that since I did morning radio, bro. Even with morning radio, it was only on days when there was big news.

I was doing morning radio when the Trayvon Martin incident first happened in Orlando. So being on air and taking calls at what was such a visceral moment for society, where normally you’re supposed to just fucking be funny for four hours in morning radio, but then on this day, nah, you don’t get to be funny. You have to also have some emotion. So I’d say that’s probably the biggest difference between the two roles. When the Tennessee Three happened, we had already had the show kind of set. The jokes were about the possible expulsion, and then it turned into an actual expulsion. So now it’s like, “Oh, fuck. Okay. Maybe this isn’t funny yet. Maybe we have to wait to see how all the facts start happening.”

It probably goes without saying, but do you feel a greater sense of responsibility with that, and was that anticipated, or more than you expected?

You know there’s a responsibility, but you don’t realize until you actually sit down in the chair and go, “Oh, okay.” We’re also kind of guiding people through the news, and in some cases, it’s bad news. Sometimes it’s good news. I think the first night, I jokingly called myself Uncle Roy, just kind of on some, “That’s what your uncle does. Your uncle helps you, the good uncle. The good uncles help you through tragedies and problems and issues in the world.” It was a blessing to be able to do that.

Do you feel if you had that role permanently, that the weight of all of that would wear you down after a time?

I don’t think the job of Daily Show host is anything anyone should be doing more than, I don’t know, five to seven years, if that. It’s like the president. Two terms. There should be term limits on late-night hosts. I would argue that part of why John Oliver is so energetic is because he’s smart enough to take those times to rest and have a couple of months just away. There will be plenty of chaos when we return.

If they go with somebody else, do you envision yourself sticking around for a while, or are you starting to look for something else at that point?

I think it depends on who they choose to host. I think my staying at The Daily Show, if I’m not a host, starts and ends with whether or not that host wants me there as a correspondent. Then, secondly, I think I’ve earned the right to at least look at the market and see if there’s something else that I want to do above and beyond The Daily Show, because if I’m not serious about being a correspondent through the election, as a correspondent I have the responsibility to get out the way so that they can replace me as quickly as possible so that new correspondent can learn the ropes before 2024. To me, that’s the big thing.

It’s not fair to the new correspondent to be broken in the middle of a presidential primary. The audience needs time to warm up to these new faces and to the new tone of the show. I think that’s the thing that when I talk about honoring the show and what the show’s mission is, I think it’s that, and that’s not just about me going and hosting something somewhere else. This could be also scripted stuff. I was blessed enough last year. I sold two scripts. One, I was EP on, and the other I was attached to star. Neither one of them went the distance, but to even be in that space, that’s something worth considering.

I think that myself and the other correspondents, as late night starts this new metamorphosis… late night is no different than TV as a whole. It’s contracting, and when it comes back out of this cocoon and expands again, it has to expand into something different. It’s not going to be a repeat of what it has been. So where I fit in that as a co-star or a sidekick, that’s not completely for me to answer. There are constructs under which I would consider it (staying), but for lack of a lack of a better phrase, if I have an opportunity to drive a car, then it has to be the right situation if I still want to ride shotgun somewhere else. You know? We’ll look at that when the time comes, man, but everything’s on the table for me right now.

You have a really refreshing, really clear view of things when we talk about this stuff that I really appreciate. You’re doing what anybody would do. They would evaluate their options. It sounds like you’ve got a plan waiting for a plan at least to kind of reveal itself.

Yeah, or the writer’s strike could hit and it could change Paramount’s decision schedule. When they’re going to choose a host is as important as what happens if myself or some other correspondent gets an opportunity that comes before Paramount is ready to choose.

Have there been any indications about a timeline for that?

No. All they told us is that we’re doing guest hosting through June. That’s the only thing I’ve heard. There was an op-ed where they were hypothesizing guest hosts in a permanent sense and letting that be the new norm. So any and everything could be on the table. I just think that the way entertainment is going right now, if you have an opportunity to have a project that you can get off the ground and work that project at a time where everything is contracting, I think it is a very, very dangerous gamble to pass that up to wait on something else.

Yeah. And even if it’s the dream job, the dream job is the job that has security.

I’ve lost enough money at the casino to now know when it’s time to leave the table. I’ve been very blessed the last seven years, and whatever opportunity I get first that lets me leave the table, I’m leaving the table. I’m not splitting aces. I’m not doubling down. I’m not going to risk it all. “Let it ride! One more roll!” Nope. (Laughs) I got a kid to feed, man. I can’t sit here and wait around for corporate politics. Because that’s what a lot of this is, man. It’s not even creative. Our ratings are up. So yeah, it’s probably good to just keep having guest hosts.

It’s cheaper too, I imagine.

Yeah, I’m sure it’s way cheaper. And I have a lot of respect for the brother that wrote the op-ed, and I don’t say this in some challenging way, I just think that if The Daily Show is to parody the news, the news gives you the same faces every night because there is a trust that comes with that. I think that once people trust a host and know where the host is coming from, it gives the host so many new places to go with their humor. Honestly, I would’ve argued that every guest host should have gotten two weeks in the chair, just because you need a week to get used to it. The audience needs a week to get used to you. Then, let the second week be the money. That would’ve really been cool.

It would’ve really been cool to see how Wanda Sykes did, because D.L. Hughley’s first day was the day that the Tyree Nichols tape was released in Memphis. If we had done back-to-back weeks, that would’ve been a Wanda Sykes week. It would’ve been interesting to hear Wanda’s commentary and stuff like that. Even with the Trump arraignment, that came in after rehearsal on Thursday for John Leguizamo. As much as Leguizamo as a native New Yorker and a Latino, and as much as Trump’s well-documented, “Lock them up, kids in cages” strategies with immigrants, that would’ve been an interesting perspective to have as well. I think that, not just The Daily Show, I think that new political satire works best when the audience is getting it from someone they have a relationship with, and it takes time to build a relationship.

I’m team host. (Laughs) I get why doing the guest host thing could be cheaper in perpetuity, and could be better ratings in perpetuity, but sooner or later, you’re going to catch the wrong host during the wrong tragedy. And it’s going to be weird.

Switching gears, with the White House Correspondents Dinner, I know you’ve interviewed Obama. I know you interviewed Biden.

I got one question with Biden. That wasn’t a whole interview. I got half a question, but yes, I have talked to Biden.

Do you feel nerves there, or are you used to it at this point?

There’s nerves. I’m more trying to figure out exactly what it is I want to say to the bigger whole of where we are as a society. I’m more concerned with that than I am joke to joke. I don’t care if someone doesn’t like a joke I make. I’m indifferent on that. As a comedian, your job is to point out hypocrisy, and some people don’t like that pointed out, so there should be dissenters. Has there ever been a comedian that did the Correspondents Dinner that was like universally loved by all? I’d say maybe Cedric the Entertainer. Then, also, you could do it one way, and then after the fact, the perception of it changes.

Seth Myers was great until Trump got elected. Now, “Seth Myers is bad.” “Stephen Colbert was terrible.” Until you really look back at the Bush Administration’s record, and now you go, “Stephen Colbert, brilliant.” I don’t think, as a comedian, I can be attached to, “Did you do good or did you do bad? Did you bomb” or whatever. I just need jokes that call out the BS in this world, and just figure out a way to make it fun. Above all, my job is to be funny, and if you can sneak in a little bit of creative activism and stuff like that, then so be it.

The biggest issue with the Correspondents Dinner is that the news keeps changing. Every time I open my mouth, Clarence Thomas is taking another bribe or some other thing, there’s another shooting. Is Don Lemon back on the air again? [Edit note: the news cycle proved Roy’s point this week] I don’t know. It’s always something, bro.

I think you can definitely write the Clarence Thomas material in pen because he ain’t going anywhere. It’s not like he’s actually going to face consequences.

Yeah, exactly. There’ll be no consequences.

Of course not. I love people getting bent out of shape thinking that there will be. I want to live in the world that they envision, but yeah, no, unfortunately not.

We are in the land of no shame and no consequence. That’s the land we live in.

Do you have any specific places you don’t want to go to in terms of how far you push into certain people? The Biden stuff, obviously there’s Biden age jokes, and then there’s Biden dementia jokes that people make. How far do you go on something like that?

I don’t know. I don’t know. I think everything’s on the table except for Mitch McConnell because he’s in the hospital.

Is he still?

I need to double-check, but for now, Mitch McConnell is safe. If he gets out of the hospital, we’ll check his vitals before I go on stage. You don’t want to be the guy that does the joke that stresses out Mitch McConnell. It’s one thing to do a joke that gets Trump elected, but you don’t want the passing of Mitch McConnell because of stress created from a joke on your hands. That’s not a ghost I want visiting me. So Mitch McConnell’s off the table for now, but my humor has never been, as far as I’ve tried to make it, anti any group.

No. You’re not mean-spirited at all.

But I’m anti-politicians who impede political progress. For that reason, Democrats are on the chopping block too.

I was going to say, “Oh, that’s pretty much all of them.”

Yeah. That’s pretty much all of them. If you got Tim Scott proposing a police reform deal that Democrats filibuster, I need to know why. When y’all promised us some degree, but it’s a room full of people who all want credit instead of just wanting progress. Everybody wants credit.

‘The Daily Show’ airs Monday through Thursday on Comedy Central. The ‘White House Correspondents Dinner’ airs April 29 live on CSPAN.