Roy Wood Jr. Thought He Had ‘Daily Show’ Host Gig in the Bag

It’s been more than a year since Roy Wood Jr. left The Daily Show and he’s not looking back. This week, the comedian is dropping what is arguably his best stand-up special yet on Hulu and next month will see the second season premiere of his CNN comedy quiz show Have I Got News for You.

In his return to The Last Laugh podcast, Wood discusses why he wanted to make his yearning for connection the central theme of his new hour, Lonely Flowers. He also opens up about his decision to leave The Daily Show behind before Comedy Central brought back Jon Stewart and elevated his former correspondent colleagues to become rotating hosts—as well as what it’s been like to bring some much needed humor to CNN in the aftermath of Donald Trump’s re-election.

The last time Wood was on The Last Laugh, he was promoting his “America: For the Last Time” tour with The Daily Show’s Jordan Klepper. “I hate that we were right about that one,” he jokes of the ominous title. His new special, which begins with the prediction, “We ain’t gonna make it” has a similarly dour outlook for the future of the country.

“In this particular special, I was speaking more about the issues of us as a people,” Wood explains. “Like, I don’t think society is going to recover from the emotional separation and detachment issues that COVID gave us. But you could also apply it to the fact that there’s going to be a bunch of deportations. So yeah, there was definitely a little double entendre action with that phrase.”

The lack of connection among Americans is a running theme throughout Lonely Flowers. But there is an inherent irony in the fact that doing comedy at this level requires a unique bond with his audience.

“I think the relationship with an audience for a stand-up comedian is the most genuine of all the insincere connections,” he explains. “Because if you put a comedian in a room with 2,000 people, he will say any and everything that’s on his soul. But he is also saying it because he knows he doesn’t have to see those people again.”

Personally, Wood admits that he works through his emotions on stage before he ever brings a specific issue into therapy, or even “the actual person” that he has the issue with. “It’s easier to share what you’re going through with strangers, because the strangers aren’t going to judge you the way friends will,” he says.

“Also, strangers aren’t going to rush to try and give you a hug,” he adds, before joking, “Unless it’s John Mulaney‘s audience.” Wood explains that he opened for Mulaney a handful of times a few years ago. “and it was the first time I felt love back from the audience. It threw me off. I was like, stop caring about me! I’m on stage to feel despair, not warmth. The f--- is wrong with these people?”

Below is an edited excerpt from our conversation. You can listen to the whole thing by following The Last Laugh on Apple Podcasts, Spotify, or wherever you get your podcasts, and be the first to hear new episodes when they are released every Wednesday.

You have a joke in the new special where you say that you called up your mom and told her she could finally retire because you had The Daily Show host gig in the bag. You do add that it was a “true story,” so I would love to hear more about what happened there.

Yeah, I called my mom. This was right after I did the Correspondents’ Dinner, which was like a week after I guest-hosted The Daily Show. I was like, who knows, mom, you might be able to quit your job. And then, like, five months later, I’m resigning from the show. The morning the press release went out that said I was leaving the show, I called my mom and I told her, “Look, I think I want to leave the show, I think there’s some other stuff I can try and do, but I’m not going to be able to do that stuff while working at the show.” And it’s just a long pause, and then she just goes, “Well, I’m glad I didn’t quit my f---ing job like you told me to.”

And it was a leap of faith, right? You didn’t have something solid lined up.

Oh, no, no, there was nothing lined up. But it was the idea that to create the space for whatever is next for me—if there is something next for me—I need to create the space for it.

There was a really big change that happened at the show right after you quit, because they were relying on these celebrity guest hosts—I think to the detriment, somewhat, of the correspondents. Then, right after you left they announced Jon Stewart was coming back to host Mondays, but they also elevated the correspondents in a bigger way to host the rest of the week. So I was curious what you made of that. And did you have any regrets or mixed feelings, about your decision once you saw where it all landed?

No. I left the show before the Jon Stewart thing was even a rumor within the building. And before it was the correspondents being the centerpiece. So I don’t have any regrets, because I made the best decision I could with the information I had at the time. Even if I’d stayed and worked alongside Jon Stewart, at some point with all jobs, there’s a time… every job you have is a lease. It’s not an own. You’re not renting to own so sooner or later I have to start thinking about what’s next for me. And what do I want to build? What is my life going to be after The Daily Show? And I just decided that for what I do comedically and what people expect of me comedically, an election year would be the best time to try and figure that out. Once I had that decision in my head it wouldn’t have mattered, you know, who was coming in to host. I made that decision based on 2026, 2027, 2028.

You’re trying to set yourself up.

I’m thinking about what’s down the street and around the corner. I think what they’ve done with Jon Stewart since I left has been amazing and I’m happy to see it. I still talk to everybody in the building. Me and [Jordan] Klepper still did shows after I quit. Ronny [Chieng] and I still hate-text each other. So I’m cool with everybody in the building. I know Jon Stewart’s contract is through the end of this year. This is weird to say, but as an outsider looking in now, I think that whatever the destiny of The Daily Show is in terms of hosting, that solution is inside the building right now. Everybody in that building works hard and busts their a–-, man. So they deserve a shot to do it. I chose to do something different, because that felt safer for me. At least, if I jump out of the plane, I feel in control.

Because you were a frontrunner sort of in the minds of people to take over The Daily Show—even if they had no plans to pick someone to actually take it over—that must have led directly to the CNN gig, right?

It couldn’t have hurt! Correct me if I’m wrong, bro, but I’m pretty sure we are the only new political satire show to come out in the last two years. I do not believe there has been a new program introduced to the marketplace that swims in the same waters as The Daily Show and John Oliver and Bill Maher and all of them.

In terms of doing satire at CNN, are there certain challenges that have come up in doing a comedy show somewhere like CNN vs. Comedy Central?

There have been no issues at CNN. In fact, everything at CNN has been so dope that it’s part of the reason why I did not talk about politics at all in the new special. I taped the special in September, so the idea that any Kamala or Trump joke will still tonally work in January is tough. You don’t know who’s going to win the election. You don’t know if it’s going to be a riot. So that’s part of the reason why I didn’t do any politics in my new special, because I knew I have an outlet for political jokes that can be instantaneous. And in between dark weeks, when we’re not on the air, I can run down to the Comedy Cellar, crack a joke, and throw that up online and talk about Biden or Kamala or Trump’s Gulf of America bulls–-t. You don’t want to be the guy in a January comedy special talking about Trump saying they’re eating the cats and dogs.

The CNN show does give you that chance to kind of do things up to the minute of when they’re happening.

Correct. We keep waiting for an email from CNN going, “Hey, that joke you made the other night, could you not?” But we’re on Saturday night and they give us free reign. I mean, hell, they brought us on New Year’s Eve, I make a Don Lemon joke, Michael Ian Black makes a masturbation joke. No emails!

It does kind of seem like anything goes on New Year’s Eve But I did notice when you refused the shot from Andy Cohen, and then made that Don Lemon joke, that Andy and Anderson Cooper did not comment on it at all.

As they should have. They shouldn’t have to stop everything to get into the weeds of the politics of how and why Don Lemon was let go. And that joke was in defense of Don and what happened, and the idea that no, I’m not going to get drunk because I don’t know what happens in this place. I’ve only been here 10 episodes. But that’s what we’re trying to do with Saturday nights on our show. You know you’re not watching regular CNN when you see New Year’s Eve and so we want this show to be the same thing.

I don’t know how involved you are in the booking process, but I did want to ask you about Samantha Bee, who is now co-hosting a podcast for the Daily Beast. She talked on that show about her decision not to appear on Have I Got News for You because the other guest was going to be Republican Congressman Tim Burchett, who she strongly disagrees with. What did you think about her decision?

I have high praise and respect for Samantha Bee and her decision to not be on the show. We weren’t disappointed or angry or anything like that. It wasn’t like, oh, well, screw her. I was like, understood. For the people who don’t know, a lot of Tim Burchett’s policies that he stood for are extremely anti-women. He’s pretty much a down-the-ballot Trumper. So I respect Sam Bee’s decision. I will say that it doesn’t change the show’s M.O. of trying to have people on like that for the sake of conversation and accountability, which Amber Ruffin did beautifully.

You notably did not want to give him a fist bump.

Didn’t touch him! The idea that we’re on to be buddy-buddy and give these people a foot rub is not necessarily true, but I understand the argument about not giving them an audience. Or that it’s somehow validating their policies. I think that the last eight years we’ve tried to play a game of exposure “keep away” with a lot of the people who make terrible policies within this country. But I think that the last election has shown that there’s a lot of people that rock with it. So if we’re going to have a different approach to exposing the hypocrisy, anytime I have an opportunity to do that with the Republican in the seat, I would much rather do it that way than with a picture of them on the screen.

I don’t think Donald Trump is going to be coming on as a guest anytime soon, but are there people who you would draw a line and say, no, I’m not OK with that person being a guest on the show?

Any elected official that wants to come on this show, that wants to come on CNN, and have a conversation and crack some jokes and get their feet held to the fire a little bit on some policy issues, I would welcome them on the program. I would love for Ted Cruz to come on. The next time he swings through New York to get booed at Yankee Stadium, I would hope he would stop by the studio. Mitch McConnell would be great. I think when you get into the talking heads and podcast people who push the lies that the politicians co-sign, that’s where it gets a little messy for me. I’m not necessarily sure if those are the type of people I would have on. I’m straight on any white supremacists.

You mentioned towards the beginning of our conversation that you did not think Trump was necessarily going to win again. Now that he did and is about to be president again, late-night shows are grappling with how to handle him this time around. I think Seth Meyers made a comment on his show recently, like, “I can’t believe that I’m doing this again.” How do you think about that?

I think our job at CNN is to recap the news of the past week. That’s the job of our show, and it’s not all about Trump. I don’t think we can live solely in a place where every joke premise is, “Can you believe this f—ing guy?” We did that already. So I think all of late-night will be looking to figure out the new solutions.

Do you have any concerns about Trump or his administration targeting comedians, trying to censor what can be said about him on television? Because he has made those threats.

I don’t think a lawsuit is going to scare most comedians, because we don’t have money anyway. And also, threats of censorship, I would hope, is where the American people would draw the line. Because freedom of speech is the one thing that I think we all agree on in a bipartisan capacity. So we’ll see. But am I going to be sitting in a room with my writers, wondering whether or not this is the joke that gets me arrested or put on the train? No, I’m not worried about that.

Listen to the episode now and follow The Last Laugh on Apple Podcasts, Spotify, or wherever you get your podcasts to be the first to hear new episodes when they are released every Wednesday.