Roy Wood Jr. on Creating Comedy in Absurd Times

A standout even among the reliably hilarious ranks of Daily Show correspondents, Roy Wood Jr. has dedicated his entire on-stage and on-screen career to finding fresh angles and unexpected takes. A finalist on the 2010 season of Last Comic Standing, Wood first rose to prominence on radio, thanks to his facility with the lost art of prank phone calls; he went on to appear on such shows as Sullivan & Son, Conan and The Tonight Show With Jimmy Fallon, and also released his first one-hour special, Father Figure, on Netflix.

Wood was recently named the new host of Comedy Central's storytelling show This Is Not Happening, which means you shouldn't miss the chance to see him in a comedy-club setting. In advance of Wood's appearances at the Comedy Works downtown July 12 through July 14, we chatted with him about his new, angrier hour, his in-development pilot Re-Established, and why he'll never leave The Daily Show.

Westword: Between the absurdity of the news itself and a surfeit of competitors, it seems harder than ever to write topical jokes. How do you find a fresh perspective?

Roy Wood Jr.: I think the easiest way to have a fresh perspective on all of this is that the first thing you have to do is accept that it's true. I think the more you're in denial, the longer it takes you to digest the times that we're living in right now. Donald Trump is the president. There's no more talking about "How did this happen?" Maybe we can eventually figure that out, but in the meantime, we've gotta comment on what's actually going on.

That was a more therapeutic answer than I was expecting.

I really feel like we're in a place in our society right now where you can choose to laugh or you can choose to cry, you know? Even the people who do cry still need to take a break every now and then to come laugh for a little bit, so we're doing it for them as well.

Watching the news is exhausting in this day and age; does all the media exposure writing for The Daily Show requires ever get tiresome?

Yeah, it's funny, because when I first started at The Daily Show, I would spend a lot of time outside the office consuming media so I could be as sharp as possible. And then one day I decided that I didn't want to do that anymore. I said, "You know what? I'm going to just watch reality TV." It's counter-programming to the real world for me. I watch what I need to watch to get jokes and structure and things like that, but now I've decided that when it's time to kick back, it's time to kick back. Reality TV is like a brain cigarette; I don't know how else to describe it.


Some of your earliest media exposure came from making prank phone calls for radio stations; what are the qualities of a truly great prank call? What keeps people on the line?

I think a good prank call has to be either one street over from the truth or right on the nose, you know? One or the other. ... I's funny, because I wouldn't be able to do the prank calls I did back in the day anymore. I don't think I could do them now, because Trump has made everything laughable but true. I don't know if I would even have the mental capacity to invent a reality this crazy. If you told me ten years ago to do an unbelievable prank on someone, I'd, like, give someone an invitation to join the Space Force. And now there might be an actual Space Force, you know? The joke's on me.

Yeah, Trump kinda broke the comic exaggeration element of satire. There's nothing too absurd to suggest anymore.

Yeah. One hundred percent. Oh, my goodness, Trump might have been a good standup comedian. Lord knows, he has some interesting ideas. Donald Trump policies as joke premises would be amazing. If he was in the writers' room of SNL, his sketches would get made every week. What if I threw a Starburst at a woman? What if I invented a new military force called the Space Force? What if my wife wore a jacket that says "I don't care" on the way to an event meant to show that she does care?

Do you have any theories about that? Not to get too derailed from the interview, but I don't see how it could have been an accident.

No, no. Things are far too calculated in Washington for something to be random, even putting on a jacket. Somebody had to ask, "Hey, are you sure you want to do this?," and Melania had to say yes.

I'm going to pivot back to comedy: You’ll be replacing Ari Shaffir as the new host of Comedy Central’s This Is Not Happening. How did that come together?

So, yeah, Ari and the network split ways, and so the network came to me and asked me if I wanted the job. I think it's a great show, and it stands out in the crowded field of TV comedy right now, both scripted and unscripted. We're the only storytelling show across all channels and streams. And I think that's very important, and I think the show honors one of the major foundations of standup, which is storytelling. It's not something I take lightly. I didn't say yes just because it'd be something to do. Ari Shaffir built that show from the ground up and he created a place for a lot of comedians who wouldn't normally have the opportunity to be on television, doing exactly what they do best.

People do really seem to respond to storytelling shows. There aren't any on television but there tons of live shows and podcasts with a similar format. What need do you think these shows are filling for people?

Well, I feel like storytelling is the basis of human nature. If you look beyond television, a lot of the best songs tell a story or evoke a feeling. Movies and prestige dramas are telling stories; everybody's telling stories. On the show, we're just doing it in its most binary form.


What’s the word on Re-Established? Do you know if Comedy Central’s going to pick it up?

I don't know if they're going to pick it up. We're still working on the script, my co-writer and I. So fingers crossed. I think we have just as good of a chance of making it to air as anything else they're developing. It's definitely a show that I'm very excited about. You know, all I'm trying to do is have a little fun, but I do want to sprinkle a little bit of message into what I'm doing. Not a lot, just enough. When you look at the prison system, and look at it as a tool of rehabilitation rather than as a tool of punishment, I think there's a lot of truth that can be unearthed.

I can’t really think of any comedies set against the backdrop of the parole system specifically; what inspired you to want to tell these sorts of stories?

There are reality shows. There's one on A&E and another one on TLC. I think it's called Pitbulls and Parolees or something.

No comedies, though?

No comedies. Nothing ever. But the system is fascinating to me. Probation officers are the only branch of law enforcement whose job is to keep you out of jail. When you look at what happens even now with ICE and the FBI, or even local police — the breach of trust between law enforcement and citizens is probably the widest its ever been, at least in my opinion. I think somewhere in the midst of that are probation officers and parole officers who are trying to help; they're like part social workers, part law enforcement. To me, I think that what they're doing is more on the community level. It's community-based policing in a land full of people just trying to lock you up for doing the wrong thing. Even if they don't succeed, the fact that they're trying to help people do the right thing instead of punishing them for doing the wrong says a lot.

So theoretically, if Re-Established did make it to the airwaves, do you think you’ll still have time to be a correspondent? Or is that a question for another day?

No, they will have to fire me from The Daily Show, because I ain't quitting. I don't care what the hell I have going on. Steve Harvey has fourteen things going on at any given time, and somehow he manages to do them all. Radio, talk show, game show, you know? If Steve Harvey can do all that and stay a sane man, then so can I.

How do you feel about the hour you’re currently working? How is it different than the material on Father Figure?

Father Figure was an analysis of the world, and No One Loves You is an indictment of it. That's probably the biggest difference.

So that's the name of the current hour? No One Loves You?

Yeah, that's the new special. I'm taping it this week in Chicago.

Oh, wow.

It'll probably roll out at some point later this year. Father Figure was like me telling my son, "These are the things you should be aware of," whereas my message to my son this time is, "People are screwed up. People are terrible. Watch your back." And I fuse a little bit into every joke. It's an indictment of insincere sincerity, of people who claim to want to help find solutions to an issue. Just question everything and every one. We're so quick to indict corporations; we'll Twitter-mob a corporation into apologizing for something and we'll feel like we did something.

But you need to ask yourself, "Do they care about your cause or do they care about your cash?" And you should act accordingly.

Roy Wood Jr. will be at the Comedy Works from July 12 through July 14; showtimes and admission prices vary. Visit the Comedy Works box-office page to buy tickets and learn more.