Roy Wood Jr. began his comedy career in 1998 at the age of 19 while studying journalism at Florida A&M University. He took off like a rocket, hosting a popular morning radio show in his hometown of Birmingham, Alabama, starring in the TBS sitcom Sullivan & Son, performing on Conan and David Letterman, and making the rounds at comedy clubs nationwide. Now a huge hit as a correspondent on The Daily Show, the comic’s double-decade commitment to comedy is paying off in a big way. A few days after taping his first one-hour Comedy Central special in Atlanta, Wood Jr. took some time to talk to me from his “noisy-ass corner office” at TDS about politics, prank phone calls, and puzzles.
You just had your first Comedy Central one hour special. Congratulations. How was that experience?
Thank you! It was fun. Atlanta was a blast to say the least.
Were you nervous?
I was more nervous about remembering the material than anything else. It wasn’t stage fright. It was more the technical aspects and wanting to nail the performance. It was more, I hope I don’t forget the jokes. Because for me, my biggest fear is forgetting the jokes. More than being booed. With some of my jokes and my material, there is still some nuance to the performance of it. So I’m very methodical. I want to have the right inflection, stage blocking, all of that stuff. For me those things are really important and I want to pay close attention to it.
What kinds of things do you do to prepare for a standup show?
Well, thankfully moving to New York has definitely made me a sharper comic. It’s put me in the position of repetition. I watch video of myself and critique myself – comics are our own worst critics, so it’s perfect. I listen to the audio of the joke and then figure out the best way to perform it. Or whatever nuances I can add to the joke. But I can’t work on the performance until I really know the material. It’s like learning the song before you go on tour for a concert.
Your delivery is amazing, so your efforts are clearly paying off. How do you come up with your jokes? What’s your process like?
Chappelle said something years ago in a magazine interview about how every comedian needs to understand how their joke machine works. Meaning, identify the things that inspire your creativity. For me, it’s things that frustrate me or put me in a weird mindset. A lot of my comedy is about analyzing petty minutiae of the world and also trying to find a third perspective on something. I tend to read a lot, to watch things that annoy me. Finding things that evoke emotion. Because if I have emotion, than I have somewhere to start from in taking that stuff on stage.
What kinds of things do you read and watch to get that emotion stirring?
PBS, Viceland, TLC. I like IDTV for whatever reason. Where it’s just all crime and criminalistic stuff going on. That’s one of my personal favorites, I enjoy that stuff. I watch network shows too, of course, I watch stuff to be entertained. But when it’s about educating myself and really probing into curiosity of the world – I like highbrow and lowbrow. So a good documentary for me is just as valuable as a reality show creatively.
You got started in Birmingham, Alabama. What’s the response been back home to your success?
Birmingham has always been supportive, that’s where it all started. So by and far, I’ve always felt like I have a good place at home to be able to do things. It’s always been good to go home, but the thing that sucks is that I haven’t been able to perform at home in almost five years now. At some point I want to get back home, but I’m away for a good reason, so in that regard it’s not the end of the world. One night in Atlanta, there was a sizable amount of people from Birmingham in the audience which made me feel really good, to have people from home coming out to the show. As much as I can, I try to represent Alabama positively because lord knows the politicians there don’t give the people very many reasons to support the state of Alabama.
Were you funny growing up?
I don’t think so. I didn’t get funny til high school. I used to ride the bench when I played baseball. It was one of those things where you’re bored on the bench all day so you start cracking jokes and picking on people from the other team. It was fun, it was very much fun. That was probably one of the first instances where I understood that I had a sense of humor. But for the most part I was very quiet. I didn’t come out of my shell until college.
I read that you started out in journalism and then took a turn into comedy. What got you going down that road?
I took a class in public speaking and we would do impromptu speeches. That was kind of like my first open mic in a way. It was an opportunity for me to get on stage, to get up in front of a group of people. It was on a serious topic, but I would get laughs. That was sort of the first snake bite, if you will.
Do you feel like comedy is an opportunity to change hearts and minds?
For me comedy is more of an opportunity to escape something going on out there in the world or to look at it through a funnier prism or in a way that you normally wouldn’t have. Can comedy change hearts and minds? I guess, maybe it can. That’s not what I’m really setting out to do, I just want us to be able to better understand one another. And if someone is moved by my comedy to feel differently or to look at something differently, then I’m appreciative of that, that’s great. But I’d be lying if I said that was the goal out the gate the moment I step on stage. I feel like if you do that, you’re measuring yourself by your ability to change minds rather than make them laugh. You can still laugh at someone even if you didn’t agree with them.
I can imagine that would make it hard to be relaxed and loose.
Yeah, I’m not interested in being this guy on this comedy mission from God. I mean I could be. But it’s not likely.
You’ve been on The Daily Show for over a year now. What’s that like?
It’s been a really fun time. The political season is crazy and thankfully Trevor and everyone here at the show has been giving the correspondents the opportunity to really infuse their own political opinions and perspectives on the political scene here in the country. It’s exciting man, it’s really an exciting time. I feel very fortunate to be here.
You’ve been traveling all over the place talking to people. Does anything surprise you?
I think the one thing that definitely always throws me off is how honest everyone is that we talk to. I don’t know how to explain it, but these people we interview for the show are very much steadfast in their views. Because people say, I can’t believe it, no way someone said that, but hell yeah, yes way, 100 percent they did say it. There are people with ridiculous views – well what we consider ridiculous views of the world – that want to be heard. They want to put their face to this particular feeling. I’m blown away by that blatant level of honesty from people.
Is it ever challenging to control your own reactions?
Yes, but thankfully the thing that helped me out was doing prank phone calls when I first started. Doing prank phone calls when I was doing morning radio for about ten years put me into a different mindset to do these interviews. Because these interviews aren’t prank phone calls, but there are funny moments where you can’t lose composure otherwise you lose all of this work that you put in. All of the things you were trying to do can get obliterated because you can’t stop giggling.
What’s the craziest reaction you’ve ever had to a prank phone call?
I prank phone called a guy in Cleveland who was not pleased that I pulled this prank on him. He showed up at my show to fight me. This was four months after I did the prank, mind you. He was pretty, pretty motivated.
What did you do?
I shook his hand, I apologized. He came to the comedy show, sat up front, and didn’t smile the entire time. I guess that was his pre-game intimidation.
Terrifying. Did you have any weird shows when you were starting out?
A guy couldn’t pay us one night because he didn’t sell enough tickets, so he offered to pay us in cocaine. He even offered to show us how to cut the cocaine so we could make more money from it. And I quote, “you’ll make triple what I was going to pay you if you do it right.”
Oh no.
So that was a night that I ended up doing a free show. It’s an interesting life. I’ve had shows where I’ve been called the “N” word from somebody in the crowd, shows where people want to fight me, but I wouldn’t trade a single moment of it.
Sounds like you’re pretty resilient.
Yeah, you don’t have a choice. This is the only thing I’ve done since I was 19, what am I going to do, change careers?
If you did change careers, do you have any idea what you would do?
I would probably try to slide back into journalism, do something over at ESPN. Stuart Scott was an idol. That was someone I really, really liked. Either that or a firefighter, that was on the list as well. You’ve got to mix it up sometimes.
Is there anything people would be surprised to learn about you?
I enjoy puzzles. So there’s that. They give me that mental stillness, which also helps with performance.
You’ve had some incredible moments of political satire this year. Do you enjoy doing that kind of comedy?
Yeah, it’s nice to watch the news and see oh, here’s some hypocrisy, here’s some things that aren’t being talked about. Those things are vital to the political process. At the end of the day that’s what The Daily Show was built upon and the best way for me to honor the work all the political correspondents before me have done is to come at this from the same angle of attack. There’s a lot of legacy up here and I don’t want to be the one to screw it up.
