NBC Nightly News with Tom Llamas - Roy Wood Jr.'s complicated past shaped his comedy career

Episode Date: December 5, 2025

In this episode of "The Drink,” Kate Snow sits down with comedian Roy Wood Jr. to discuss his new book, "The Man of Many Fathers.” Best known for his years as a correspondent on "The Daily Show" — and now the host of CNN's "Have I Got News for You" — Roy reflects on the challenges that have shaped his career so far: a complicated childhood in Memphis and Birmingham, a college arrest, and even time spent sleeping in his car while traveling the country to perform stand-up."The Drink" is Kate Snow’s interview series featuring candid conversations with actors, authors, athletes, and visionaries — all over the beverage of their choice.Watch every episode of "The Drink" now at NBCNEWS.COM/THEDRINK. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Hey everybody, Kate Snow here. This is The Drink, my series all about how folks got to the top of their field, and I cannot wait for you to hear comedian Roy Wood Jr. You probably know him from his years as a correspondent on The Daily Show. Now he's the host of the CNN program, Have I Got News for You? He has written a great book called The Man of Many Fathers. We talked over two old fashions. First time anyone has ever chosen my favorite. favorite drink, by the way. We were at the Jupiter restaurant in Rockefeller Plaza. You're going to want to hear how Roy pushed through a lot of adversity to get where he is today. A complicated father, an arrest in college, many nights spent sleeping in his car while he traveled across the country to do stand-up. We bonded over driving K cars in the 80s, anyone, and loving jigsaw puzzles. As always, you can watch all of our episodes online, too, at NBCNews.com slash the drink. Roy Wood Jr. Is this an old-fashioned?

Oh, yeah, old fashions. Yeah, I don't know when I transitioned to old fashions, but I feel classy not. When you're drinking dark liquor, you want to have a little bit of lightness to it because you want people to take what you're saying, serious. Yes. Because if the liquor get a little darker than this,

this could turn to club shay-shay real fast. And I say they would respect because they just get club shesh-shay, and we was drinking dark. In all the drinks we've done, nobody's ever chosen my favorite drink. The old fashion. Well, then that means that we're kindred spirits. There we go.

Roywood Jr., you're a comedian. You're on the daily show for a lot of years as a correspondent. Now you've got, have I got news for you, the host of that. We're in Jupiter and Rockefeller Center down the concourse. Yeah, yeah, down here next to the ice rink that I never go on. Never? You could do it right now. I would never ice skate again.

I tried twice. retired. I have this fear of falling and somebody skates running over my fingers. Yeah, I get that. I get that. I think I have that same fear. It feels irrational, but I feel like if I dug deep enough on the internet, I can find something close to that, and it would scare me or not doing it. But yeah, my point is I'm never down here. Yeah, I got you. Thank you for having me. Thank you for coming. You have a book, The Man of Many Fathers. It's basically a tribute to your son, or you wrote it kind of for your son, right? Yeah, but you end up being a a journey for myself.

Yeah. There's the thing about a book. Like with stand up, you know where you're going. With TV, you know where you're going. But a book, you're discovering things about yourself along the way. As you write. For me, the book started as a journey into basically leaving kind of like a little bit of a notebook of who I am in terms of my values for my son to pick up.

And when I started looking at what my values were, the more I realized I didn't get most of those from my father because he died when I was 16. I got it from people within my community, people that I met only once, random co-workers, comedians. And so it just became this beautiful monage of characters. And, you know, my mother's still with me, thank God. But I still have to make a chapter about her as well

because I do have a lot of values from her. But what I found in my life is that just subliminally, intrinsically, whatever you want to call it, I find myself seeking out the guidance of men. Anytime I was in the orbit of someone that I felt I could glean something from. There was just kind of a gravitational pull to them. And so that's what the book became.

And I think the biggest thing I had to learn also was about letting go of any resentment I may have had because, oh, you didn't get, like, we grow up older. You go through this phase where you feel like your parents didn't do enough. And yeah, why didn't they do that thing? And then you realize, oh, I'm a father now. I can't hold on to that. I got to look at him and figure out what was the best part. of him and then do that with my son. Your dad, it's complicated, right?

You grow up in the beginning. You're in Memphis with your mom alone. Then you guys go and move in with your dad. Yeah. But he's got a girlfriend on the other side of town. Yeah. It's complicated. And two kids.

You had two kids. And you're one of 11 kids that he had. And my mother's only child in the 9th of 11 children by my father. So you don't get all of your father when there's 11 of you. Yeah. He's got to kind of spread him. around him. Although he did, he would take you, he was a radio, he was a radio guy. Yeah, he was a radio guy. He was a commentary. Yeah, you know, and news commentary about very hard issues affecting

black Americans. He didn't do cupcake stories. Yeah. If it was struggle, conflict riots globally or is in South Africa. He was there. No, and every riot in the 60s. So he definitely made contributions to the betterment of our society and my race. So I have to, acknowledge that wholeheartedly. But yeah, at the house, sometimes you didn't always see them. And so you grow up with that and you have to reckon with, well, how did that affect me? How did that change me? How did that make me who I am? And the book is just a beautiful journey into that part of my life. I did not know the places this book would take me emotionally when I sat down to write it. There's so much in here, but some of the stories about when you're young and

your dad would sometimes turn off the power or the heat on you and your mom. Yeah. My spouse was a great winner. And so my parents got into an argument sometimes, money is the thing that would be taken away. And so the gas might be off. You might come home one night. There's no heat in the house. You come home one night.

There might not be light. But what I learned from my mother in those situations was you still got to finish your homework. Life has put these circumstances in front of right. us and that's unfortunate but the work remains it seems like you also learned self-sufficiency you you were working when you were in grade school right i think about that and how working coming home some nights and the power being off and my mother not trying to figure all right well how are we going to pay the reconnect fee if he's tripping this week you learn to start squirreling away cash you learn to at 13 years old to rake leaves, you learn how to encourage employers to violate child labor

laws so you can work 30 hours a week at 15 and 16. You did that? Yes, just so there's enough money tucked off. I got to make sure that I got enough acorn stored away because the storm's coming. The storm's coming. And the storm may not ever be coming. And so I worked probably way more than I should have. And I think a lot of it also was rooted in not wanting to be a burden to my

mother. My mother's in grad school. My mother's putting all of her money into getting secondary degrees to get a better job so she can get us out of this situation. Which she does, right? Yes. She becomes... But I don't want you worrying about me. So I'm going to go work these 30 hours. My GPA is going to be a two-four out of high school, but I'm going to kill the standardized test. So don't worry. I'll get in college. Like once I figured out the hack of, oh, I just have to do good on this test and I still get in, all right, cool, I'm going to go back to subway and do another shift. Wow.

And so that type of tenacity and focus is exactly what you need to make it in entertainment, but because you're self-reliant, once you get to a certain plateau where I am career-wise, you need people, but you don't trust anyone because you've never, you've never worked with enough people. To this day, Roy, is it hard for you to trust? to a degree. And you're sharing it, and I mean, people, it resonates. Like, I told you, I couldn't put this down.

I was just, like, chapter to chapter. I don't even, like, even getting arrested for stealing credit cards in college, that wasn't about being cool. That wasn't about chasing an adrenaline high. That was, oh, I don't want my mom to worry about me. You go off to Tallahassee. Yeah, the Florida A&M. Yeah.

You got in college, you're there. What happens? I mean, like, if you're talking about, like, the actual, the ideation of, like, oh, here's the impetus for it. I went to a gas station. This is 98. This is the first years of pay at the pump. And back in the day, a credit card receipt had your full credit card on it.

And your name has it appeared on the card. Jackpot. And I was 18 at the time, we would take those cards and order pizza and I would just sell pizzas on campus. Did you purposely get a job at the post office on campus? No, it was right. No. I registered for workstation. and the only thing left was post office

because post office is boring and nobody wanted to do post office and then I got the job of the post office and I was like, jackpot. More credit cards. Yeah, credit card began mail to the post office for a student and we would intercept it and take it in by clothes and sell them

and then we got caught immediately. And so I got suspended from school because of that. I almost expelled, should have been expelled. And during that suspension, that's when I started doing stand-up comedy. Why right then you go, I'm going to do stand-up comedy now?

Because I thought I was going to prison. I'd always wanted to do comedy I've just never had the guts So that was like such a scare That you're like, I've got to do this thing I've always dreamed of doing it I got arrested, I'm going to prison in six months That's my time to do literally anything

I've ever wanted to do on earth Comedy was on the list I went to court, I got probation That was 1998 You didn't get any jail time No, I got probation I don't know how it happened But it happened

And now we sit here And that's what started my career After the break more from my conversation with Roy Wood Jr. About how he built a career in comedy through years of hard work and how Wendy Williams helped him land that dream job as a correspondent on The Daily Show.

Stay with us. You start doing stand-up comedy. It seems like for a number of years, years. You're doing the stand-up. You're doing some TV. Working day labor. A day labor. Doing morning radio. Yeah, I got my degree in broadcast journalism when I got back into school and started interning at a station in the same city that my pops was a household name. I have two older brothers who are household names on the TV journalism side in the city. So kind of in the family footsteps, if you will. You have some connections. Yeah. But like those first, I don't know,

ten years maybe how would you describe that period skinny very skinny skinny skinny as in physically skinny not physically skinny i slept in my car a lot i slept in truck stops that was when i got a car i started yeah on the greyhound wait did you have a k car a Dodge aries 987 i had a car yes lord here's to the headgass yet you crack your head gasket I don't think so. Oh, okay. You weren't driving that harder time, right? Correct that here, gas can.

Maybe. I don't know. I don't remember breaking down. Every child should have a car with a check engine light on. Yes. Every teenager should have that. But they don't now. An old beater car.

Yeah. But the problem now with new cars today, they've made them so that regular people can't fix them. They put special screws and it's all techie tech and computers. It's all digital. Yeah. So you can't fix it yourself. We got on a huge tangent about it back.

I'm sorry. I'm the one that did it. Because when I read that, I was like, wait, I had a cake up. So, yeah, so you were describing the skinny years. You know, those first 10 years were very skinny, but I learned a lot. You know, I went everywhere in that car from Birmingham up to South Dakota, down to Miami. I drove all the way to Denver. If I was in a city more than two days, I got a day job at a temp service or I would do day labor.

You described working in a church, sand in the floors or something. Yeah, they're building and just construction jobs. You name it. I did it. Doug Ditches picked up. up trash on freeways. Like, I'm in a city for four days to tell jokes at 8 o'clock at night. I wake up in the morning, it's 8.45. And you're chilling for 12 hours? No. Not you. Go work. Go do something. So when does it change? When does what change? I don't know,

your life. The drive, the hustle. I mean, everybody knows you now. How did that happen? Okay, but I think you're equating notoriety with success. Fair. And I don't think they're the same. Yeah, they're not. In the eyes of everyone else, it's like, oh, wow, people know you now. Yes, I would say the Daily Show. People were aware of me.

I was a comedian. And Conan O'Brien, shout out to Conan. You know, Conan was a guy that put me on TV every year at a time where nobody would put me on TV. The only people would put me on TV, there was a four or five-year stretch where it was Conan O'Brien and ESPN. That was it. And what's wild is at that time on ESPN. was really just a training ground to prepare me for the Daily Show. And so I do Daily Show 2015 and everything took off.

But I'm just, I'm lucky. Like, there's skill, but then luck is still a part of it. I don't even get to go do the Daily Show audition. If Wendy Williams, like I opened for Wendy Williams the month before the Daily Show audition, the money I made from opening for Wendy, was the only reason I could afford to move to New York. Wow, really? So you get lucky, yeah, they pay your little moving fee,

but the money you need to survive week to week until those first couple of checks start rolling it. And when you start in TV, even with the daily show, you know, making a lot of money. I'm so grateful not only to Wendy Williams, but hell, I was on tour with her, and she just wanted to let me go audition. Wow.

When you're on tour with someone and when you skip one city as an opening, traditionally you are fired. that is the precedent in the industry oh you can't do all the cities we'll do none of the cities and i go i can do them but this one day can you please let me go to new york and audition for the daily show and what she said she said changed my life after the break more from my conversation with roy wood junior on his surprising decision to leave the daily show and why you might see him on the big screen soon stay with us

2023, you do the White House Correspondence dinner. And then that same year, Trevor Noah was leaving, right? They're going to find a new host. In some interviews, you say, I'd love to be the host. Yeah, I would have. I would have. But it didn't seem like what the process would be, would be something that would be clear. If you were deciding to stay at a job and I told you I don't know

who your next boss is going to be. I don't know if I want you to be the boss and we don't have a clear structure on how we're going to look for the next boss. You stay. That's why you decided to leave. Yeah. Yeah. This is before John Stewart. Yeah. He's committed to come back. This is pre-John Stewart. I get it. I think some people were surprised though, right? Like there were people who were like, wait, he was going to get the job. That's one way to think that, but I don't think it was ever promised. It was never a promise. I mean, it's not like they said, hey, Roy, we kind of like, yeah.

Yeah. It was just, you're great. Hussim and Hodges great. We think he did a good job. Even the Hossa news had, like, kind of surprised me when they decided to rescind the offer from Hosson as it was reported, because I thought it was going to be Chelsea handling. And my brain, I'm like, okay, woman for sure. Chelsea, Sarah Silverman, outside Chance Leslie Jones.

Then the question becomes, okay, will Chelsea or Sarah want me there? Let's turn over with correspondence when there's a new host. Okay, will I fit in with that? Well, I don't know. Let's see. Leslie, I used to live in the same apartment complex in L.A. Really? We good.

I know my job's safe with Leslie. But not knowing what your structure was going to be, I need to do the thing that I believe gives me the most stability now. I love everybody over here. These are my friends. I was still on a daily show email server for a month. I don't even know. I was giving staff emails. They didn't even know you were on there.

Christmas party invites. Come on. They figured it out. Yeah, eventually. I believe my ass. But like, you know, yeah. the idea of, I wonder what else is out there. Right.

Let me just try. And it worked out. Yeah, because if there was ever a year to do something new in the political satirical world, it's during an election season. That's generally when new shows of this nature are introduced to the media cycle. So if I have a chance to do something new, this is the window. Because what happened with Trevor, and I write about Trevor in the book, Trevor decided to do something different. different. So I'm like, oh, well, damn, what am I? What am I? What is, what will my story be after this show? None of these jobs are permanent. You lease them. Yeah, that's the truth. How do you

end up with, have I got news for you on CNN? They call me to say, hey, do you want to be on TV again? I go, yeah. There was a degree of hesitancy because it's a panel show. And when you look at the late night satirical news landscape, panel shows generally don't do well in the States. So will this work? And in talking with Mark Thompson over at CNN, who's the head of the network, who's from Britain, and this being a British property, having a real conversation with them about, okay, are you going to give this time to grow and to breathe and find its audience? And they assured us that they would, and they've kept their word. Because so many things, things get canceled after 10 episodes. We're kind of stupid as a country. We need time to learn a

concept and really absorb it and really catch the flow of it. It's a lot of fun, by the way. It's a fake game show presenting current events. We're approaching our 30th episode now. As of the end of 2025, we would have done 30 episodes of this show. That's a beautiful thing. And the ratings are great. It's gaining momentum. We're having more people. wanting to come on, sitting politicians from both sides to the aisle, I want to come on. Yeah. So, yeah. You're feeling all right.

It's feeling all right. What's the next mountain for you to climb? Well, I'm writing a couple of movies. Say more? I can't. A biopic about a revered comedian that has long since left us. Okay. So I'm hoping that the piece is falling in a place to be able to tell that gentleman's story.

I enjoy television. I enjoy acting, but I think movies and just writing more, I'm more interested. Starring in movies? Like, would you be an actor? Bill Burr had a great quote where he said, I don't want to star in anything. I just want to parachute in, kill it, and then leave. Come in and do two episodes, and you never see me again? You can do that.

That's my move. A couple pages. Get out of there. I love that point. So, you know, I would love that. I'm hoping to try and turn this book into something, be it a one-man show, a television show, write some films. One-man show, Roy, please.

I would watch that. We'll see. We need people to buy tickets for it first. How old is your son now? He's nine. So that's a big part of your life too. Yeah, huge. You say in the book, you have to have an open line of communication with your kids.

And that means them critiquing you, too, as a parent. You have to give your kids space to criticize you as a parent. I think letting them feel heard, even if you don't agree, even if you don't comply. even if you don't comply. I think having the one thing my mother and I always had, I always had time to speak my case. You know, before this sentence is laid down before you and your own punishment for two weeks,

what say you about the child? My mom has a law degree. So she was very much, you may speak now, what is your opinion? And I always respected feeling hurt, even if it didn't get the outcome I wanted. Yeah, that stuck with me. Could we do a rapid fire?

Rapid fire. Okay. All right. First joke that killed on stage. Police radio joke about when the police check your license and they look back. And the joke is okay, but me just going to three out, three at one. Yep. Just imitating dispatch. Murder. Who is your invisible audience that you test out material on? Oh, I don't have an invisible audience, but my mom?

you test stuff on your mom? Yeah, I can stress test a premise on my mom, not necessarily the punchline, but the point of view. Hey, I feel like TSA should every now and then just let one person through without checking them. Keep it exciting. Keep the line moving. Then she'll argue and no and ask you, yeah.

Pre-show ritual. Do you have one? No. No. I don't have any pre-show rituals. Post-show rituals. Post-show rituals. Post-show, all of it.

to sit and be alone in the green room for about 20 minutes after and just reflect. Just think. I like stillness. Do you have a hobby outside of all this? Jigsaw puzzles. No way. I love jigsaw puzzles. Jigsaw puzzles. I glue them and frame them. I'll put them on the wall. Cheers to Julesaw puzzles. Best piece of advice you ever got.

My dad used to tell me you're worth more from your neck up than your neck down. You have any advice for someone who wants to do what you're doing? my advice for anybody that's not living in their purpose is to start or find people that are doing what you do or that are driven and just be around them it will rub off the same way negativity rubs off on you same way positivity can yeah thank you so much roywood junior thank you for having me great to have you appreciate that yeah good times this is too good i got it yeah i gotta go back to work yeah me too Thanks, everyone for listening. We hope you enjoyed it. This episode was produced by Zoe Baum, along with Kate Saunders. Our audio engineer is Matt Tierney. Geraldine Coles-Zoccar is our senior producer, and Erica Josephson is our executive producer. Janelle Rodriguez is our executive vice president of programming at NBC News.