Roy Wood Jr. Is Exactly Where He Wants to Be

Roy Wood Jr.’s new Hulu stand-up special is his best yet. But a lot of viewers may incorrectly believe it’s his first. The 46-year-old comic is well aware of this fact as he speaks on the phone from New York. 

“(My new) comedy special is probably going to be seen by far more people than my first three were on Comedy Central,” he tells me. “That’s not a knock, it’s just the metrics of Hulu and the reach of Hulu globally. My first three specials aired on American-linear television. My first two specials lived on apps that are now defunct (and) were difficult to navigate. So, for a lot of people this, my fourth special, will be their first time meeting me. And that’s huge.”

If Lonely Flowers, which hits Hulu on January 17th, is your introduction to the former Daily Show correspondent’s stand-up, well, you couldn’t ask for a better place to start. His previous Comedy Central specials — 2017’s Father Figure, 2019’s No One Loves You and 2021’s Imperfect Messenger — all had things to recommend them, but this one is the strongest, funniest and most tonally dexterous. 

As its title suggests, Lonely Flowers is built around Wood’s contention that, as a society, we have lost connection with one another. He finds many amusing ways to back up his argument, whether it’s the maddening self-checkout registers at drugstore chains or a hilarious (and unexpectedly touching) story he tells about hiring a photographer who served overseas in the military for several tours and still carries the mental scars. There’s a great bit about being invited to a sex party, and another involving a performer known as “The Bubble Man,” an epic tale that closes Lonely Flowers on a high note. By tracing the many variations of isolation we experience in our technology-driven, late-capitalist culture, he helps viewers feel a little less alone.

Wood has been doing stand-up for decades, but to comedy fans, he’s still probably best known for his years on The Daily Show alongside Trevor Noah or, now, as the host of CNN’s Have I Got News for You, based on the U.K. program of the same name. But Lonely Flowers shows another side of the comic, one less focused on politics and current events as Wood consciously dips his toe into more personal and emotional terrain. As he puts it to me, “This is who I am, this is what I feel. I know I’m the shit — if you don’t agree, go fucking watch somebody else. That’s fine.”

He can back up that bluster: The new special sees Wood flexing his observational skills while embracing getting older and confronting his romantic misadventures. Wood will rattle off a series of jokes, but then get heartfelt for a minute right before he hits you with another killer punchline. He’s in full command, deciding what he’ll reveal about himself and what he won’t. For instance, many are aware that Wood stepped away from The Daily Show in 2023 as Comedy Central took its time deciding who would replace Noah. (A lot of us thought he would have been the perfect next host for the long-running program.) But Lonely Flowers isn’t his platform to settle scores or mock his old employer. In fact, you get a total of one Daily Show joke in the special, which is about Wood looking forward, not back. 

Wood has good reason to have his eyes on the future: As he and I discussed during our hour-long interview, he’s in the midst of writing a memoir and is about to launch another season of Have I Got News for You. Plus, he’s still mulling exactly how he wants to tackle talking on stage about his complicated relationship with his late father, acclaimed civil-rights advocate and journalist Roy Wood Sr., who died when the comic was only 16. Below, Wood gets candid about his career, manhood, revisiting his childhood for his forthcoming book, his Daily Show legacy and what comes next for him.

Lonely Flowers is built around this idea of connection, or lack thereof, that a lot of us feel. When you were developing this material, did you notice that the jokes were naturally all returning to this subject matter? 

It’s how I felt in general. You write material and you perform funny jokes, and then when it’s time to start putting an hour together, you go back and look at what you have in front of you and go, “Okay, well is there a thread here?” You can have jokes and have an hour and that’s fine — I’ve done that before — but then the more I looked at all of this material, the more I started noticing that it was gravitating toward a particular theme. 

Once you decide what this special is “about,” how does that change the hour? Was there a lot of funny stuff that got chucked as a result?

Absolutely. Lost all the political material. I’ve got maybe one half-political joke at the beginning, but I didn’t get into deeper political ideology and laws that need to change — like the way I went in on gun reform and standing for the anthem in (past specials). I have other outlets to do that type of stuff, whereas talking about connection — What are we as a people now? — felt like a fun road to go down, instead of just going, “Joe Biden’s old. Kamala lost.” I have those jokes, but YouTube has shown us that you can have quicker outlets for things that are on-the-nose. I’m having more fun if I’m doing a stand-up show that’s a bit of a dissertation.

In Lonely Flowers, you do a great job playing with tone, segueing from jokes to some really touching moments, in a way you haven’t fully before. It’s not just that you’re staying away from politics — you’re working in a different emotional style.

Playing with the idea of using different emotions as an entry point to get to a punchline definitely intrigued me this go-around. And just seeing what I’d be able to get away with — especially on the road, in the time leading up to doing the actual special, where you’re performing at regular comedy clubs where they’re not really wanting to hear you talk about an in-depth conversation you had with a veteran suffering from PTSD. 

But it really felt like the right thing to play around with this time, just because I haven’t had an opportunity before to really try that. I feel like I’ve earned enough equity. It’s my fourth special, I’ve earned the right to have an unplugged album. (Laughs) Let’s put more emotion in some of these bits. That’s all it is: How much more emotion can I put into some of these jokes? It was fun to also talk a little bit more about myself and my own moments of self-reflection and how I fit into this tapestry of loneliness and social abandonment that we’re all guilty of with one another now.

Early in the special, you peg this loss of connection to the pandemic. Was that how you were feeling at the time, too?

Yeah, I felt a little less connected to people. But the more alarming thing was how comfortable I was with not really talking or interacting with people as much. Then when you start digging at why, you can see the bigger societal issue, which is we’re not even connecting in the casual sense anymore.

Comedy was weird after COVID. Doing the Zoom shows felt detached because you couldn’t feel the energy. A lot of comedians just flat-out refused to do them. There was a big shift in people, just as a whole, (but) what comedians never lost was their ability to be keen observers. We’re still on social media, and one upside of social media for a comedian is that it’s an easy way to see what everybody is going through. It’s like getting to talk to all the crazy people in the food court, all at the same time. 

But, yeah, I definitely wasn’t a fan of Zoom shows. I wasn’t a fan of the audience being 20 feet away — some sort of safety-germ moat. I never did any of the shows where you performed behind the plexiglass. I refused. But the moment you get back on stage (after the pandemic), it’s like riding a bike — it all comes back to you. It’s like coming back to school from a sick day and you get to see all your friends again — only now, you come back and a lot of your friends aren’t well and they’re not as social. That’s us now.

Let’s talk about the story you tell in Lonely Flowers about meeting a photographer who’s a veteran. It has a lot of twists and turns, it’s funny but it’s also sincere and moving. How long did it take on the road to get that story to where it’s really working? 

About a year. But it wasn’t so much the story. Something else that’s happened since COVID is that everyone’s experienced loss on some scale. COVID was the first time I feel like everybody got slapped in the mouth in some regard. It wasn’t like a traditional natural disaster where you have the people in pain and then you have people who feel sorry for them — and then you have the people who aren’t affected, so their life just goes on. With COVID, everybody felt some degree of emotion — you could relate to that. Also, people were more aware about therapy and getting help, so you can talk about something with a bit more depth. 

The difficult part of the material about me hiring this photographer was trying to figure out whether the audience would go with me on a joke where the button of that joke is a fictitious mass shooting. What I figured out was that the more sincere I played the front half of that joke, the darker I was allowed to be on the back half. Because the audience knew my heart, they know I don’t mean what I’m joking about. Having emotion gave me some equity to be a little silly on the back side. 

Look at somebody like Ali Siddiq or Josh Johnson, who I think are two of the best doing it right now. Nobody’s doing funny and emotion better than Ali Siddiq — he’s the best stand-up comic working today. Ali taps into his own emotions, and leans into that, to tell stories. Josh Johnson gets on stage and makes you laugh about something that we’re still raw about collectively — that distance between tragedy plus time, he can close the gap on it. And you’re only able to do that if you’re acknowledging the gravity of what it is you’re talking about.

Being more emotional and sincere on stage, did that make you feel more vulnerable? 

First, you have to be open and honest with yourself in the dark before you can go out on stage and share what you’re thinking with an audience — I try to maintain that relationship with the crowd and not lie. 

The biggest difference in this special is that the first three were very much about the world and what we’ve all observed, where this one is more about what we’re currently experiencing together — and how we can try and get through some of it. I don’t have all the solutions. I do feel like going through this world alone probably isn’t the way to do it.

You have a section in the special where you talk about how hard it is for guys to find new friends in their 40s — basically they’re looking for friends who can replicate the friendships they had when they were much younger and their lives were much different. Did coming to that realization help you in terms of finding new friends?

You learn how to meet people where they are and stop making your friends serve all of your emotional needs. You have to be mindful of that. I definitely went through a period of that. But, like, I’m in a fantasy football league with some guys, and that’s a good outlet — that’s a good place to sit and talk and be in a group chat. But you have to be intentional about connection, the same way you are at cardio.

Recently, you put a clip on YouTube of you talking on stage about modern men struggling with living up to rigid ideas of masculinity. Were you someone who tried to be a tough guy when you were a kid?

I never really tried to. I played sports, I was rough-and-rumble. Didn’t really fight a lot, saw a lot of fights. But I was never teased for being feminine or anything of that nature. 

I don’t think it was until I had my son that I really started getting into any real depth of analysis to what masculinity is — or being able to change the definition of it for him.  That idea “Toughen up, suck it up,” I don’t tell my son that. The more important thing I try to get my son to understand is that there’s a lesson behind anything you’re going through. “Be smart enough to not be angry and not be a meathead and reactionary all the time.” I’m more wired for that than anything else in terms of the types of lessons that I’m trying to pass down to him.

For many viewers, Lonely Flowers will be their introduction to you as a stand-up just because it’s on a bigger platform than your previous specials. How much were you thinking of this special as your first exposure to this new audience?

Yeah, I took that into consideration. That’s part of why I didn’t want to do politics. If you want to know my politics, watch CNN — I have an outlet for it, Have I Got News for You. The difference between that and The Daily Show is that not every stand-up premise works as a Daily Show segment. But for CNN, most of my political stand-up premises can work on that show in some form or fashion. That becomes an easier and quicker outlet to get that stuff out. Politics is changing too fast — the country, the tone of things, it’s moving too fast. But loneliness? That’s been around a while — I think we can sit in this (subject) for a while.

How has Have I Got News for You gone for you? What was the learning curve in terms of hosting that sort of program?

It took time to figure out the show and figure out the joke rhythm of the show. And keep in mind, I’m the host — I’m not there to just joke, I have to keep the conversation moving. I’m a bit of a moderator who occasionally gets to do a quick behind-the-back pass to Amber (Ruffin) or Michael Ian Black. Figuring out the brevity of the jokes, that’s more of a challenge because The Daily Show, as a correspondent, you get to talk for four minutes straight. I’m never talking for more than 10-to-15 seconds at a time, on average, on (this) show. 

We taped (Lonely Flowers) before (the) CNN (show) premiered last fall. I’m introducing myself to the world — I don’t want to just be seen as the political guy. I’ve got three shows coming out that’s not political. I’m writing a book that’s not political. I mean, shit, I was down there with Major League Baseball interviewing retired Negro Leaguers. That’s different stuff, different skill sets.

When you’ve been on other people’s podcasts, they’ll sometimes ask you when you’re gonna start talking about your dad in a significant way in your specials. On Mike Birbiglia’s Working It Out in 2024, you hinted that the material that eventually became Lonely Flowers included some stuff about your dad but it didn’t quite fit. When I watched the special, I was curious if your dad might come up — he doesn’t. 

That was always going to be down the road. I probably started working on (the material that became Lonely Flowers) during the writers’ strike of ‘23. I (thought) about the dad stuff, but that was just too introspective. The more I thought about it, the more I decided that I’d rather talk about that in totality somewhere else — and use this special as an opportunity to explore the concept of emotions and sitting in deeper emotions. The dad stuff will be just as heavy as the photographer’s story — it’ll fill a whole hour, with releases throughout. 

But, no, there was never any considerations of putting any of the dad stuff in this — I just felt like it didn’t go with anything that I was trying to do. Also, it takes the audience down a different emotional journey and a different set of curiosities within their mind. I still wanted something here that left more of a sense of optimism and fun.

Because your peers, like Birbiglia and Neal Brennan, tell you that they want to hear you talk about your dad, is that ever frustrating? Do you ever think, “I’m gonna do it when it feels right, so stop bugging me about it”?

It’s not frustrating because (it comes from) people that I respect whose body of work reflects what it is that I would eventually want to try and do at some point. I’m not going to be rushed, but I get what they’re saying: “You don’t need to wait forever. Stop measuring 12 times and just go ahead and cut the damn piece of wood.” I just know that it’s going to be a lift. 

I figure, while I’m writing this book, that would be the time to (also) write this kind of one-person show or whatever about myself. The book is about lessons I learned from men other than my father — he passed when I was 16. These two (projects) are on the same street, so that’s something that should be ideated at the same time. We’ve got to get through January with the Hulu special. Get CNN back off the ground. Finish the book in February. And then I’ll spend the rest of the year exploring those two things and seeing what I have. 

What has the process been like writing a memoir?

Oh, that’s been quite an emotional journey. You have to re-remember a lot of bad lessons to remember what you learned from them. So, something as simple as flipping through old photos can get you moved a little bit. But you know that you’re writing it, ultimately, (so) there’s something for your son and hopefully other young boys to look at and understand that, number one, your dad’s not going to be the only person to teach you about this world. But, number two, there’s lessons in almost everything — you’ve just got to know where to look.

Looking back, were the lessons you learned as a kid mostly good or bad?

I mean, they’re all great lessons to learn. Some silly, some deep. Something as simple as being kind to a stranger. Learning how to be a good man from watching someone be a bad man. Learning how to choose a spouse from being around someone who had a terrible spouse. Learning not to do drugs — I served drug addicts at a job where I worked in high school. The idea of mental health and dealing with that. 

I’m at an age in this industry where I know a lot of dead comedians — well over 20, knocking on 30. Half of those are suicide and drug overdoses. There’s lessons in those encounters that I’ve had with those people. You have to recount all of that and then put those pieces back together into something that feels like a cohesive story. The book isn’t necessarily funny — I’m sure it’ll be funny in parts, but I’m not writing a comedy book that’s a dump of jokes that never worked on stage for me. That’s not the conceit for the book.

Has it been liberating to write the memoir and think, “This doesn’t have to be funny, I don’t have to come up with a joke here”?

I’m still writing the book — I’m not done. That’s part of the issue — I can’t even answer that completely because I might make another pass and go, “Okay, tonally, how can we juice this up a little bit?” Or maybe it needs to sit in the emotion of it all. 

I’m not out to make a funny book — I just want to tell the stories as they happen, and the humor can come inherently from it. But I haven’t looked at a single story like, “This needs to be funnier.” It’s just, “This needs more detail.” Not all of them are going to be funny — therefore, they’re not all even eligible for a one-person show. And I don’t know if the one-person show is strictly about my dad or if it’s about the people that I met after him. Do I want the one-person show to be funny? Or do I want it to be truthful? The serious-to-funny ratio, I can’t decide until I’ve polished all of the stories and then I look back at the reservoir of content that I have to choose from to put the show together.

Others have mentioned that you might do a one-person show at some point. Watching Lonely Flowers, there are definitely elements of that in the material.

Yeah, I think there’s something that’s deeper than stand-up. I look at Birbiglia. I remember watching Mike Birbiglia in 2004 on a Bob and Tom comedy tour, and while all the other comedians were doing three, four laughs a minute and trying to really just get to the next laugh — like a late-night set — Birbiglia was tactical and calculating. He made that transition away from “traditional” road-comic shit into something that’s much more grand. He’s built an empire off of just being honest (with) emotion, and letting the funny find itself. 

There’s an escalation that awaits me in performance. But how to go about doing that, I’m not going to arrogantly just say, “I’m going to do a one-person show.” I’ve got to figure out how and what it is I want to say first, and then I’ll decide the best way to disseminate those thoughts.

I’m sure many will watch the special waiting for you to dish on your departure from The Daily Show. I love that you reference all that only once, in passing, in such an offhand way — but also in a very funny way.

What happened with me at The Daily Show has nothing to do with the thesis statement of the special. There’s no reason to just get on stage and explain my life since the last time I was on stage — that’s not the type of comedy I do. I don’t talk about myself, for the most part. My third special, I mentioned a story about a friend who’s in prison — I talk about myself in that regard, but I didn’t really delve into that. 

Me making a joke about The Daily Show, we all know it happened, so if you can make a reasonable, quick mention, I think it’s worthy real estate to cover. But there’s no need to live in that because that’s not what I was even wanting to really get into on stage: “Let me tell you what happened and let’s talk about the state of television!” No, that’s not interesting — let’s talk about why self-checkout machines make us want to fight people. 

I don’t have a bunch of kiss-and-tell type jokes. This isn’t like Jamie Foxx — Jamie Foxx has had a far more interesting year than me, we should fully expect his stand-up special to recap what the fuck he’s been through. I’m just a dude who quit a job and got another job — that’s not interesting for me to talk about now. I mean, Chris Rock got slapped on national television, and at best that was, what, eight minutes of his hour? 

I get that, but is there a part of you that loves how many people think, “Man, Roy Wood Jr. would have been an awesome Daily Show host. Comedy Central really screwed up there”?

It's hard to say. Having never hosted the show, in any capacity, and wondering what it could have been with me at the helm — sometimes, it’s a more fun story to wonder what could have been. 

But I’d be lying if I said that the love that I felt from the Daily Show and comedy fans is probably one of the reasons that CNN offered me the gig over there. And I feel very blessed to even have that opportunity. They’re not making a lot of new TV anymore, and most of what they’re making is derivative of old stuff. Since I left The Daily Show, there’s only been two new political, kind of, late-night shows to premiere, and that’s us and After Midnight — and both are based on a preexisting show. So, they’re not doing new stuff. 

I don’t ever want the story of me and The Daily Show to be one of “I got left at the altar.” They were free to choose who they wanted, and they were still deciding at the time that I left. So many people feel like my exit was rooted in pride: “You’re not going to treat me that way.” But I was just thinking about what my future would be after the show. And if I’m going to build something new for myself, I felt like an election year would be the time to do it. So, I don’t have the time to wait for them to decide — I have to leave.

They had a year, and I get it — this is your baby, this is your main moneymaker. It’s your only moneymaker at Comedy Central — (that) and South Park — so you don’t want to fuck up this choice. And at the time, Jon Stewart wasn’t in the conversation — maybe I stay on and be a correspondent with him for a while. Okay, cool, but that wasn’t going to stop the question in my mind, which is, “What’s after this? And when?” If I’m not the host, that question remains in my head — and it’s one that, sooner or later, I would have to answer. 

Man, I’ve been on sitcoms, I got promised another season and then got canceled the next day. I got fired from radio — anything’s possible. So, if you have an opportunity to make a choice that puts you in control of how you move and when you drop out of the plane, I just chose to do that instead. I’m tired of bad news coming out of nowhere.

People say, “Oh, you could have stayed and then maybe they would’ve hired you.” Okay, yeah, I could have stayed — and they could have hired somebody other than Jon Stewart who didn’t want me onboard as a correspondent. Then what? I’m ass out again. That, too, is a possibility. The network was deciding at a time when the company was going through a merger — and you don’t know what’s going to happen on the other side of that merger. I cannot wait — if there is a chance for me to do something better than what I’m currently doing, I have to go and try and create that opportunity now. Because otherwise, you’re doing it two years from now, in the middle of 2027, in a God-knows-what entertainment market. 

I don’t live in some sort of regret or “Glad I did it.” It is just, the way I saw the game at the time, that’s what needed to be done. I did what I believed to be some degree of job security.

You hosted the White House Correspondents’ Dinner in 2023. Because it’s such a unique gig, can you go back and watch it and learn anything from the experience?

I haven’t watched (that) yet. I’ve seen a couple of clips that went around on Instagram that I was tagged in, but to sit and watch it in its entirety again? My nerves cannot take that. The nerves can’t take that emotion. I’ve not watched my Correspondents’ Dinner, and I have not watched my episode of Finding Your Roots. 

The Correspondents’ Dinner, it’s a roller coaster. It’s one of the toughest nights in comedy. I still think the Apollo Theater is tougher, but the Correspondents’ Dinner is definitely Top Two. Once I got the first laugh, before I said good evening, I knew the audience was open to laughing — that was the most important thing, them being open to laughing. At soundcheck, I stashed a bunch of papers in the podium, and then the first joke when Biden leaves the podium is me pulling the papers out. This is at the height of the classified document scandal, and I just turned to Biden and I handed him the papers: “Mr. President, there’s some papers here I need you to take a look at.” 

Once I got that laugh, I felt better. I was like, “Oh, okay, I know what I’m doing, it’s just jokes. Some people are going to like some of them, some people aren’t going to like any of them.”

Some would say, “Oh, but you should go back and watch that so you can work past the difficult emotions associated with such a challenging gig and be proud of what you accomplished.” 

I don’t want to watch it again — it’s like watching me go through danger again. If I did another Correspondents’ Dinner (or) some other event similar, I might go back and watch that. But it’s the only event as a performer where the jokes will only work that day — it’s the freshest and most authentic form of performance. Right up until the day before, you’re still creating this beautiful bouquet of jokes that will only live for 20 minutes. If you did any of those jokes the following week, they would be dead. We were writing Chinese spy balloon jokes two months before the performance — by the time we got there, two months later, it was a drive-by sentence. Things just evolve and constantly change.

In the past, you’ve said you thought you only had three more specials in you. Now that you’ve done Lonely Flowers, does that mean you’ll do two more and that’s it?

Two, maybe three. I don’t know what else there is I really want to talk about. I’ve done enough world analysis. I’ll mine whatever the hell is going on with me internally. Maybe I do a trilogy of dad shit — something on my dad, something on the men that raised me and then something about my son. Just like a trilogy of manhood. 

But I don’t know. I always have random jokes and stand-up that I would do, and that’s fine. But I don’t really know beyond that what interests me right now. Something else interesting enough comes up to talk about, I will. But I don’t know if I just want to spend the rest of my life talking about the issues of the day — on stage at least.

In Lonely Flowers, you argue that people need to be intentional about happiness. How do you do that in your life? And how do you keep that idea from getting too touchy-feely?

You just wake up and go, “Okay, I’m going to take an extra day off.” Or “I’m going to go to see that movie” or “I’m going to go to that play.” I try to be a little more intentional just about small things — watching movies, reading books with my son, stuff like that. And (rather than) trying to be touchy-feely, (I’m) just more just matter-of-fact. It’s just like, “Yo, look, you’ve got to go and do something — this is stressful.” 

(In the special) I don’t think at any point I used the word “depression.” I might’ve said “mental illness,” but I don’t think I did. I think I used the word “sad.” I try not to use words that trigger all of the kumbaya bullshit emotions that an audience will have. That took time to figure out — how to talk about sad shit without the audience being sad, too. Empathy doesn’t help you when you’re performing. The audience, at all times, needs to know that a joke might be coming — and when it does, it’s okay to laugh at it. When you get too touchy-feely, the audience, out of respect to you and your pain, is less inclined to laugh — society would demand that you shut the fuck up and pretend to care.

But the job is still to make people laugh. If you want to make them cry, then go off-Broadway or something. With me, it’s still to make them laugh first — that’s the objective.