Roy Wood, Jr. is a comedian, actor, writer, and host of CNN’s weekly comic round-up, Have I Got News for You. An Emmy-nominated producer of the PBS documentary The Neutral Ground, former correspondent for The Daily Show with Trevor Noah, and 2023 host of the White House Correspondent’s Dinner, he has made a career of drawing on American history to turn a gimlet eye on the American present. His 2017 standup special, Father Figure, tackles the long histories that inform the Black Lives Matter movement and shape Americans across generations. His 2025 special, Lonely Flowers, speaks to the contemporary need for forging connections and the sometimes comic, sometimes devastating consequences of failing to do so.

A product of Birmingham, Alabama’s West End and proud graduate of Florida A&M University, Wood reflects the ethics of care of the communities that nurtured him by supporting nonprofits like the Birmingham literacy programs, STAIR and I See Me, Inc., and touring with the USO. His book, The Man of Many Fathers: Life Lessons Described as a Memoir, comes out in Fall 2025. In June, Adriane Lentz-Smith sat down with the man dubbed by Forbes, “one of comedy’s best journalists” to discuss shared histories, shared premises, and where to find comedy amongst the everyday blues. The conversation has been edited for brevity and clarity.

Would you agree that to be funny about the present, you need some sense of the past? As a corollary, I have a more pointed question about Black pain and how we find comedy amidst a painful past.

I would agree that you have to have a sense of the past because you have got to know where the live wires are. The hardest part about making jokes out of Black history is that so much of this history is raw, and you have to tread around the live wires.

The scholar Craig Werner frequently quotes Ralph Ellison when talking about the blues impulse. He says some folks find a “near tragic, near comic voice” by edging up to the pain and “fingering the jagged grain.” He also talks gospel and jazz, but I think it is in the staring down the wound that the Ellison quote applies to comedy.

For some people it is like that, and I can make comedy for them. But there are people who are very protective about our story, our history. For a lot of folks, it is never going to be anything to laugh about. That’s just what they feel. I don’t worry about those people. I don’t act to offend them, but I do not worry about reaching them.

Even something as simple as me doing a joke about seeing white people work in a Black History museum: that was a true experience based on, I think it was Atlanta at the new civil rights museum when they had just opened it in 2012 or 2013 [Atlanta’s National Center for Civil and Human Rights opened in 2014]. The joke begins, “You have got to respect that. That was a choice,” and it goes on to speculate on the differing relationship to the history that white and Black guides might have. It was just an analysis that struck me as interesting, an observation of what’s better—a Black person or a white person to walk you through Black history. You must have some grasp on what has been to effectively do a joke like that.

I don’t think anybody was better at it than Dick Gregory. When it comes to juggling our pain as a people, I honestly would put Dick Gregory over Richard Pryor. Pryor was a master at taking his pain and weaving and representing it to people as a reflection on society at large, but Dick Gregory would come in kicking down the door about what’s happening around us.

Dick Gregory was very much an activist, and Richard Pryor was not. Gregory’s skill stands out because often I find self-proclaimed activists too pious to be truly funny.

Dick Gregory was an activist who happened to be funny and knew how to flip a joke, but at his core, yeah, he was a straight activist.

To your point, many activists connect to a degree with pain or anger, and I don’t think anger is a substantial vehicle for funny. You can be annoyed: annoyed is a good vehicle for funny. But once you’re plugged into something, and you are angry, in my opinion, you’re less likely to be funny about it. If we’re just talking about what emotion you’re trying to convey or attach the information to. I don’t think anger often works well as a vessel.

Even if you take someone like Paul Mooney. Mooney was ferociously mad with white America, but it didn’t come out in a way that made the joke undigestible. That’s very important: he could almost absorb the anger and redirect it into this thing of collective consciousness with Black people [does a tai chi-esque move], but his anger was throwaway. You would have to talk to comedians that have seen it and audience members that have seen it—but when white people would walk out of his show, Paul Mooney would just tell them to their face, “You can’t handle it. You can’t deal with it. You don’t want to face it.” But then, if there were white people who stayed at the end of the show, there was like a full circle, “Thank you for staying. Thank you for absorbing the message”-type moment. It was serious stuff, and he would add a joke in periodically, but he was never trying to take the edge off of anything he was saying. Neither was Dick Gregory.

Challenging people to stay, to face it, often proves difficult. How do you talk about Black pain in a way that does not reduce the Black experience just to pain? And how do we do so without promoting shame or guilt, just knowing?

We can’t control shame or guilt. That’s just how some people are going to receive the information and respond. I don’t see any solution to that because I don’t believe that we can reasonably tell Black people who are in pain to make sure they care a little bit about how they emote it to other people.

As for guilt, from Michael Brown and Tamir Rice-era activism until now, I think that it would have been naive of us as Black Americans to think that there wouldn’t be some degree of backlash or, “Well, wait a minute. I didn’t enslave you”-type energy eventually coming from white folks. At some point, they were going to break. And they broke, and now you have the backlash—the whitelash, or whatever you want to call it—to all the diversity stuff. “Black fatigue” is a new term: [imitates the voice of the backlash] “We tired of you m***f*** talking about this s***! I’m tired. I’m Black fatigued!” Well, you’re not nearly as tired as we are. Because it’s funny that you’re tired of hearing about it: we’re tired of enduring it, and those are two totally different mindsets. But how do I say this in a way that makes you feel good? Well, maybe it’s not supposed to make you feel good.

I don’t necessarily think that there’s a way to control how someone absorbs this history and its emotionality. I don’t see a way to properly disseminate your pain without undermining and minimizing it. There are probably more or less effective ways, at times, to convey what we need in terms of going forward, and the future, and reparations and stuff like that. However, figuring out the most efficient way to deliver something to a group of people, many of whom reject your pain in the first place, that is hard to do. The comedian Mike Birbiglia says something I quoted often, and that’s, “Jokes only work when people agree on the premise.” The punchline only works if we agree on the premise. Well, in this instance of healing, we both must agree that a wound is there, and there are a lot of people who don’t even agree that Black America has a wound worth treating. So, there’s no proper way to talk to that person, or to make your humanity clear to them. In that case, your humanity has to be seized. It has to be taken.

The question of how to go about doing that is where you find a lot of division amongst Black Americans. I don’t know how we reach any sense of uniformity on messaging to ensure everyone is on board, because then you’re drifting into a conversation about respectability politics.

I often mangle a quote from Audre Lorde who once said that Black people carry shame about the past and white people guilt. Neither is productive and either can be corrosive. I thought about observation a great deal when feeling exasperated with people’s performative crying in the height of Black Lives Matter activity.

My thing with crying white people is that a lot of it is just them processing the horrors of the world for the first time. Most of them came up in a different world, so… it’s a lot. It’s like getting smacked in the face with a bunch of G forces.

Some white guilt that became self-centered, about, “How can I feel better?” And, “Here’s $20.” And “Oh, I gave money to the scholarship thing, or whatever.” Honestly, again, from the Mike Brown to Tamir Rice era till now—a great deal of guilt got commodified. You know, donations to xyz group or to this organization. Many Black groups leveraged that white guilt for money, like, “Hey, you feel bad? Support this cause!” So, for some white people it became about, “Well, here’s some money; I can feel good now. I gave the money. Hey, now it’s up to you. Y’all use the money.”

We, as Black people, have to decide whether or not white people are part of the solution, because they still hold the cards. This idea that we’re going to do it ourselves: walk me through how. Otherwise, I don’t know how much we gain in terms of true equality. To put a finer point on it, if we believe that white American voters are part of the equation for legislating equality—not taking equality but legislating it—then guilt cannot be the only emotion that we exacerbate in white Americans in the hopes of making them change.

We live within capitalism. It is the same way that electric cars didn’t really catch on until they became more efficient. You could have bought an electric car thirty years ago, twenty-five years ago. They had them, but they weren’t efficient. They didn’t look good. They weren’t sleek, it wasn’t affordable. Equality is going to have to be like that. These deportations of immigrants are going to be a very quick exercise in education for a lot of Americans on just how much their racism hurts their capitalism. When you look at Blackness, it’s very much one and the same: you have people denying the truth about how much diversity will make their companies better. All right, cut the programs; let’s see what happens. Maybe you’ll find out that way.

Economic boycotts help, but they do not provide the most efficient way to get people to learn their lessons. Because corporations have bought up so much stuff, to boycott one company effectively, you really need to boycott many. It’s like when some people protested Bud Light for featuring a transgender woman. They were like, “We’re not drinking Bud Light!” Okay, bet. There’s like forty brands bottled and produced by Anheuser-Busch, Big Dog. So you have to quit drinking Bud, Budweiser, those weird non-alcoholic brands: you need a fuuuull list.

You want to talk about a joke adjacent to pain? It never made the Father Figure special, but I had a bit I was working out in the early days in the clubs. When the George Zimmerman trial began, it was alleged that a paper company donated money to his defense fund. And so there was an email. I don’t know if you got it, but there was, like, a super Black email that was getting passed around that basically said, “This is the paper company. Here are all their products. Don’t buy any of these products.” Okay, cool. I clicked the link; and let’s just say the list had forty products produced by this paper company, and of that forty, nineteen were varying styles of toilet tissue. How’m I’ma wipe my ass? Now you’ve done the right in the first part of this email, which is, “Hey, don’t wipe your ass with these toilet papers.” Well, if you’re going to do that, the bottom of the email needs to also be, “Here are alternate ways to wipe your ass.” Because this company, they made a loooot of the brands of toilet paper!

It was just a loose joke about how economic boycotting is sometimes incomplete in its messaging of how to maneuver the problem. But the joke at its core felt too critical of protesting at a time when protesting remained a very important part of the playbook of trying to get laws passed. I did not want to come across like I was undermining, especially as the sentiment was starting to drift into anti-Black-Lives-Matter. If you were a Black person and you spoke remotely against anything that the Left was doing, they could take that one sentence, a quote and blow that thing up, so you had to be very careful about how you spoke.

By comparison, when the Target boycott came out, somebody got the memo because they were like, “Hey, don’t buy from Target.” And then everybody went, “Well, what about the Black people who we love and support who have products in Target?” And then they were like, “Order directly from their website, here were other alternate websites to go to, etc.” The Tabitha Browns and the Melissa Butler Lip Bars of the world, they were telling us other ways to support those brands.

In short, you can be mad at white folks, but if your plan is legislation, cussing them all out ain’t going get the law passed. Now, you don’t have to hug them all. They stand up and cry, fine. “Go ahead and cry. It’s not my place to heal you. Go somewhere, read a book. There’s plenty of them out there, you know, for you to educate yourself.” But I just think that when it comes to oppression and the real horrors of this world, there are a lot of people that are just now opening their eyes and realizing just how interconnected we all are.

As you say, in order for the joke to land, or the message to gain traction, we have to agree on the premise. Yet, we are in a moment when many of the premises that I thought we all agreed on suddenly seem up for debate. How do you craft jokes, particularly jokes rooted in shared knowledge, in such circumstances?

We have to accept the reality that, in our society now, the truth is no longer truth; the truth is what we all collectively agree upon. The only truth is what we, as a society, agree upon. That’s the only truth that exists. Green means go because we’ve all decided that green means go, but someday somebody could decide that green means stop. Then what? I craft my jokes for the people who agree with the premises. If you don’t agree with my premises, my comedy’s not for you. You cannot get everybody. And the pool of who you can reach is becoming more and more separated, based on what your truths are, based on what conspiracies you think are or are not true.

That comes from both sides of the aisle. You know, there’s people who don’t agree with certain things, or “You said, a thing that has rubbed me emotionally raw, so now I’m not going to agree with anything else that you say. I don’t care about any other part of whatever you’re doing simply because of blah.”

The only thing that changes it for me now is that you have to adjust a little bit of the wording of how you shape jokes in the beginning because if you’re not careful, people turn off on the premise. For example, I had a joke that started out with, “You know Elon was right.” And then right there, you’re like, “Whatever.” The worst thing that you think of Elon Musk’s politics, that is what you will assign to that sentence. Whereas, if I say, “But there was one thing Elon did get right,” well, now, you’re going to hold. Because now it’s on me to explain. So you have to play with wording of bits like that because if you don’t, then people turn off, and then they don’t stick with you all the way through anymore. People used to wait for the punch line to be offended, but now they get offended at the premise. Now, if you hit a certain buzzword, you’re not going to let me finish the rest of the joke.

Given how many people reject dynamic understandings of the past—reject both the premises and the validity of informed contestation—can history still matter?

History will continue to matter. We are in a period that we must persevere through, and we will probably spend a generation healing and correcting these wounds. But I don’t think we can ever be in a place where history doesn’t matter, because if you disregard the past, then your future is screwed.

You know, you’re going to say, “This data on global warming doesn’t matter.” Okay, cool. You enjoy the dirty water, because that’s what your grandkids are going to get. We never got to do it, but we had a story that was going around the building at the Daily Show one time about how a lot of developers are buying up property in Miami’s Little Havana and a lot of those developers currently own property on the beach. So the developers believe, essentially, that little Havana is going to be the new beach.

The way we planned to do the joke was as one of those sexy real estate shows. We would talk about how this is new, luxurious beachfront property and have it cut to the drone shot over Little Havana: there’s no ocean. “But in this many years the water will be…” Basically saying that you can disrespect the environment and scientists and data and numbers, but if the folks who have spent millions on buildings are now spending millions somewhere else, there is a reason. And maybe if you won’t believe the scientists, maybe you’ll believe an investor.

But the hard part was getting an investor on the line who would admit it.

Have you ever been to Stone Mountain, the giant granite mountain on the outskirts of Atlanta that has a bas-relief of Jefferson Davis, Robert E. Lee, and Stonewall Jackson carved into it?

I did morning radio in Atlanta for two years, for KISS 104, and in that time, we did one or two radio events out that way. In town, never at the mountain itself. It is not really my thing. I get why a lot of people appreciate it, but [stank face] it’s not somewhere I would ever seek out to go on my own.

The idea of the Confederacy and living underneath the shadow of all of these figures and statues, it strikes me as more of an issue for the people who don’t live near them than the people who do. I’m not saying they aren’t objectionable, but I always find it interesting that the people who live in and amongst that stuff, many of them have made peace with it. It’s not that they accept it, but they just go, “Eh, this ain’t the thing I feel like fighting. I don’t feel like arguing with white folks about Robert E. Lee.” In a lot of ways sometimes I feel like we should have just let them keep those damn Confederate monuments, because then they wouldn’t have been trying to undo our future. There was a hornet’s nest up with the statues which comes at great cost, and it just means more fighting and more to resolve.

I was executive producer on a documentary about Confederate monuments with a wonderful documentarian, CJ Hunt. It’s called The Neutral Ground, and it came out a couple of years ago. The documentary got an Emmy nomination, and it started as an adventure in just looking at the Jefferson Davis Memorial in New Orleans. This before the wave of Confederate monuments started getting taken down, before Charlottesville. But then, as we were out documenting, “Why do people care so much about this old history,” Charlottesville happens. And then it’s like, “Oh, no, you’re trying to erase our past, which means you’re trying to erase our future!” Which seems to me just as irrational as crying, but I get it.

Stone Mountain Park has a laser light show on the side of the mountain. It used to strike me as odd that the crowd would gaze on this ode to the Lost Cause and rebirth spot for the Klan but do so while listening to Pink Floyd in a mostly psychedelic haze. So, yes, the show ends with the Confederates riding off into the sunset, but in the meantime those icons have been engulfed in this festival of silliness.

And, also, Black people go hiking there.

Hiking, and back in my Atlanta days, when you got to the top there was a little film with gnomes! Perhaps there is something hopeful in this, an America where we can stare down our history and not have it limit us—we’re going to climb atop it, devalue the Confederates, and look at some gnomes. And then the light show will come.

Yeah, and that’s it. And it’s perfectly normal. Yeah, perfectly normal.

Speaking of living amidst history, what was your hometown of Birmingham, Alabama like in your childhood? How lively was its historical memory? Its community?

Birmingham was a predominantly Black city. I have said jokingly but seriously that I didn’t meet my first Latino until the seventh grade. I had a Vietnamese classmate in the sixth grade, but Birmingham was predominantly Black and white. I didn’t even meet a Caribbean person until I got to college in Florida. When I say Black and white, it was just southern Black and white. You had a couple of foreign exchange students that were from places in Europe that we did not know and could not pronounce, but they put them all off in the same room. We were in our own little world.

Everything I did was Black, all Black, predominantly Black, mostly Black. Black churches, Black Little League, Black Boys and Girls Club, all Black Boy Scout Troop, predominantly Black schooling every year, except for 6th grade, when I got bused out to the white side of town for a year. Black Mayor. Black barbershops. Birmingham proper was… white flight had come and gone for the most part in the late 1980s to early 1990s, so there were a handful of white people that lived on the West Side. Most were just doing okay. They weren’t balling.

But you know, I just remember it being a bright and vibrant city. It wasn’t like white people pulling up alongside you going, “Hey, boy, where you going.” Now, when you got out in the county, and you got out in the suburbs the predominantly white suburbs, yeah, you’re getting pulled over. I used to deliver pizzas and stuff in high school. I delivered steaks, actually.

Steaks?! Cooked steaks?!

Steaks. Yeah, there was steak delivery in the 1990s. There was a company called Steak-out. And that you just call them, “Bring me a ribeye and a porterhouse.” The same way you call Domino’s for a pizza, you call Steak-out for a steak. Naturally, the only people ordering steaks are people with steak money on a Tuesday night—white people. So I’m in the south suburbs delivering steaks in highfalutin’ neighborhoods, and I’m getting pulled over on the regular because my car is raggedy, and I would never put the big magnet sign on the top of my car because it scratches up the paint. Still, I had to start using it because I kept getting pulled over so much my delivery time was going down. Which meant I had to explain to the customer when I got to them, “I’m sorry I was late. Racism delayed the delivery of your food.”

But you know I always felt safe and calm within the city limits. And I also grew up around a lot of positive Black people who really cared about the neighborhood and the city and the kids in it. That played a big role as well in my feeling supported and also wanting to give back as an adult to the neighborhood. I’m very proud to be from Birmingham, and you know the city was always Black. It was always supportive; it was always uplifting. There’s gangs, sure, but I also walked to the library and did computer classes. I got mentors in strange places and kind people. And I remember the night my father died, strangers came to our house bringing food—people my mom and I had never met. So there’s a community, there really is.

Your dad, Roy Wood Sr., was a pioneering Black journalist who covered freedom struggles in the United States and Africa, as well as Black troops experiences in Vietnam. Did he talk about his work at home?

My dad was a journalist who focused mainly on Black issues. He was the type of guy who would, in a heartbeat, run to whatever drama was going on with Black folks. He covered protests and marches and civil wars. So, by the time he got to Birmingham, you know, he already had the respect of Black people, because he was a key figure in Black media throughout the 1960s and 1970s.

He died when I was 16, so we never got a chance to talk about a lot of what he used to do. I do remember one time he took me to see Jesse Jackson when Jesse was on the campaign trail, and he came through Birmingham, and I was backstage with my dad while he interviewed Jesse at the Boutwell Auditorium. I went with him sometimes on speaking engagements to big mayoral conferences and stuff. To be around my dad was to be around Black men that were moving and shaking.

Most days, I just remember being in the barbershop. The barbershop was this place where city leaders, Black men who ran the city–some above the board some behind closed doors–that’s where they met. They met at Pete Stone’s Style Shop and would just shoot the breeze about this law and that referendum. There would be city councilmen coming in and out of the shop all day, future mayors coming in there, future governors—white men, would come in there from time to time to say, “Hey.” And it wasn’t so much about gladhanding for votes as much as it was just trying to kind of understand what Black people needed and what they were going through. That’s what I remember vividly: the barbershop was very much an epicenter and, by and large, where I learned a great degree of the idea of not only dreaming, but of the idea that you need other people to try and execute those dreams.