The Comedian Looking for Something All of America Can Laugh At

New York Times

20-02-2025

Partway through his latest special, 'Lonely Flowers,' the comedian Roy Wood Jr. tells the story of the time he accidentally hired a white photographer. Or, as he corrects himself, he hired a photographer who he did not think would be white until he showed up. Whenever he travels to a city for a gig, he explains, artists who live there reach out to him to offer their services. He respects their hustle and sometimes accepts those offers, like the one he got from a guy who wanted to take some pictures of him. 'Come on take the pictures,' Wood wrote back. 'I'll see you next week, Deon!'
Wood drops Deon's name casually, letting the audience pick up on the joke before he has to explain it. As they start to lose it, Wood joins them in astonishment. Pitching his body forward, throwing his arms out and bugging his eyes, he yells: 'You see what I'm saying? I don't know no white Deons either! Never met one!'
Deon ends up being a bald, unimaginably chiseled military veteran with menacing tattoos consisting of 'an animal, a death threat then a Bible verse' decorating his arms, the kind of white man that a Black person might not want to be left alone with. Wood is terrified of him — he makes sure to pay him up front — but he finds him unexpectedly sympathetic. It turns out that after returning from service abroad, Deon feels intensely isolated, and photography gives him a sense of purpose.
Onstage, Wood is unhurried, an amiable man who, despite being 46, has the countenance of a churchgoing grandfather who still starches his Sunday suit. He is a master of the leisurely, even comforting, story that plays to his audience's expectations of what is good, kind and virtuous, only to foil those expectations with a well-timed word or mischievous glance.
When I first watched 'Lonely Flowers,' I could feel this story about Deon teetering toward the saccharine: Maybe we can all get along, or at least get along better, if we just listen to one another. But then Wood lets us in on a disturbing detail: 'I like the camera,' Deon told him, ' 'cause, you know, I get to look down the crosshair and still shoot people.' Wood's look of earnest sympathy dissolves, and we're left wondering how to feel about Deon after all.
Then the joke rounds yet another corner: Wood turns serious again, recalling how sincerely Deon thanked him in the greenroom, shaking his hand firmly and looking him right in the eye. 'I was like, Wooowww,' Wood says, his voice dropping to a stage whisper, seemingly humbled by the interaction. But then we reach the other side of his pause: 'He was about to kill some people.' Wood imagines Deon at home, cleaning his rifle right up to the moment Wood contacts him. 'We'll never know how many lives I saved,' Wood says triumphantly, 'because I took a chance on a white man!'
The story is typical of the special, a civic-minded cri de coeur on social atomization and the degradation of communal life in America, though it's a lot funnier than that makes it sound. Wood's complaint comes from a roguish sensibility that was shaped by his unique artistic trajectory: He got his start on the Black Southern comedy circuit and eventually made his way onto Trevor Noah's iteration of 'The Daily Show,' where he filtered contemporary social issues through his downbeat, absurdist logic.
His humor now straddles those worlds: the bawdy, contrarian style of Black comedy institutions like 'Comic View' and 'Def Comedy Jam,' with its love for life's vulgar, politically murky particulars, and the bien-pensant liberal comedy popularized by 'The Daily Show' and its descendants. Though he became famous for his 'Daily Show' work, the Black vernacular is his bread and butter. You see it in the exaggerated physicality he adopts in the Deon story, the way he thrusts his head out and stares down the audience with an expression reminiscent of Bernie Mac; or in the distinctly Southern phrasing he'll adopt when playing one of his many characters. The cross-pollination yields a brand of comedy whose values are clear but that never loses sight of life's unpredictability. Where so much of contemporary comedy is steeped in certainty, trading jokes for smart points, Wood is interested in the moments that leave us humbled and confused.
With 'Lonely Flowers,' Wood is taking that sensibility to a national audience now mired in a politics of mutually assured destruction. He is wearied but stays firm in the notion that his job isn't to badger and demean the half of the country that disagrees with him. He isn't necessarily hopeful. The special turns on a shouted refrain: 'We ain't gonna make it!' There's an unspoken question at the special's heart, though: In the meantime, as we meander toward whatever it is that awaits us, how are we going to live together?
In person, Wood is funny but sedate, speaking in a deadpan carried along by a prankish undercurrent. Last fall we met in Midtown Manhattan, where he was preparing to tape an episode of 'Have I Got News for You,' a CNN political game show that he hosts alongside the comedians Amber Ruffin and Michael Ian Black. After makeup and a haircut, he ran downstairs for a late lunch before returning to his dressing room, where he strategized with writers about how to introduce the day's guest: the former Republican Illinois congressman Adam Kinzinger. The problem was how to make Kinzinger's career trajectory — following a vote to impeach Donald Trump, he resigned from the House of Representatives in 2021 rather than run for re-election — funny.
'He's the former Republican congressman who once tried …' he muttered before stopping, his voice rising into an exploratory vaudevillian shout. 'Who once voted to impeach Trump. He lost his job, and now he's stuck doing shows like this!' Without pausing, he wondered if it was all right to wade into self-deprecating humor and searched for the precise turn of phrase that might make the audience giggle rather than groan at a political tragedy.
'Have I Got News for You,' an adaptation of a long-running British show, is Wood's first television project since he left 'The Daily Show' in the fall of 2023. As a correspondent, he became beloved for his irreverent takes on the racial politics of the Black Lives Matter era. His set at the 2023 White House Correspondents' Dinner combined an earnest defense of journalists and their profession with piercing humor. (After a joke falls flat, he quips that the reaction doesn't faze him. 'I'm like Mitch McConnell: I ain't got no soul.') The dinner created a groundswell of popular support, with critics and fans casting him as a favorite to succeed Noah on 'The Daily Show.' But as the process dragged on and Comedy Central's intentions remained unclear, Wood was anxious that he would miss the window to have his own show.
Wood was careful in speaking about why he left 'The Daily Show.' 'That is the great inevitability of every job: Sooner or later you leave,' Wood told me. 'Thinking about what's next after eight years was not a premature thought.' If he was going to secure another hosting gig, he decided, he had to make his move before the 2024 presidential election got into full swing.
Wood isn't one to let an opportunity slip through his fingers. 'I ain't from the land of dreams,' he told me this past fall. He was raised in Memphis, Tenn., and Birmingham, Ala., and his father was Roy Wood Sr., a radio-journalism pioneer who reported on Black platoons in Vietnam, South African apartheid and the civil rights movement for the Black Chicago radio station WVON before helping found the National Black Network, the first Black-owned radio news service, where he was the news director. His mother, Joyce Dugan, was a respected teacher. Though his parents were highly regarded in the community, Wood's childhood was sometimes shaped by a sense of scarcity and limitation. 'We were raised by people who were fortunate to be able to vote, to drink from the same water fountain,' Wood said. 'They were so exhausted from that battle that all they wanted was a house and a fair wage. The idea of dreaming beyond that was not commonplace, and in a lot of instances it was frowned upon. In the South, you dare to dream beyond the horizon.'
His father's work presented one model for how Wood might dare to dream. When he enrolled at Florida A&M University in 1996, he decided he wanted to work in broadcast journalism, a major that required he take classes in public speaking. He discovered that every time he spoke in front of his classmates, he got laughs without even trying. Wood liked the feeling those laughs gave him, and he started studying the acts of comedians like Adele Givens, Sinbad, Chris Rock and D.L. Hughley. George Carlin, he says, was canon for the fearlessness of his topics and concision with which he expressed opinions that audiences might otherwise find outré. 'I used to listen to 'You Are All Diseased' once a week, listening to the wordplay and the inflections. It was just perfect. Then I would immediately throw on some Master P.'
In 1998, Wood was arrested after buying clothing with stolen credit cards and was suspended indefinitely from Florida A&M. This youthful indiscretion yielded an unexpected blessing: Wood still received the financial aid he would have used for his tuition, and that money — along with a job as a server at the buffet restaurant Golden Corral in Tallahassee — bankrolled his fledgling comedy career. He took buses across the South, sleeping in bus stations between gigs. When he returned to Birmingham to perform at an open mic at the Stardome, one of his mother's students saw him and told her about it. She was infuriated and insisted that he focus on getting back in school. Wood eventually did, and even graduated, but he didn't quit stand-up. Instead he drove out — in a car his mother bought — to cities like Charlotte, sleeping in the passenger seat when he had to. Sometimes, when venues canceled on him, he would take day-labor jobs on construction sites to pay for gas.
Wood's style was molded by the difficulty of finding his voice in Black clubs across the South. His own middle-class experience of Blackness wasn't necessarily aligned with his audience's, and his early jokes — routines about the annoyance of a roommate's eating your food, for example — didn't always land. Working those rooms taught him how to craft observational humor in a way that would resonate for everyone from older Black professionals to gang members. But he also learned not to talk down to people. 'A Black audience will go with you anywhere on any journey,' he said, 'if you make it funny.' He learned to embrace his off-kilter humor without condescending. 'That's what I know about,' he said. 'I don't know about selling weed. That's not my experience, and my job as a comedian is to present to you my experience. And mine is a weird one.'
Eventually he found himself in front of increasingly diverse audiences, too. 'One night I'm performing for drug dealers, the next night I'm performing for coal miners in eastern Kentucky — what are the unifiers?' he recalled. His task, as he saw it, was to find the joke that would make both groups laugh. One of his best jokes from those days, he told me, was about being pulled over by the police and figuring out whether or not you're going to jail based on how long it takes for an officer to get back to you after he runs your ID. It was a perfect bit, he said, because it could unify the room. 'White people got friends that go to jail!' he said. 'Especially rednecks. Poor white people deal with the same stuff that Black people do.'
Wood's focus on social issues was a natural outgrowth of that comedic approach, which he hones to perfection in 'Lonely Flowers.' Early on, he riffs on the absurdity of shopping at stores where it's impossible to find someone who works there. 'Only time you see an employee at the grocery store is when you do self-checkout wrong,' he jokes before launching into a chorus of voices: the checkout machine telling you that you made a mistake, the tottering and elderly employee overseeing the checkout stations, the grocery-store cashiers who provide some of the only social interaction for lonely and unstable people. This morphs into a bit about pharmacies where everything is under lock and key and you have to fend off other customers after you find an employee to unlock all the merchandise. 'When you find an employee in the store, you got to hold they hand,' he says, holding a phantom hand, strutting, warning off phantom rival suitors with a possessive stare.
Wood's critique — the way technology has left us prone to dysfunctional loneliness — is trenchant, but his approach is fundamentally goofy. There's a strange way, too, in which the goofiness reinforces the melancholy at the heart of his joke, a yearning for an entire range of interactions that have fallen to the wayside in a world that doesn't have use for them.
When I called Wood in late January, he was midway through a mini-tour through Wyoming, Colorado and Oklahoma, driving to six Air Force bases in nine days. Before that, he attended the premiere of 'Love, Brooklyn,' in which he has a supporting role, at the Sundance Film Festival in Park City, Utah. A few days after the mini-tour, he would visit his alma mater in Tallahassee and continue to New York to begin the new season of 'Have I Got News for You.' I wondered why a comedian of his stature would submit himself to such a grueling run.
'It feels familiar, it keeps me grounded,' he told me. Those trips reminded him of his early life on the road, when he would perform at the Comedy Zone in Ozark, a small town near an Army base in southern Alabama. Those days put him in touch with the profound weirdness of America. In Ozark, he said, 'the town is troops and foreigners. Wherever you got deployed, you came home with a wife of that race, so it's one of the most diverse cities in Alabama — Asians and Indians and Arabs, and they all sound like they're from Alabama because they came over here, didn't speak English, and the English that they learned was Alabama English.' From Ozark, he would move on to audiences of college students at Fort Walton Beach, Fla., and retirees in Biloxi, Miss. 'And then Tuesday I'm in Atlanta at Uptown with Earthquake and Nard Holston' — two popular Black comics — 'and a couple strippers in the club, booing me.'
Contemporary comedy, he said, doesn't necessitate that kind of encounter. Social media, podcasting and platforms like YouTube have changed the landscape, allowing comedians to target audiences that will be most responsive to their humor and make substantial money doing it. In a world where you can earn half a million dollars off a podcast, he said, why would you go to Ozark for $150? For him, though, refining his act in front of all sorts of audiences grounds him in a specific ethos.
'I spent the first decade of my career meeting Americans where they were, figuring out what was important to them and figuring out how to make those things funny,' he told me. 'Every armpit, every factory town, every we-used-to-make-something-here city — I've done it. So you start realizing that a lot of people are all individuals, and to a degree most are harmless.' People are only dangerous, he believes, when they allow their selfishness and ideological rigidity to blind them to the suffering of others. His touring feels like a shield against that selfishness, an investment in a connection with his fellow Americans.