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How Roy Wood Jr. crushed the toughest room in comedy

Backstage with the ‘Daily Show’ comic (and next host?) as he worked on Tucker Carlson jokes and navigated the party scene at White House correspondents’ dinner weekend

Roy Wood Jr. took the stage at Improv comedy club on April 28 to test his material for the White House correspondents’ dinner the following night. (Andre Chung/for The Washington Post)
20 min

It had been a hectic day in Suite 9100 at the Washington Hilton. Roy Wood Jr. and his team of comedians had expanded the Don Lemon section. Slimmed down the reparations joke. And, at the insistence of the writers, inserted a “Vanderpump Rules” reference that Wood still wasn’t quite sure he understood. But now, 2½ hours before the White House correspondents’ dinner, the room was near silent. Wood nervously shuffled his notecards while a barber, can of coloring spray in hand, negotiated just how honest his hairline would be.

“I feel like in a career you get two to three opportunities to skip a level,” he told me as his publicist tried to figure out whether his bow tie was upside down.

The annual week-long party that the nation’s capital throws for itself was another chance for Wood to prove he deserves the permanent host gig at Comedy Central’s “The Daily Show,” where he’s been a correspondent since 2015. When he guest-hosted for a week in early April, he boosted ratings with the help of a surprise appearance by beloved former host Jon Stewart. (A cameo arranged by the executive producer and kept secret from Wood until the day of the show.)

But Paramount executives haven’t hinted at when they might name Trevor Noah’s replacement, and Wood knows he’s too hot right now to sit around waiting. He can’t force them to give him the job. What he can do is kill this set.

“If you’re asked, it’s one of those things that you’ve kind of got to do, bro,” he told me a few weeks after his selection to host the dinner was announced. “The first impulse is, ‘Oh, s---, I shouldn’t have said yes.’ The second thought is, ‘Okay, I’ve just got to prepare.’”

On April 29, 2023, comedian Roy Wood Jr. headlined the White House correspondents' dinner. Here are the highlights. (Video: The Washington Post)

The event is also among the most challenging gigs a comedian can book. It’s held in a stuffy Hilton ballroom where your jokes must compete with clanging silverware, the sounds of room-temperature salmon being chewed, and the occasional clatter of a dropped cocktail glass. You’ve been hired by the media establishment to entertain the media establishment by telling the media establishment that the media establishment is wearing no clothes.

After Hasan Minhaj hosted the dinner in 2017, a stream of reporters approached him at the after-parties to apologize for how coldly his jokes had been received in the room. “One of the things you hear a bunch is, ‘Hey, I know my boss didn’t laugh, but that was really funny,’” he told me.

The self-serious professionals you’re performing for expect to be celebrated more than roasted, and could not know (or care) less about stand-up comedy. “It’s not often that you perform as a comedian in an environment where no one has come for the comedy,” explained Noah, who hosted the dinner last year, and advised Wood on his act. “And number two: It’s not often that you’re in a room where everybody wants you to talk about them but nobody wants you to say anything about them.”

The lines likely to earn laughs and applause from those watching at home are often the precise ones that may lose the room. The ballroom turned on Larry Wilmore in 2016 after he targeted CNN’s Wolf Blitzer. Michelle Wolf, summoned to roast the Trump administration, was run out of town for noting that its chief spokesperson routinely trafficked in untruths. “The audience is the people in the room,” Wood said. “But the words are for the people at home, the jokes are for the people at home.”

As one publicist handed out Altoids and another searched for scissors to open tuxedo jacket pockets, Wood pulled out his phone to blast the Big Tymers’ “Beautiful.” “My life is beau-ti-ful-ah! Livin’ that good life!” he scream-sang as we wove our way downstairs to walk the red carpet and pop into the CBS-Politico pre-party, where Wood leaned in close to media mogul Byron Allen to fact-check a joke. “Both you and Tyler Perry are in the running to buy BET?” the comic asked in a whisper. “We’re up against one another!” Allen made sure to clarify.

Wood had spent most of the day avoiding this type of scene in favor of further refining his routine. But when you’re trying to get a broadcast company to give you the hosting gig of one of its marquee shows, you have to show up at its shindig. “It’s like, do I shake the hands of the top two ranking people at CBS, or do I go prepare?” Wood asked me as we finally worked our way to the exit.

There’s an alternate history in which Wood would have been seated on the other side of the correspondents’ dinner dais. His father, Roy Wood Sr., was a legend — a radio journalist who covered Black soldiers in Vietnam, South African apartheid, and the civil rights movement and was known as the voice of Birmingham, Ala. After high school, Wood Jr. went off to Florida A&M University to study broadcast journalism.

But this was not an attempt to follow in his father’s footsteps. Wood Sr. had 11 children by nine women, was absent for much of Wood Jr.’s childhood, and died of cancer while his comedian son was still in high school. Wood struggled to reconcile the good father he experienced with the horrible husband he saw. His father’s obsession with the news, Wood recalled, was driven by anger at an unjust world. And so he decided whatever he did for a career needed to be about joy.

Then he turned on ESPN and found himself seduced by a young, playful Black anchor who filled his sportscasts with jokes and hip-hop references. Wood already took pride in cracking up his baseball teammates as he sat in the dugout, so he headed off to campus, determined to become the next Stuart Scott.

But midway through his junior year, Wood stole a credit card from the mail at his post office job, then went with some friends to a nearby Dillard’s department store and charged a few hundred dollars of Tommy Hilfiger apparel. He spent a few nights in jail and faced federal felony charges — his public defender told him he was looking at a three- to four-year bid in Club Fed. Never, he learned the hard way, steal mail.

With a few months until sentencing, Wood got on a Greyhound back to Birmingham and showed up at the local comedy club’s open mic night. Being onstage helped him escape the dread of incarceration. For the next four months, he traveled to every comedy club he could find, sleeping in bus stations after the gigs.

Then, to his shock, Wood was given probation. In a second blessing, his probation officer agreed to let him continue traveling for comedy shows as long as he could bring back some sort of documentation — so Wood taught himself graphic design and made posters for open mic nights. He worked the road every Friday through Monday.

By the time he graduated in 2001, Wood had been touring for the better part of three years and still had more than one year left of probation. Some newsrooms told him they couldn’t hire him because of his criminal record. “I’m not here to deny the mistakes that I made,” Wood said, “but they do show me how few people in this country believe in the concept of forgiveness.”

He did get offers from the Tampa Tribune and the Birmingham News, but the $14,000-a-year cub reporter jobs wouldn’t allow travel on weekends. Instead, he took an internship as a morning-show comic at WBHJ 95.7 Jamz — the Birmingham station where his father was once a mainstay — and developed a specialty doing crank phone calls. “He was a genius with it,” recalled Rickey Smiley, the nationally syndicated morning comic who Wood replaced at the station. “I have a morning show now and I play Roy Wood Jr. phone calls, not mine.”

Wood was still coming into his own as a stand-up, openly grappling with how to connect with audiences. For a while, he tried on a cranky persona, playing the guy in the disheveled suit who can’t believe that none of you idiots get it. But the costume never fit. “He has that innocent-looking face,” said Lori Ann “Sommore” Rambough, a comedian and actress who toured with Wood early in his career. “If he came over to your house, as a young girl, your mother would allow him to go up in the room with you. Like, she’d make you guys sandwiches.”

Then, in 2011, Wood was booked to emcee a banquet in Selma, Ala., as part of the annual commemoration of the Bloody Sunday march. The headliner was legendary comic and activist Dick Gregory. When Wood asked the 79-year-old Gregory why he still traveled and performed, Gregory responded that “the fight for freedom is out there. It ain’t at my house.”

For years he’d avoided the heaviness that permeated his father’s work. Now Wood was determined to meld the mission of truth-telling with the joy of joke-telling. His sets became less observational and more political. Today, he occupies the space filled by Chris Rock in the 1990s and Dave Chappelle in the early 2000s — a Black comedian who doubles as one of our most thoughtful political commentators.

It’s a perilous mode to work in, according to comedic legend and Wood mentor Tommy Davidson: Just one joke about a sensitive subject that doesn’t land could be the end of your career. “You don’t get to where he is in comedy without troubleshooting your soul, man,” Davidson said. “It’s just too high of a trapeze act. You fall, there ain’t no f---ing net there.”

Wood likes to structure his jokes as counterintuitive defenses of the seemingly indefensible. And he’s taken to heart the old writer’s trick of jumping directly into the action, ridding his sets of long setups.

“But if we get rid of the Confederate flag, how am I going to know who the dangerous White people are?” is the opening line of his stand-up special “Father Figure.”

“Once you hear … ‘Confederate flag,’” he later explained on comedian Marc Maron’s podcast, “I’ve got your undivided attention.”

Wood began rehearsing about three weeks before the dinner, doing multiple drop-in sets a night at the Comedy Cellar in New York.

He’d quickly decided that the unifying message for his set would be about how political scandal and Washington minutiae distract from the reality that the news media is dying. “There is a bigger dialogue to be had about how when the media suffers, state and local life suffers,” he told me over the phone about two weeks before the dinner. “There’s nobody left to hold people accountable for the stuff that they do, … and that is helping to create inequality in underserved communities.”

“The media this, the media that,” Wood continued. “Your local paper probably has two reporters that have to cover a whole metropolis.”

That was the easiest part. Now for the difficult part: the jokes. You want them to be well written and well rehearsed, but if you craft them too early, the news cycle will make them irrelevant. Long riffs about Chinese spy balloons or sensitive military secrets showing up on video-gamer chatrooms would be too dated by the time of the dinner.

Wood and his writing team, led by former “Daily Show” writer Christiana Mbakwe, began throwing around ideas in a Google Doc and riffing in a group text. Wood figured Senate Minority Leader Mitch McConnell (R-Ky.), who’d recently had a medical incident, should be off limits. The team discussed several jokes about long-shot 2024 presidential candidate Nikki Haley but concluded that there were too many potential land mines in jabbing at a Republican woman of color. He played around with a joke about the affair between former “Good Morning America” co-anchors T.J. Holmes and Amy Robach, but it required too much explanation.

They quickly decided that the audience was too White to make a Lori Harvey joke. And the Black journalists in the room would appreciate a joke about the Shade Room, but there probably wouldn’t be enough Black journalists there for it to be worth it.

Some jokes, of course, are evergreen, so you store away a few: how the Republican Party used to do serious things like bomb children in Iraq, but nowadays, it’s going to war over silly things like books and Bud Light. But still, much of the material has to be tweaked down to the final minute.

As if to prove the point, one week before the dinner came chaos: Fox News prime-time host Tucker Carlson and CNN morning host Don Lemon were suddenly fired on the same day.

“Pretty sure [Wood Jr.] is updating his remarks/roast for the White House Correspondents’ dinner this coming Saturday,” MSNBC host Mehdi Hasan quipped on Twitter. “‘Updating’?” the comic replied. “Man I gotta throw out the whole damn script.”

“To me, this s--- was just a gig bro. ‘Hey, do you want to come do a really scary gig?’ All right, you’re not going to say no,” Wood said softly as we sat in the dark back seat of a Tesla around 11 p.m. on Friday night. “But then you start realizing like, some of the Black folks that are from here, this doesn’t happen, and they don’t get [stuff like this].”

The nation’s capital is several cities in one. There is, of course, Official Washington: the Georgetown aristocrats, the suburban enclaves of the far northwest, and the largely White professional class that populates much of Capitol Hill, Adams Morgan and Shaw, as well as recently created places such as the Wharf, CityCenter and NoMa. Then, of course, there is the District of Columbia: the working-class, majority-Black city full of families, public employees, artists and service-industry workers.

In the gulf between them lives Black Washington: a professional class of reporters, lobbyists, business executives and political operatives who are not fully at home within either scene. Wood spent the night before the dinner in celebration with this city.

His first TV hit after landing around 5 p.m. Friday was with political strategist and television host Symone Sanders, who happens to be his cousin. Later he joined the second annual dinner hosted by CNN’s Abby Phillip and communications executive Lauren Wesley Wilson, then went to the fifth floor of HQ DC House, a Black-owned membership club and event space across from Capital One Arena.

There, Wood emerged from a back elevator with White House press secretary Karine Jean-Pierre and longtime White House correspondent April Ryan and headed directly to the center of the dance floor. When it came time for speeches, he stared down at his shoes as Jean-Pierre detailed his father’s journalism accolades and recounted the story of how Wood Sr. turned down a producer credit on “Soul Train” after fronting Don Cornelius the pilot money.

“My daddy said, ‘Ain’t nobody wanna watch Black people dance for an hour.’ One of the most epic bag fumbles in history!” Wood said once he got ahold of the microphone.

Scores of college classmates at the party were quick to recall Wood as the funny guy who worked at the Golden Corral near campus. “I’ve never experienced anything like this,” Wood exclaimed in wonder as he was mobbed in hugs and backslaps, while a spirited but respectful swag surf broke out in the corner by the DJ booth.

Between selfies, Black journalists whispered suggestions in his ear about ways he could roast their employers. “But if I go onstage and blast these companies in these very specific ways,” Wood turned and said to me, “everyone is going to know who the leaks were!” Ousted CNN anchor Lemon told him not to hold back. Wood warned Lemon that he was going to be the butt of some of the jokes.

Next we were on the way to the DC Improv, the comedy club just south of Dupont Circle, for one last trial run. As we dipped into the main room, two older White men immediately got in a screaming match toward the back. “Yeah, nah,” Wood whispered. “This crowd is too Trumpy.”

While Wood waited to go on the second, smaller stage, his phone pinged with the latest version of the set. A few jokes — one about President Biden not having enough Senate votes to gain approval to take a nap, another about how the various Donald Trump investigations are like different strains of THC edibles — proved to be too complicated for such a short set. The only possible groaner, a joke about school shootings, clearly worked with the improv audience but, Wood reasoned, needed to come later in Saturday’s set, once the audience had grown to trust him a bit. He was still hoping to find space for a quick Dianne Feinstein joke.

“Needs more Tucker,” Norm Aladjem, his manager, remarked once we’d all made it outside of the club.

“Definitely needs more Tucker,” Wood agreed.

About 20 minutes before the start of the dinner, Roy Wood Jr. was in the holding area backstage, not not arguing with his mother. Moments earlier, the two had met and posed for a photo with Vice President Harris, who, sensing the comic’s nerves, reminded Wood that “everything you’ve done has brought you to this moment.” His mother, dressed in an elegant two-tone green dress that she pointedly noted had been charged to her credit card — not his — emerged from the photo line in a visible daze. But now, Joyce Dugan Wood wanted to know why her son hadn’t spent more time with her this weekend.

“She comes on the biggest nights of my career and then wants to know why my schedule is busy. ‘I came to your comedy special taping and you were doing on-camera stuff the whole time!’” Wood said, attempting to draw me into a playful mother-son spat that I wanted no part of. He told his mother they could all go to Cracker Barrel in the morning. She asked whether he was sure he’d be awake on time. He promised he would be. “I just want to know what the plan is,” she shrugged. “I don’t want any surprises in the morning.” Cracker Barrel, Wood insisted.

Before they could resolve further logistics, “Daily Show” producer Matt Negrin came crashing into the circle. “Mike Pompeo is here!” he exclaimed. “An actual fascist. We’ve gotta do a joke.” And so, for the final minutes before dinner, Wood workshopped Pompeo jokes.

As he sat onstage through scholarship and award presentations, the group chat with his writers was a constant stream of updates. Did he see that Bill Barr was there? Did he want to try to tweak the reparations joke? Did he understand “Vanderpump Rules” yet? Wood kept shuffling his notecards. What finally caught his full attention was a stretch of Biden’s speech honoring his father and other pioneers of the Black press. He knew his father could never have imagined an American president forcefully quoting Ida B. Wells in a Washington ballroom.

Now it was showtime. He opened with one of the last jokes added to the set, a riff about Biden leaving a classified document on the lectern. Much of the audience, he said, probably thought he was SNL’s Kenan Thompson. The president, he joked, probably thought he was the dad from “Family Matters.” Drag queens are not trying to groom children, he said to applause. And besides, the children were likely to get killed in a school shooting, anyway. The crowd sighed, according to plan. “Don’t groan, pass legislation!” he replied, prompting more applause.

On the fly, he ditched a Rupert Murdoch joke. (Biden had already made a better one.) He added a new joke about former vice president Mike Pence being really good at hide-and-seek. He didn’t find a spot to roast Feinstein, but he did throw in a McConnell line, health issues be damned. He called Lemon an a--hole. He did not, in the end, joke about Pompeo.

Then, crucially, he landed the heart tug: a soliloquy about the importance of local journalism. He referenced his mother and her work as a campus civil rights activist in the 1960s: Had it not been for the local journalists who covered it, change may never have come.

“Most national stories in this country were at some point first a local story, and those stories are championed by reporters at outlets that, many of them, have now folded,” Wood said as the room broke into rapturous applause. “And if we can’t afford to pay local reporters, then, as a country, we’re only left with that many more blind spots as to where the bull is happening.”

After his performance, Roy Wood Jr. stopped at the CBS party at the French ambassador’s residence for more handshaking and for selfies with Gayle King. Everyone there seemed to have found his set hilarious, even if they had been largely unaware of who he was before the dinner. It was “very, very funny,” former Trump adviser Kellyanne Conway gushed as she clasped the comedian’s hands inside her own.

Then Wood was snatched away. Shari Redstone, the chairwoman of Paramount Global, had arrived on the carpet. He gripped and grinned and posed for a picture.

He got his first drink of the night, a Jack and Coke, and scarfed down some finger food. He’d done what he needed to do, seemingly having met the moment. And now, he was off again — whisked off to the capital of Black Washington, the Smithsonian’s National Museum of African American History and Culture, or to some of us, “The Blacksonian” — to share the stage with Diana Ross.


A previous version of this article gave an incorrect spelling of Norm Aladjem's last name. Also in a previous version, "Daily Show" producer Matt Negrin was misidentified as one of the show's writers. This version has been corrected.