“You’re the court jester for the king,” Larry Wilmore says of his gig cracking jokes before the president at Saturday’s White House Correspondents’ Association dinner. (Peter Yang/Comedy Central)

“Keep it 100,” says Larry Wilmore, the comedian and talk show host, repeating the catchphrase that has become his trademark and guiding principle. Be honest, he means, keep it real and true — no matter what anyone else thinks.

So on Saturday night, when Wilmore is the featured act at the White House Correspondents’ Association dinner, seated on a dais with President Obama and Washington’s media elite, how is he going to approach this?

“You’re court jester for the king,” Wilmore says. But the king should expect to be skewered.

Fifteen months into his stewardship of Comedy Central’s “Nightly Show With Larry Wilmore,” the comic has fine-tuned a strain of commentary that seems a perfect match for this moment — the close of Obama’s presidency amid both a burgeoning movement for the sanctity of black life and a presidential campaign electrified by racial politics.

As Comedy Central comedian Larry Wilmore prepares to host the 2016 White House correspondents' dinner, here's a look back at his jokes about President Obama over the past eight years. (Nicki DeMarco/The Washington Post)

Like Obama, Wilmore is 54 years old and African American, with a daughter heading to college this fall. He made a name for himself in Hollywood writing rooms in the 1990s, but it wasn’t until he went before the cameras as “senior black correspondent” on Jon Stewart’s “Daily Show,” deconstructing the black political and socioeconomic situation in America, that he made his name as a performer. As Stewart ended his long run as host of the satirical news show last year, he backed Wilmore for a late-night Comedy Central slot and suggested that the new show focus on marginalized voices and issues of race, gender and class.

Wilmore’s nightly monologue often takes a tone of exasperation. He sets forth his point of view on the 2016 campaign in a regular segment called “The Unblackening,” a.k.a. “the quest to de-Negro-fy the White House.” That, he says, is what conservatives really mean by “take our country back.”

“America went black and they decided to go back,” Wilmore jokes by phone from New York. “They had a different opinion than what we always thought.”


Shenaz Treasury, Sen. Cory Booker, Bill Burr and Talib Kweli were guests on Wilmore’s “Nightly Show” debut in January 2015. (Stephen Lovekin/Getty Images for Comedy Central)

Bernie Sanders made his fourth appearance on Wilmore’s show in April 2016. (Paul Zimmerman/Getty Images for Comedy Central)

He recently interviewed a half-dozen black Donald Trump supporters (key talking point: “What the f--- are you thinking?”). When Hillary Clinton surrogate Madeleine K. Albright declared that “there’s a special place in hell for women who don’t support other women,” Wilmore put up a photo of Monica Lewinsky and asked why women didn’t have a certain young intern’s back during that scandal. He’s invited candidates onto the show for “soul food sit-downs” over fried chicken and cornbread. (Bernie Sanders took him up on the offer.)

Still, Wilmore, who is on the political left, calls it the “irony of ironies” that his ascension in late-night comedy comes amid a crushing wave of stories about young African Americans charging police brutality.

“It’s both a curse and a curse,” he says. “The curse is that the stuff is happening, and the curse is that you have to try to find humor in it.”

He took his show to Baltimore last year following the death of Freddie Gray, who died while in police custody. There, Wilmore ate pie with members of rival gangs to discuss a truce they called during the upheaval that followed Gray’s death. There were few light moments in that conversation.

“One of the things I talked to Jon Stewart about was that we felt there should be a conversation about these things, especially from a comedic point of view, [but] it’s not the easiest way to do a comedy show.”

Wilmore started in comedy with observational humor about his own experience. One early riff: “I would always get asked, ‘Are you mixed with something?’ because I’m light-skinned. I’d say, ‘If I was a beer, I’d be Negro light, and I’d be a third less angry.’ ”

That got laughs, and Wilmore continued to develop his cerebral act, including an imitation of the Rev. Jesse L. Jackson that reliably killed with audiences. But his nerdy shtick fell out of favor in the Def Comedy Jam era of the 1990s. He left stand-up and got a job writing for Keenen Ivory Wayans on the sketch show “In Living Color.”

The show “brought hip-hop culture into American living rooms, the brashness and style — not just comedy,” says Wilmore, who still laughs aloud at the memory of characters such as Homey D. Clown, a grumpy ex-con forced to work as a children’s entertainer as part of his prison work-release program (“Homey don’t play that”).

“It was material you didn’t see that much in television at the time,” he says.

Wilmore also wrote for “The Fresh Prince of Bel-Air” and “The Jamie Foxx Show.” He created and executive produced “The Bernie Mac Show,” for which he won an Emmy. With Eddie Murphy and Steve Tompkins, he created the 1999-2001 animated series “The PJs,” which he likens to a black version of “The Simpsons,” set in an inner-city housing project.


“It’s a curse and a curse,” Wilmore says of doing a current-events comedy show at a time of so much dire news in the country. (Peter Yang/Comedy Central)

“The show was a class comedy and largely about the inequities that happen to people of color in this world, and Larry reveled in the satire and the commentary on the disenfranchisement and the inequities in society,” says Tony Krantz, the studio executive who backed the program.

One of its characters was a crack addict known as Smokey, whom Wilmore thought of as a descendant of Jim, the spaced-out druggie on the ’70s sitcom “Taxi.” “He’d say things like: ‘I got to go. Crack don’t smoke itself,’ ” says Wilmore, shifting into Smokey’s raspy voice. Those kinds of lines got Wilmore an invitation to meet with the NAACP, which took offense at the show, but he pushed back. “I wanted the right to be offensive,” he told C-SPAN a few years ago. “We can make fun of ourselves. . . . I don’t want to be the noble Negro all the time.”

“He was one of the few show-runners for whom I worked that I had to remind myself that he was the boss because he was so cool, so soft-spoken,” says Shawn Michael Howard, the actor who voiced Smokey in “The PJs.”

Wilmore has tried to maintain a family atmosphere on his late-night show. It’s become a close-knit team, an important thing for Wilmore, who moved crosscountry last year and went through a split with his wife. They have two daughters.

“There’s always something in show business,” he says of his personal life. “At the outset you get something great like a show, but it can be tough.”

His show is still rebuilding its audience, which drifted from that time slot after previous host Stephen Colbert decamped to CBS. But Viacom brass have signaled their long-term support of both Wilmore and Trevor Noah, who took over Stewart’s show last year.

What sort of jokes does he have in store for the first black president? Does Larry Wilmore believe Barack Obama has kept it 100?

“You and I both know that the president cannot keep it 100,” Wilmore says, laughing. “The real question is: How close to 100 did he keep? I’d say in the beginning he kept it about 60. He has gotten blacker and blacker in the last four years. He’s been at about 80. Obama don’t care. That’s what we talk about around here. He doesn’t care what you think. All the executive orders he’s issued. At this point, he’s decided to take matters into his own hands.”