Conan O’Brien received the Mark Twain Prize for American Humor on Sunday night at the John F. Kennedy Center for the Performing Arts, drawing Sarah Silverman, Will Ferrell, David Letterman and Stephen Colbert to the center’s most high-profile event since President Trump staged a hostile takeover of the place in mid-February, firing board members and declaring himself chairman.
In the days leading up to O’Brien’s big night, a tantalizing question loomed large: With that many funny people packed into one of the most contested spaces in the country, will the joke be on Trump?
The answer — as pointed jokes at the president’s expense volleyed across the historic room, now a front line of the culture war — was an unequivocal yes.
When Letterman presented the prize to O’Brien at the end of the night, he said, “I’m not a historian, but I believe that history will show, in history for all time, this will have been the most entertaining gathering of the resistance, ever.”
And at another point Silverman said to O’Brien, “I just really miss the days when you were America’s only orange … ” — finishing the sentence with a colorful word for the exit point of the human digestive system.
Colbert joked that the Kennedy Center had announced two new board members: Bashar Assad, the ousted president of Syria, and Skeletor, the Mattel character known as the Evil Lord of Destruction.
The evening was a test for comedy, decorum, free speech and what kind of comedic high jinks the new Trump-appointed administration of the Washington center would tolerate. Jokes abounded about whether the night’s festivities would be the last for the storied award — considered the comedy world’s top prize. Previous honorees have included Dave Chappelle, Adam Sandler, Letterman, Bill Murray, Kevin Hart and prominent Trump critic Jon Stewart.
Kennedy Center watchers who wondered if O’Brien would address the Republican elephant in the room during his acceptance speech got their answer when the comedian made this jab: “Twain was suspicious of populism, jingoism, imperialism, the money-obsessed mania of the Gilded Age and any expression of mindless American might or self-importance.”
O’Brien’s indirect but scathing comments about Trump echoed his approach as host of the Academy Awards this month, where he lobbed his Trump zinger without speaking the president’s name.
“‘Anora’ is having a good night, that’s great news, two wins already,” O’Brien said, referring to Sean Baker’s eventual best picture winner about a fiery sex worker who marries a capricious young Russian oligarch — and resists a campaign of intimidation and domination by her new in-laws. “I guess Americans are excited to see someone finally stand up to a powerful Russian.”
The Mark Twain prize was conceived of in 1997 as comedy’s answer to the Oscars and Grammys, and Richard Pryor received the inaugural award in 1998. The ceremony is typically a funny, feel-good love fest — with comedians who care about other comedians handing out the big award. Jerry Seinfeld celebrated Julia Louis-Dreyfus when she won in 2018; O’Brien was there to roast his friend Sandler in 2023.
For the record:
1:01 p.m. March 24, 2025Jon Stewart won the Mark Twain Prize in 2022, not 2023, as previously stated.
Politics are typically not front and center, although it is not unprecedented for the winner to make a loaded comment. When Stewart won in 2022, he said: “Comedy doesn’t change the world. We’re the banana peel in the coal mine. When a society is under threat, comedians are the ones who get sent away first. It’s just a reminder to people that democracy isn’t the threat. Authoritarians are the threat to comedy, to art, to music, to thought, to poetry, to progress, to all those things.”
In 2025, politics have become the primary conversation about the Kennedy Center after Trump fired every person appointed by former President Biden. The new board installed Trump as chairman and named his ally Ric Grennell as the center’s interim president after firing longtime President Deborah Rutter.
It was Rutter who lauded O’Brien’s selection for the Mark Twain prize when it was first announced in January. In a statement she called the late-night host and globe-trotting comedian “a master of invention and reinvention, consistently pushing the envelope in search of new comedic heights.”
O’Brien respectfully tipped his hat to Rutter during the ceremony, saying, “My thanks to the people who invited me here, several months ago: David Rubenstein and Deborah Rutter. I don’t know why they aren’t here tonight. I lost Wi-Fi in January. I’m guessing they’re in traffic.”
O’Brien is no stranger to the Trump joke. In 2018, when he was hosting his eponymous talk show on TBS, he made fun of Trump for not watching his own impeachment hearings.
“Today the new evidence against President Trump was called ‘damning,’ and some say this could end his presidency,” O’Brien said during his opening monologue, before acting flustered and saying, “No, wait, that joke was from two years ago.”
After getting a round of applause, O’Brien kept riffing in his signature having-too-much-fun-despite-himself style.
“That joke is also from one year ago, and six months ago,” he said. “We’ve used that cue card, like, 15 times.”
The evening’s proceedings will air as a special May 4 on Netflix.
The Associated Press contributed to this report.
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