Tuesday, October 14, 2025

Conan O’Brien Roasts Trump at Kennedy Center

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Conan O’Brien Receives Mark Twain Prize for American Humor

Introduction to the Event

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.

The Question on Everyone’s Mind

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.

Presenting the Prize

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.”
David Letterman speaking at the Kennedy Center event honoring Conan O’Brien with the Mark Twain Prize for American Humor.
(Clifton Prescod / Netflix)

Jokes andRemarks

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.

Testing the Limits of Comedy

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.

O’Brien’s Acceptance Speech

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.

Previous Appearances and Awards

“‘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.

Politics and the Kennedy Center

Politics are typically not front and center, although it is not unprecedented for the winner to make a loaded comment. When Stewart won in 2023, 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.”
Will Ferrell takes the stage during the Kennedy Center event Sunday.
(Clifton Prescod / Netflix)

Recent Changes at the Kennedy Center

In 2025, politics have become the primary conversation about the Kennedy Center after Trump fired every appointee made 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.

Conclusion

The evening’s proceedings will air as a special May 4 on Netflix. Conan O’Brien’s receipt of the Mark Twain Prize for American Humor was a night filled with jokes, laughter, and subtle yet scathing comments aimed at President Trump. The event served as a testament to the power of comedy in the face of adversity and the importance of free speech.

FAQs

  1. Who received the Mark Twain Prize for American Humor?
    Conan O’Brien received the Mark Twain Prize for American Humor.
  2. Who presented the prize to Conan O’Brien?
    David Letterman presented the prize to Conan O’Brien.
  3. What was the date of the event?
    The event took place on Sunday night.
  4. Where will the evening’s proceedings air?
    The evening’s proceedings will air as a special May 4 on Netflix.
  5. Who was the interim president of the Kennedy Center after Deborah Rutter was fired?
    Ric Grennell was named the center’s interim president after Deborah Rutter was fired.
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