Hollywood’s Roast of Trump and Celebration of Conan O’Brien Amid Kennedy Center Shake-Up

The Kennedy Center was buzzing with Hollywood royalty on Sunday night as comedians gathered to honor Conan O’Brien with the prestigious Mark Twain Prize for American Humor. But the evening wasn’t all laughs and applause—many took the opportunity to fire pointed shots at President Donald Trump, who recently shook up the Kennedy Center’s leadership structure in a move that’s left D.C. insiders scratching their heads.

Trump’s decision to remove the Kennedy Center’s leadership in February and appoint himself as the Board Chair has raised eyebrows across the arts world. His new appointees include White House insiders such as Usha Vance, Susie Wiles, and Dan Scavino. If it sounds like an episode of “House of Cards,” well, welcome to 2025.

Comedian Sarah Silverman led the charge, recalling a 2016 appearance on Conan’s TBS show where she played Adolf Hitler in a sketch poking fun at Trump. "They wrote a bit where Conan interviews Hitler, who’s embarrassed to be compared to Donald Trump," Silverman quipped, adding her signature wit: "I miss the days when you were America’s only orange a--hole." Oof—she really went there.

Silverman didn’t stop at historical satire. She brought up a controversial stunt from 2012, where she humorously manipulated an image of Conan’s mouth to resemble female genitalia. "Go ahead and leave those photos on your seat when you go—the guy who took over loves grabbing pussy," she said, referencing Trump’s infamous Access Hollywood tape. Not exactly subtle, but no one ever accused Silverman of pulling punches.

Meanwhile, John Mulaney joined in with his own biting humor, joking that Trump might rename the Kennedy Center after Roy Cohn, the lawyer infamous for his ties to Senator McCarthy and Trump himself. "Next week, this building might be called the Roy Cohn Pavilion for Big, Strong Men Who Love Cats," Mulaney said, proving there’s no better way to fight absurdity than with more absurdity.

Will Ferrell, a prior Mark Twain Prize winner, also took a jab at Trump’s executive order to upend the Department of Education. "I’m supposed to be shutting down the Department of Education right now," Ferrell said. Guess Ferrell’s calendar got a little mixed up.

Host Nikki Glaser summed up the night’s tone perfectly, telling reporters beforehand that ignoring Trump’s shake-up would be "insane." She noted that political tension offers comedians a chance to seize a "rebellious moment," although she admitted that speaking out can come with risks like death threats and doxxing. "It’s an easy laugh but also a chance to say something," Glaser said, keeping her focus on celebrating O’Brien.

For his part, Conan O’Brien kept it classy, thanking the Kennedy Center’s former leadership and paying tribute to Mark Twain himself. "Twain loved America but knew it was deeply flawed," O’Brien said. "Patriotism is supporting your country all of the time and your government when it deserves it." A gentle reminder from the honoree that comedy, like Twain’s, can serve as a mirror to a nation’s contradictions.

The night wasn’t just about politics and barbs, though. It was a celebration of O’Brien’s career and his unique brand of humor, which has earned him a spot among comedy legends like Tina Fey, Dave Chappelle, and Will Ferrell. As O’Brien himself said on the red carpet, his material for next year’s Oscars will depend on the ever-changing landscape of current events. If Sunday night’s ceremony was any indication, the laughs—and the commentary—will keep coming.