On Sunday, Conan O’Brien stepped into the spotlight at the John F. Kennedy Center for the Performing Arts to accept the Mark Twain Prize for lifetime achievement in comedy. But this wasn’t just a celebration of his 30-year career—it was a defiant, joyous send-off in the face of uncertainty swirling around the iconic venue.

At 61, O’Brien became the 26th recipient of this prestigious award, a moment that should’ve been pure triumph. Yet, the mood was bittersweet. Just weeks before, in mid-January, President Donald Trump turned the Kennedy Center upside down, ousting longtime president Deborah Rutter and board chairman David Rubenstein. In a swift power move, he replaced the board with loyalists and crowned himself chairman. The shake-up left staffers and artists reeling, wondering what’s next for a cultural cornerstone.

O’Brien didn’t shy away from the tension. With his signature wit, he honored the night’s namesake, Mark Twain, a man who “hated bullies” and “punched up, not down.” “Twain loved America, but he knew it was deeply flawed,” O’Brien told the crowd, his words landing with extra weight in today’s fractured climate. He gave a heartfelt shoutout to Rubenstein, Rutter, and the Kennedy Center staff—“worried about what the future might bring”—earning a roaring ovation that felt like a collective exhale.

A Night of Laughter and Defiance

The evening buzzed with an undercurrent of unease, and the comics on hand didn’t hold back. On the red carpet, Nikki Glaser nailed it: “It’d be insane not to address the elephant in the room. This night is about Conan, but it can be both.” Inside, the tributes to O’Brien were laced with jabs at the new regime. Stephen Colbert deadpanned that the Kennedy Center’s new board members included “Bashar Assad and Skeletor.” John Mulaney predicted the venue would soon be rechristened “the Roy Cohn Pavilion.” Sarah Silverman? She let loose with Trump zingers too spicy to repeat here.

Then came the grand finale—a moment so absurdly Conan it could only be his. A Mark Twain impersonator popped up from the audience, sparking a playful debate with O’Brien. Next thing you know, they’re slow-dancing on stage. The scene escalated when a dozen more Twain lookalikes and past recipient Adam Sandler crashed the party, belting out Neil Young’s “Rockin’ in the Free World.” It was chaotic, glorious, and the perfect cap to a night that refused to bow quietly.

Conan: The Goofy Genius Who Keeps Rising

If anyone could turn turmoil into triumph, it’s Conan O’Brien. He’s never been the political firebrand type—his comedy leans toward silliness and self-deprecation. But he’s not afraid to get real when it counts. Back in 2011, he made waves by officiating a gay wedding live on his show, uniting his costume designer Scott Cronick and partner David Gorshein in a heartfelt moment.

O’Brien’s journey is the stuff of legend. In 1993, he went from a behind-the-scenes writer for Saturday Night Live and The Simpsons to replacing David Letterman on Late Night—despite zero hosting cred. He thrived there for 16 years, outlasting every predecessor. Then came the messy Tonight Show chapter: tapped to succeed Jay Leno in 2009, he lasted just seven months before NBC yanked him for Leno’s return. The fallout was ugly, public, and ended with a hefty payout for O’Brien and his team to walk away.

But Conan doesn’t stay down. He bounced back with a TBS talk show, killer podcasts, and the hit travel series Conan O’Brien Must Go, now gearing up for season two. His recent Oscars hosting gig was such a smash that he’s already booked for next year. Elder statesman? Sure. Done? Not a chance.

The Kennedy Center’s Uncertain Future

Trump’s vision for the center remains hazy. He’s bragged on social media about ushering in a “Golden Age in Arts and Culture,” tossing out ideas like more Broadway shows and Kennedy Center Honors for Sylvester Stallone and Paul Anka. Meanwhile, artists are pushing back. Hamilton producers and Issa Rae have canceled gigs in protest. Others, like W. Kamau Bell and cellist Erin Murphy Snedecor, have taken the stage to call out the changes—Snedecor even closed a recent set with Woody Guthrie’s “All You Fascists Bound to Lose.”

A Legacy Worth Celebrating

O’Brien joins a stellar lineup of Mark Twain Prize winners: Letterman, Leno, George Carlin, Whoopi Goldberg, Bob Newhart, Carol Burnett, Bill Murray, Dave Chappelle. Sunday’s ceremony, streaming on Netflix May 4, was a reminder of why he belongs in that pantheon—and why nights like this matter, even when the ground feels shaky.

In a world of bullies and chaos, Conan O’Brien stood tall, danced with Twain, and rocked the free world. That’s a legacy worth laughing about.