It finally happened. On March 23, 2025, the Kennedy Center handed over that bronze bust of Samuel Clemens to the man who once spent a decade being chased by a Masturbating Bear. Seeing Conan O'Brien Mark Twain Prize winner status become official felt like a long-overdue glitch in the matrix being corrected.
Honestly, it’s about time.
Conan has been the "comedian's comedian" for forty years. He’s the guy who survived the messiest late-night divorce in history and came out the other side with a podcast empire and a travel show that makes people actually like Americans again. But this wasn't just another trophy for the shelf. The ceremony at the Kennedy Center was weird, political, and deeply emotional.
The Night Everything Got Weird (In a Good Way)
Most of these award shows are stiff. You get the montage, the polite applause, and a few jokes about how old everyone is. But when you’re talking about the Conan O'Brien Mark Twain Prize gala, "stiff" isn't in the vocabulary.
Adam Sandler was there. So was Stephen Colbert, John Mulaney, and even David Letterman—who looked, by his own admission, more like the current state of Mark Twain’s corpse than anyone else in the room.
The vibe was different.
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There was this palpable tension in the air because of the political climate in early 2025. Comedy felt like it was under a microscope. Triumph the Insult Comic Dog showed up, obviously, and immediately insulted the entire audience for even being there. John Mulaney joked about the Kennedy Center being renamed after Roy Cohn. It was a night of "the resistance" gathering together, as Letterman put it, to celebrate a guy who has always used his brain as a weapon of mass distraction.
Why Conan actually deserves this
A lot of people think Conan is just the "silly guy." They remember the red pompadour and the string dance. But if you dig into his history—Harvard Lampoon president, The Simpsons writer (he wrote the "Marge vs. the Monorail" episode, for crying out loud), and the architect of a specific kind of smart-stupid humor—you realize he’s the closest thing we have to Twain.
Twain wasn’t just a guy who wrote about riverboats. He was a biting satirist who hated bullies.
In his acceptance speech, Conan really leaned into that. He pointed out that Twain "punched up, not down." He talked about how humor is a way to handle the "glorious mess of being human." It wasn't just a funny speech; it was a defense of why comedy matters when the world feels like it’s falling apart.
The Will Forte Moment and the Dancing Twains
You can't have a Conan event without some level of absolute absurdity.
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Toward the end of the night, Will Forte appeared in the audience dressed as Mark Twain. They didn't just exchange a few lines; they bickered, they reconciled, and then they slow-danced. Then, a whole chorus of Mark Twain impersonators came out and started dancing with each other.
It was peak Conan.
High-brow intellectualism meeting low-brow physical comedy. It’s that specific intersection where he lives. Most people would be afraid to look that ridiculous while receiving "the highest honor in comedy." Conan? He lives for it. He finished the night playing "Rockin' in the Free World" on guitar with Adam Sandler. It was loud, it was messy, and it was perfect.
The Netflix Factor
If you missed the live stream, the whole thing hit Netflix on May 4, 2025. It’s worth a watch just to see Reggie Watts get genuinely choked up talking about how Conan gave him a shot when nobody else would. That’s the thing people forget—the Conan O'Brien Mark Twain Prize wasn't just about the laughs. It was about his reputation as a "team player."
Comics like Nikki Glaser and Kumail Nanjiani showed up because Conan is famously one of the few people in Hollywood who actually helps other people without expecting a kickback.
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What the Mark Twain Prize actually means for his legacy
Some might say an award doesn't change anything. Conan is already wealthy, famous, and has a dedicated fanbase of "Chill Chums." But the Conan O'Brien Mark Twain Prize cements him in a very specific lineage. He’s now alongside Richard Pryor, George Carlin, and Tina Fey.
It validates the idea that you can be "the silly guy" and still be one of the most important voices in American culture.
He didn't have to become a "serious" commentator to get respect. He didn't have to stop doing voices or making fun of his own pale skin. He just had to keep being the fastest, smartest person in the room for four decades.
Twain famously said, "Against the assault of laughter, nothing can stand."
Conan has been proving that true since his days at NBC, through the TBS years, and now in his podcasting era. He’s shown that you can lose your dream job and still win the game. He's shown that being "nice" isn't a weakness in comedy—it’s actually what keeps you relevant when everyone else burns out.
If you want to really understand the impact of this moment, do these three things:
- Watch the acceptance speech: Skip the clips and watch the full 15-minute speech on Netflix or YouTube. It’s a masterclass in how to be humble and hilarious at the same time.
- Revisit the "Monorail" episode: Remind yourself that the guy who was slow-dancing with Will Forte also wrote what is arguably the greatest 22 minutes of television history.
- Listen to the "Conan O'Brien Needs a Friend" episode with Mike Sweeney: They go behind the scenes of the ceremony and talk about the bits that didn't make the final cut (like Bill Hader’s segment getting trimmed).
The prize is a bronze bust, but the real reward is the fact that Conan is still here, still weird, and still the guy we turn to when everything else feels a bit too heavy.