Conan’s Big Night, Trump’s Shadow

As Conan O’Brien prepares to receive the Mark Twain Prize for American Humour, the event unfolds amid political turmoil. Weeks after O’Brien was named the honoree, Donald Trump ousted the Kennedy Center’s leadership, installed loyalists, and took over as chairman.

In a social media post announcing the changes, Trump declared that those dismissed “do not share our Vision for a Golden Age in Arts and Culture.” What that vision entails remains uncertain, though Trump has expressed interest in bringing more Broadway productions to the venue and has floated the idea of bestowing Kennedy Center Honors upon Sylvester Stallone and Paul Anka.

O’Brien, who has largely steered clear of overt political commentary throughout his decades-long career, finds himself accepting the honor at a moment when the comedy world — and the broader entertainment industry—wrestles with its stance on the new leadership. The late-night veteran, whose career took off in 1993 when he unexpectedly replaced David Letterman on Late Night, has always leaned into absurdity and self-mockery. Yet he has also engaged with cultural shifts—officiating a same-sex wedding on his show in 2011 was one such moment.

His career, marked by reinvention, has seen highs and lows. He famously lost The Tonight Show in 2010 after NBC controversially reinstated Jay Leno, leading to a dramatic fallout. O’Brien rebounded with a decade-long run on TBS, a thriving podcast, and the critically acclaimed travel series Conan O’Brien Must Go. His recent hosting gig at the Academy Awards was so well received that producers have already tapped him for a return.

Trump’s takeover of the Kennedy Center has led to a wave of responses from artists. Some, including Hamilton producers and actress Issa Rae, have withdrawn from events at the venue. Others, like comedian W. Kamau Bell, have used their performances as a platform to address the controversy.

O’Brien will be honored by top comedians, some likely to address the Kennedy Center’s upheaval. Joining past recipients like Letterman and Chappelle, the ceremony will stream on Netflix later this year.

Reflecting on his career, O’Brien once said, “I was this nobody writer, and suddenly I was told, ‘You’re taking over for David Letterman.’ I thought it was a prank.”

With a career full of twists, Sunday’s event may add another unexpected chapter.