On a star-studded Sunday night at the John F. Kennedy Center for the Performing Arts, Conan O’Brien was honored with the prestigious Mark Twain Prize for American Humor. This high-profile event attracted numerous comedy luminaries, including Sarah Silverman, Will Ferrell, David Letterman, and Stephen Colbert. It marked a significant gathering in a venue that has recently been at the center of political turmoil after former President Trump controversially took control of the center, firing board members and appointing himself chairman.

The air was thick with anticipation as many wondered if the evening would serve as a comedic counterpoint to Trump’s administration. The answer was a resounding yes, as the evening unfolded with sharp jabs directed at the former president. Letterman, who presented the award to O’Brien, quipped, “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.” The energy in the room was palpable, filled with laughter and camaraderie as beloved comedians took turns mocking the political climate.

Silverman humorously reminisced about when O’Brien was the only prominent figure with a distinct orange hue, perhaps a cheeky nod to Trump. Colbert added to the hilarity by announcing new board members at the Kennedy Center: none other than Bashar Assad and Skeletor, drawing laughter from the crowd.

O’Brien’s acceptance speech also tackled the elephant in the room. He remarked that Mark Twain had been skeptical of populism, jingoism, and the socio-political climate of his time, which resonated with the audience in the context of today's political landscape. His sly wit echoed his previous approach at other events, where he managed to critique Trump without explicitly naming him. When joking about the best picture winner at the Oscars, he highlighted the triumph of a strong character who stands against Russian influence, subtly linking it back to current global concerns.

The Mark Twain Prize has been awarded since 1998 and is recognized as the highest honor in comedy, with past recipients including icons like Richard Pryor, Dave Chappelle, and Jon Stewart. While the ceremony is primarily a celebration of comedic talent, it often finds its moments of political commentary. Stewart once noted that comedians are often the first target in authoritarian regimes, underscoring the vital role they play in society.

The backdrop of the Kennedy Center has shifted significantly since Trump’s rise to power, with the new board and leadership casting changes on the institution’s future. Many were left wondering about the implications of these shifts on events like the Mark Twain Prize ceremony and the future of free speech in comedy.

Despite the political undertones, the night remained true to its roots: a celebration of creativity and humor. O’Brien paid homage to Deborah Rutter, the former president of the Kennedy Center, who had initially championed him for the award. With a playful remark about modern technology, he joked about losing Wi-Fi, suggesting his acknowledgment of Rutter’s absence due to unexpected delays.

Conan O’Brien has built a career on political humor, from poking fun at impeachment proceedings to his signature style of witty commentary. The night concluded with a promise, as the entire ceremony is set to air as a special on Netflix on May 4, ensuring that the laughter and political commentary will continue to resonate beyond the Kennedy Center.

Indeed, the joke was not only on Trump, but also an empowering reminder of the resilience of comedy—a powerful tool against the tides of political change. O'Brien's night was a testament not only to his comedic genius but also to the enduring spirit of humor in the face of adversity.