Conan O’Brien’s Kennedy Center Mark Twain Prize ceremony best and worst moments

Conan O’Brien is the recipient of the John F. Kennedy Center for the Performing Arts’ 26th Mark Twain Prize for American Humor, following in the recent footsteps of Kevin Hart, Adam Sandler, and Jon Stewart.

The ceremony (on Netflix Sunday) took place on March 23 during a precarious moment for the national cultural center. Just months earlier President Donald Trump was appointed chair of the D.C. institution’s board and cleaned house, replacing longtime board members with his own loyalists, while others resigned in protest. O’Brien’s honor was one of the most significant events to take place since the upheaval and some wondered if it would take place at all.

It did, and Entertainment Weekly was in the room for it. The night was filled with many highlights, from Kumail Nanjiani giving a brilliant Ted Talk spoof, to Stephen Colbert invoking O’Bren’s recent viral moment on Hot Ones, to the honoree himself flexing his comparative literature muscles.

Read on for the best and worst moments from the Kennedy Center’s feting of Conan O’Brien.

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WORST: The new normal

From an enhanced security presence to a subdued red carpet, the recent firing of the director of the Kennedy Center and purge of the board of directors cast an unfortunate shadow over the typically joyous proceedings. (The few stars to engage media before the show included stand-ups like Bill Burr and Nikki Glaser, who are adept at thinking on their feet and skirting questions around the controversy.) Several participants throughout the night chillingly alluded to whether this might be the final Mark Twain prize ceremony – period. Then again…

BEST: Onstage Trump material

The show itself mined the current situation to often hilarious ends. Will Ferrell joked he’s been busy shutting down the Department of Education, while recurring Conan character the Interrupter credentialed himself as a cabinet secretary overseeing the Department of Housing and Urban Development. Colbert suggested Bashar al-Assad and Skeletor were also in the administration. And Sarah Silverman said she missed the days when O’Brien was “America’s only orange a–hole.” Direct references to the president were mostly avoided but the presenters were, in the words of David Letterman the “most entertaining gathering of the resistance.”

WORST: Pretapes

Fred Armisen appeared in video bumpers portraying people from O’Brien’s past – Harvard’s dean of students, his agent, his therapist – that were framed to introduce clips of the honoree throughout his career. The problem? The actual moments with Armisen simply weren’t necessary and distracted from the greatest hits.

Martin Short and Bill Hader (not Steve Martin?) also appeared in a filmed segment that mostly fell flat.

BEST: Familiar Faces from ‘Late Night’

After the Max Weinberg 7 warmed up the crowd, the show itself brought back many friendly faces from Late Night With Conan O’Brien, such as the Masturbating Bear and Triumph the Insult Dog, who emceed the event. Mouth cutout fake interviews with the likes of Bill Clinton even returned, as did O’Brien’s beloved sidekick Andy Richter. Ultimately, several of these characters joined the Interrupter to present the Mark Twain Prize to the awardee, in a wonderfully surreal full circle moment.

WORST: Wasted opportunities

Two of O’Brien’s best talk show moments were bungled at the ceremony. The first is the classic recurring Mac & Me clip, randomly introduced by Paul Rudd at the tail-end of Richter’s appearance. Usually the randomness of the clip is the point – however Rudd was not in attendance, and its appearance lacked the feeling of spontaneity of previous incarnations. It was just shoehorned.

More concerning, legendary Conan guest, the late Norm MacDonald, only appears in a brief video – and there’s no showcase for his iconic appearance alongside Courtney Thorne Smith. For those unaware, this was during the press run for Carrot Top’s doomed “box office poison” Chairman of the Board, which MacDonald improvised was spelled B-O-R-E-D. It is a hall of fame talk show moment and was a constant fixture online when clips on eBaum’s World and YouTube first started going viral. It deserved its own segment the way Glaser spotlighted an O’Brien-favorite Walker, Texas Ranger clip. MacDonald, who has his own playlist on the comedian’s own YouTube account, deserved more.

BEST: Heartfelt origin stories

Several presenters honored the impact O’Brien’s comedy had on them growing up. John Mulaney described how invested he has been in the comedy legend’s wild career trajectory throughout his own life and career journey. Nanjiani recalled watching Late Night as a young, lonely college freshman from Pakistan living in Iowa. And Reggie Watts movingly noted O’Brien’s fundamental decency and grace as a person, getting emotional.

WORST: Gross-out humor

This is not exactly ‘bad’ but cringe-worthy moments — including Glaser joking about her dad’s sex tape and Silverman taping a picture of O’Brien’s mouth underneath the audience’s seats to resemble a certain part of the female anatomy — seemed out of place at the Mark Twain ceremony.

BEST: Jay Leno digs

While O’Brien was too classy to drudge up his sordid Tonight Show history with fellow Mark Twain prize honoree Jay Leno, other presenters took digs, including Colbert, who lamented retired late night hosts who fill their golden years with a “heartbreaking number of cars.”

BEST: The grand finale!

After being introduced by Letterman in a true moment of late night TV history, O’Brien made a moving case for comedy in the Trump era, and enunciated a thoughtful and pointed perspective on Mark Twain’s resonance in today’s world. People may overlook this from his bio, but O’Brien majored in history and literature and his senior thesis at Harvard was on the works of William Faulkner and Flannery O’Connor. So, when he takes a few minutes to describe how Twain’s comedy celebrates national fears and attacks hypocrisy and jingoism, he is not speaking lightly.

Twain, noted O’Brien, hated bullies and populism and always punched up, attacking American self-importance. Again, while Trump was not the direct target, O’Brien’s point was not lost. Previously, some people wondered whether it was appropriate for the comedian to even participate in the awards, given the pressures around the Kennedy Center. This speech was a necessary answer to that. It was brilliant and struck the exact right tone.

On sillier fronts, O’Brien also thanked folks from his career via a professional livestock auctioneer. And the show ended with a fantastic rendition of Neil Young’s “Rockin’ in the Free World” that perfectly encapsulated the comedian’s ethos – shredding on guitar alongside Adam Sandler, a mob of Mark Twain impersonators (including Will Forte) joining them on stage. It was joyful and ridiculous, even hopeful.

Conan O’Brien: The Kennedy Center Mark Twain Prize for American Humor special is streaming now on Netflix.

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