Conan O’Brien Understands Himself Better Than Anyone

Conan O’Brien’s peak moment of triumph at the Academy Awards earlier this month followed one of his spicier jokes. “Anora uses the F-word 479 times,” the late-night veteran and first-time Oscar host said of the eventual Best Picture winner. “That’s three more than the record set by Karla Sofía Gascón’s publicist.” It was a roundabout way to reference the elephant in the room—the disgraced Emilia Pérez star’s social-media troubles. As the attendees gasped with shock and delight, O’Brien performed a jaunty variation on his “string dance,” a lanky jog-in-place motion accompanied by a resplendent grin; I smiled in recognition of the looseness. “I’m having fun,” he declared right afterward, and he meant it: He sealed his command of the show at that instant, and was successful enough that he’s already been hired to host the ceremony again next year.

The most notable part of this gag was not the joke itself, a standard late-night quip delivered with appropriate piquancy. What made it stand out was that O’Brien sold the line the same way he always has, since he began his on-screen television career in 1993: with joyful abandon. And his Oscars flex felt especially meaningful ahead of another upcoming career highlight: O’Brien is this year’s recipient of the Mark Twain Prize for American Humor (an honor handed to a comedy luminary every year by the Kennedy Center, at least for now). But he’s not receiving the award as a gold watch to recognize his semiretirement from television. No, 32 years after the premiere of his first talk show, and four after his last one drew to a close, O’Brien has become the rare performer whose success relies upon his consistency—even if that means he’s still whipping out the same old string dance.

A sense of defiance has long been baked into O’Brien’s signature move. Lorne Michaels, the creator of Saturday Night Live and the man most single-handedly responsible for O’Brien’s stardom, supposedly hated it. The journalist Susan Morrison’s recent biography of Michaels recounts how O’Brien ignored the note from his mentor (and Late Night producer), shrugging off Michaels’s suggestion that he lose one of his more whimsical flourishes. Instead, the host’s mesmerizing lift of the hips went on to punctuate his monologues over the years, to the approval of his audience. Going against someone like Michaels is a risky move for any comedian to make—but O’Brien’s career has been defined by his steadfast commitment to the bit, no matter how unusual or even off-putting. His mantra as a performer seems to be: If he finds it funny, someone else will. It’s an uncommon purpose in the business of comedy, and even more uncommon to stick with for as long as he has. But O’Brien understands himself better than anyone.

[Read: Conan O’Brien understood the assignment]

The comedian’s staunch love for the goofiest non sequiturs means he’s guaranteed to use them on even the most prestigious stage. During the Oscars broadcast, I was most elated at the gags that felt like they had sprung from O’Brien’s Late Night set decades prior—like a giant puppet of a sandworm from Dune playing “Chopsticks” on the piano. These were the instances of elaborate silliness he might have devised as a lowly comedy writer, before he’d ever been shoved in front of a camera; they fit just as well into his routine today.

O’Brien’s elevation from behind-the-scenes comedy nerd of choice (on SNL and The Simpsons) remains an improbable showbiz occurrence—one that he still litigates every chance he gets. It’s a regular conversation topic on his chat podcast, Conan O’Brien Needs a Friend, which has become another hugely successful evolution in his broadcast career: When he’s speaking to practically any of his comedy peers, O’Brien still marvels at the divine kismet that led him to where he is now. He remains nostalgic about how he got the chance to succeed David Letterman as the host of NBC’s Late Night; he’s similarly never forgotten the scars of his first year on the job, when the reviews were scathing, the viewership numbers were shaky, and his contract was being renewed on a week-to-week basis.

Shouldn’t he be over all of that? After all, O’Brien has proved any doubters wrong repeatedly, through every peak and valley. Late Night went from being dependent on precarious renewals to a nightly powerhouse; he became a comedy figurehead at the cable channel TBS and, later, the streaming service Max, where he stars in a continuing series of travel documentaries that are essentially paid vacations. But it’s still easy to understand his never-ending agitation. Even after a decade-plus of O’Brien proving that his brand of absurdism worked with the mainstream, NBC couldn’t quite believe it; the network removed him as the host of The Tonight Show, a role he’d assumed in 2009, after just seven months. It was a short-lived stint that ended in an infamous blaze of glory, a final week of live shows full of his favorite recurring sketches, which doubled as a sort of Viking funeral for his dream job.

[Read: Conan O’Brien keeps it old-school]

O’Brien followed that debacle by launching a new late-night program on TBS—simply titled Conan—and has since wound things down a little more gracefully. He’s taken on slower projects, like his podcast; chat shows have become forgettable vanity projects for many celebrities, but O’Brien’s genuine, consistently funny take is an elite example of the form. The host has referred to the journalist Robert Caro as one of his favorite podcast guests—a more traditional interview than is typical for the show, staged between an ardent fan and his intellectual idol. But one of the show’s most viral clips is much more representative: The veteran SNL writer Jim Downey pretends to have never heard about Jeffrey Epstein’s misdeeds, to O’Brien’s bleating objections. The moment captures the tension in O’Brien’s humor, which mixes his natural affability with an impulsive streak; he manages to walk the line of faux outrage without alienating his guest or audience.

Since launching in 2018, Conan O’Brien Needs a Friend has become so successful that the host has received some credit from industry analysts for the podcast boom that followed. Through it all, little about O’Brien’s approach to comedy has changed—listen to a monologue from 1993, 2003, or 2013, and compare it with his opening routine at this year’s Oscars. The only thing that’s really different is what he’s joking about.

That’s not to call O’Brien or his work stale—it’s more that the comedian has always managed to shape the current media moment around his own established persona. While his Late Night forerunner Letterman was probably the comedic polestar of Generation X—gruff, cynical, and biting the hand that fed—O’Brien became a bedrock influence for the next generation of Millennial comics. His mix of silly surrealism with an old-timey flair and knowing respect for the entertainment of yesteryear spoke to a generation caught in between digital eras: O’Brien could devise an extended Music Man parody on The Simpsons, and also wheel out a costumed character known as the Masturbating Bear or pull a lever that triggered Walker, Texas Ranger clips to play on Late Night. The characters and concepts he gravitated toward bordered on childish, but his progressively more dedicated fans would come to anticipate these zany touches with glee.

[Read: Long live the delightfully dumb comedy]

I sometimes wonder if the door is starting to close on O’Brien’s comic perspective as he grows older and broadcast formats shift. But he’s dependably found a way to fit it into new comedic spaces as needed, time and again. Early in his tenure on TBS, he launched a segment called “Clueless Gamer,” in which his producer Aaron Bleyaert tried to teach him how to play video games; each installment descends into a frustrated O’Brien lobbing a litany of insults at both the television and his co-host. What was clearly invented as an internet-friendly aside quickly became a popular series unto its own—even though O’Brien’s attempt at engaging with a younger generation’s interest was loaded with scorn. Or perhaps that’s why it was so compelling: “Clueless Gamer” distills O’Brien’s masterful use of his idiosyncrasies, and his ability to apply his point of view to the most dissonant of situations.

Similarly, O’Brien’s frenzied guest spot on the popular YouTube interview series Hot Ones in April 2024 endeared him to a new audience. He deliberately underlined his advanced age (at least, compared with Sean Evans, the show’s 30-something anchor) and brought a “doctor” along to support him as he devoured spicy chicken wings. Melding his particular style with the show’s sensibility, he produced a moment that was outrageous and scripted in a manner that no other guest had attempted. Critics have called his appearance the best episode in Hot Ones’ history, and the viral social-media boost it gave O’Brien likely helped him secure the Oscars gig months later. It’s difficult to imagine the dignitaries who preceded him—talk-show legends such as Johnny Carson and Letterman, or even Jay Leno—lowering themselves to that kind of madcap spectacle, or even engaging with such an unfamiliar type of comedic broadcasting. O’Brien tackles these frontiers with relish, but without sacrificing his core identity.

In her book, Morrison writes that Michaels first alighted on O’Brien as a possible new Late Night host because of his humor pedigree. Prior to his time on The Simpsons and SNL, O’Brien had served as the president of the esteemed Harvard Lampoon. His perceived classiness perhaps clashed uncomfortably with his silly string dancing for Michaels, but that duality has been the secret sauce of O’Brien’s success all these years. His is a sort of erudite buffoonery that consistently tap-dances between clever, self-aware, and patently stupid. He’ll eat your hot wings, or play your video games, or host the Oscars, and even while he’s doing a terrific job of it, he’ll act like the wheels are coming off the bus. More than 30 years after he first debuted on television, O’Brien still seems to be nervously glancing over his shoulder—always making sure he’s not leaving his true self, or anyone else, behind.

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