Conan was late-night's longtime underdog. He made it into surrealist art

·8 min read

For the third time in his career, Conan O'Brien left a late-night show Thursday, ending the 11-season run of "Conan" on TBS — preceded by the end of his seven-month stint as the host of "The Tonight Show," and that by the end of 16 years' worth of "Late Night," both on NBC. Unlike those earlier departures, he does not have another talk show on the horizon, at least not on television, but will present what has so far been described only as a "variety show" on HBO Max, a TBS corporate relative.

The final "Conan" was a friendly, appealingly modest affair presented in front of an audience that seemed to include a lot of people who worked on the show and their friends and relations, to judge by the applause accorded various members of the production team in O'Brien's closing remarks. It was taped at Largo at the Coronet Theater, a cozy space long at the center of L.A. comedy; "Conan" has been based there for a year, playing until lately to a crowd of cardboard cutouts and crew members, with O'Brien, his guest and more-than-a-sidekick Andy Richter keeping more than the recommended social distance. The last couple of weeks have introduced live audiences, however, and there has been a lot of sincere, sentimental hugging as the show has lowered its shutters. Even so, it has been a more measured affair than the host's last days at "Late Night," when he took his set apart with an ax.

It was "fitting," said O'Brien, that final guest Jack Black had actually injured himself rehearsing a filmed musical piece in which he was supposed to appear to injure himself; he came onstage with a cane in his hand and a foot in a brace. One waited to see if it were a bit, but it wasn't. "When Carson and Letterman and all these legends go off the air, everything is meticulous," said O'Brien. ("Johnny would have had Jack shot," joked Richter. "That's how they did it then.") Black did manage to rise and sing to the tune of "My Way": "He's tall, he's really pale, he has red hair, like Howdy Doody / But more, much more than this, he did it Cone's way."

Conan's final episodes included visits by Martin Short, J.B. Smoove, Tig Notaro, Patton Oswalt, Mila Kunis and Dana Carvey. Seth Rogen got him to take a hit of a joint he happened to have on him. "I'm like a narc that to prove he was not a narc took some drugs," said O'Brien. "I think it metabolizes and becomes more orange pompadour." Paul Rudd, in a tuxedo, crashed Bill Hader's segment to prank the host once more with a clip of "Mac and Me," the awful "E.T." knockoff he substitutes for whatever film he's supposedly there to promote.

On Thursday, Will Ferrell, who appeared on the last night of O'Brien's "Late Night," Zoomed in to record a packet of farewells for future last shows: "Congratulations on an outstanding run on your HBO Max show; people would say that six episodes isn't a lot, but you packed enough entertainment in them for eight episodes." And, "I'm truly going to miss your Delta flight talk show, 'Wheels Up,' available on select flights from Atlanta to Tampa." O'Brien himself announced "my new career posing as Conan O'Brien on Hollywood Boulevard." An "exit interview" conducted by Homer Simpson with an animated Conan — referencing "Marge vs. the Monorail," an episode O'Brien wrote — opened the show.

Obviously, there is some distance between O'Brien's habitual self-deprecation, whether it expresses genuine feelings and/or supports a joke, and the reality of his success, a trail that leads through the Harvard Lampoon, of which he was president; the writers rooms of "Saturday Night Live" and "The Simpsons"; 28 years of talk shows, which requires being funny night after night; and a highly successful podcast, "Conan O'Brien Needs a Friend," which requires being natural in an unnatural setting. NBC paid him more than $30 million to walk away from "The Tonight Show," which is a rarefied sort of failure, a disappointment stood on the shoulders of great accomplishment.

This self-consciousness is what sets him apart from Jimmy and Jimmy and James and Stephen; they are all more or less regular guys where he is an irregular one; even his whiteness is a different shade of pale. In classic rock terms, it's the difference between being a fan of Neil Young and a fan of those other guys in that supergroup. He is a performer almost by accident, a writer who suddenly found himself — a man who needed much introduction — in David Letterman's "Late Night" chair, shot from a cannon. But that he thinks like a writer must also have influenced the fictional frames his late night shows put around the more or less nonfictional appearances of his guests.

The crazy clubhouses O'Brien and his writers and producers built undoubtedly meant more to the fans than the latest project or hairstyle of whoever happened to be passing through that night. Some characters on O'Brien shows have the flavor of surrealist art or something a child might say to explain what a scribble represents: Sears Tower Wearing Sears Clothing; Chess Piece With a Mullet Riding a Rascal Scooter While Listening to a Ring Tone of “Little Red Corvette”; Hippie Fire Hydrant Riding a Skateboard; Redneck Parking Meter Eating Nachos Out of a Roman Coliseum; Minty, the Candy Cane That Briefly Fell on the Ground.

Though his energy and his looks — Short called him a "a ginger crash-test dummy" — make him hard to place chronologically, O'Brien is 58; he will have been getting AARP mailers for some time now. For late-night-retirement context, he's eight years younger than Johnny Carson was when he quit "The Tonight Show," a decade younger than David Letterman when he left "Late Show," a year younger than Jay Leno when Leno turned the keys to "The Tonight Show" over to him in 2009, before taking them back for another four years. He has stayed in longer than his contemporaries but is getting out sooner than his elders, making sure not to stay too long at the fair.

Probably he would have found the measure of "The Tonight Show" eventually. But perhaps it worked out for the best. O'Brien's self and sensibilities truly are a little strange, a little disturbing, a little bit out of the way. It's not that I would wish less success on anyone, but TBS may have been the better fit in the long run. Bigger is not always better; budget is the mother of invention. In the end, it proved only that there is more to late night than a name or a network. If anything, it was a matter of being struck down only to become more powerful: The imbroglio made O'Brien into a cause, Coco of Team Coco; it gave him an underdog's advantage, set him on the moral high ground and laid the grounds for his future.

Speaking in the Oxford Union (as in university) in February 2020, he explained the decision to cut the show to half an hour and a single guest rather than the old late-night routine of "comedy, first guest that you want to see, second guest that you don't care about, third guest that you don't care about."

The deeper dives, less related to pushing product, are the herald of his mature phrase. (Longer cuts are available online, where Team Coco does most of its work.) O'Brien promised "Late Night" fans he wouldn't "grow up" when he moved to "The Tonight Show," but he's been doing it all along. "Connection," he has often said, is what really matters to him. The "Conan Without Borders" specials, which find him in far-flung locales, acting the genial idiot, willing participant or eager student in cultures not his own, comes out of that desire; the podcast, which goes its own way at length, is its flowering.

"I have devoted all of my adult life, all of it, to pursuing this strange phantom intersection between smart and stupid," he said in the "Conan" finale. "This really crazy and seemingly pointless pursuit to do things that are kind of stupid but have something smart in there somewhere and then there's a little tiny sort of flicker of what is a kind of a magic, I think. That's what I believe. So my advice to anyone watching right now, and it's not easy to do, but try and do what you love with people you love, and if you can manage that it's the definition of heaven on earth."

We cannot all be Conan O'Brian; his talent is rare and, anyway, what an exhausting world that would be. There are good lessons in his life and work for the rest of us, however: You can be strange and still do all right. You can be rejected and humiliated in a public forum and still find people on your side, and go on to succeed in ways you never imagined. You might think little of yourself, but you might be wrong about that.

This story originally appeared in Los Angeles Times.

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