Conan O’Brien Breaks Free, Changing What Life After Late Night Can Look Like

After hosting talk shows for nearly three decades, Conan O’Brien has come to believe that longevity is overrated. The first time he made this point to me was in April at a restaurant in New York, when he proposed that all statues and monuments should be made with durable soap that dissolves in seven years. A month later, in his Los Angeles office, down the hall from his podcast studio, he declared himself anti-graveyard.

Asked if this means he wants to be cremated, O’Brien responded, “I want to be left in a ditch and found by a jogger.” Taking up space in a cemetery seems selfish to him. “I say this in a positive way,” he added, shifting to a less jokey tone. “We don’t matter.”

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Since leaving late-night television in 2021, O’Brien, 61, has become more reflective about life (and death), given to philosophical flights of fancy that he compulsively alternates with comic tangents. He champions the intersection between smart and stupid, but in conversation, what stands out is how quickly he moves between light and heavy. In one of several interviews, I asked him if he was happier now than when he was on television and his response was to question happiness itself. “At best it’s a fleeting moment after a rainstorm when the sun’s coming out,” he said. “Being contented comes in little moments, here and there.”

The only thing trickier than being a late-night talk-show host is being a former one. Some relapse (Jon Stewart). A few vanish (Johnny Carson, Craig Kilborn). Most enter a more modest era (David Letterman, Jay Leno). Since he started writing for “Saturday Night Live” in the 1980s, O’Brien has built one of the most consequential comedy careers. His late-night tenure is beloved by comedy nerds, helping define a sensibility for a generation of comedians like Bill Hader, Eric André and Nikki Glaser. His postshow work may turn out to be more impressive.

It helps that his brand of joyfully goofy absurdity ages well. Stewart may have beaten him out for Emmys in the George W. Bush years, but jokes about the Iraq War have a shorter shelf life than the masturbating bear, a recurring character on O’Brien’s late-night show that is exactly what it sounds like. His reputation has grown as new generations have discovered his work online.

The other reason O’Brien has done well since leaving “Conan,” his final late-night show (after “Late Night” and “The Tonight Show”), is that he’s always been excited by experimentation. “I enjoyed playing with that form,” he said of the talk show. “The stuff I’m really interested in, there’s so many opportunities to do it now. ‘Hot Ones’ is proof.”

O’Brien appeared on “Hot Ones,” an online show in which the host and guest talk while sampling increasingly spicy sauces, the same week in April that he returned to “The Tonight Show” for the first time since 2010. There was a time when O’Brien believed that happiness looked like hosting “The Tonight Show.” Then he got the job.

The mess that followed, the final salvos in the late-night war of long ago, led to his losing his time slot, quitting after less than a year and sinking into a depression. But it also cured him of the notion that any talk-show job is the answer to his problems and taught him how to rebuild a bustling career, which he is now doing again.

Going back to his old show would have once been a very big deal. And it was, to O’Brien. “I did it for me,” he told me days later, before stopping to explain that he was careful to not dig into that past because people have real problems and he merely had “showbiz problems.” Still, one of the few questions he would not answer on the record was whether he would reconcile with Leno.

THE MOST REVEALING ASPECT of O’Brien’s return might have been that it was overshadowed by “Hot Ones.” For 30 minutes, O’Brien made every other episode look bland, hijacking the interview, adopting a swaggering idiot persona, hilariously taunting the host and swigging entire bottles of hot sauce while becoming increasingly unhinged. There was a clownishness and commitment that is hard to imagine any other late-night host pulling off. This half-hour earned more than 10 million views and sparked an impromptu retrospective of his career, with comedy bits from decades ago circulating on social media. “Conan O’Brien” trended for days.

“Many of my friends went online and thought I died,” he said. The contrast between the muted response to him on “The Tonight Show” and the lovefest generated by “Hot Ones” was not lost on O’Brien. It says volumes about the way culture works in 2024 (online virality matters more than a network spot), but also about his new renaissance.

Stephen Colbert, who, of the current late-night hosts, is closest to O’Brien, argued that part of his friend’s late-night legacy was expanding the limits of silliness in the form. (“All rubber chicken, no knife” is how Colbert sums him up in an interview.) O’Brien is doing the same thing for a travel show. Every episode of “Conan O’Brien Must Go” (which has been picked up by Max for a second season), includes an early shot of him floating down a river in Thailand holding a rubber chicken. He plays the buffoon, mocked by people in each country he ventures to.

For a late-night host, O’Brien was early to podcasting. His show, “Conan O’Brien Needs a Friend,” which he sold to SiriusXM for a staggering $150 million, set a template for other retired hosts like James Corden and Trevor Noah. The podcast started while he was hosting, and after leaving, it kept him regularly in the culture.

His career hasn’t shifted course so much as been broken down and reconstituted. His new projects reflect a change in how he sees his own gifts, “a huge dividing line” in his life. Since he was a kid, O’Brien was an anxious, self-flagellating overthinker. His older brother Luke recalls the plates and silverware of their table rattling because Conan’s leg was always shaking from “tons of subterranean energy churning” inside of him.

As a kid, Conan O’Brien even confessed to his father a concern about his tendency to worry. “My father, who I love, once said that if you agonize enough — he used the word ‘agonize,’ I’ll never forget — if you agonize long enough, eventually ideas will come.”

If his early career was a screenplay, this was its inciting incident. O’Brien told me this story twice, both times emphasizing “agonize” as if the word held a talismanic power. It motivated him to get into Harvard, apply the same intensity to comedy and get early jobs at “SNL” and “The Simpsons.”

His unlikely talk-show career, initiated when Lorne Michaels plucked him from obscurity to take over for Letterman at “Late Night,” began with a joke that seems to hint at his teeth-grinding personality: a cold open in which he walked through New York carefree while everyone, from girls playing hopscotch to a talking horse, reminds him that he’s under a lot of pressure and that he “better be as good as Letterman.” It’s a comic nightmare of his inner monologue that ends with him considering killing himself.

MANY COMEDIANS SEE a connection between misery and their ability to be funny, often citing humor as a survival mechanism. But after considerable therapy and reflection, he has come to believe that so much stress didn’t help him be funnier. “Looking back now, I think some of my best ideas came from just goofing around,” he said.

He points to possibly his most celebrated writing credit: the monorail episode of “The Simpsons.” He describes its origins in an Olympic Boulevard billboard for a monorail, leading him to write on a legal pad: “Springfield gets a monorail. Homer likes the idea. Marge not so sure. First act: ‘Music Man.’ Second: Irwin Allen parody.” He brought this pitch to the “Simpsons” office, writers liked it and started adding jokes. “It was like falling off a log,” he said. No agonizing at all.

The podcast shares that seeming effortlessness. Freewheeling and improvisational, it features longer, more searching conversations. And his Max travel series shares qualities with the sketch work and man-on-the-street comedy from his talk shows, applying his surreal and parodic energies to rambling scenes that leave him freedom to play.

These new projects don’t have live audiences and come closer to the O’Brien who cracks jokes in writers’ rooms, going on what he calls “runs.” Ask friends about his funniest moments and they say how hilarious he is behind closed doors in free-form conversation. Capturing that version of O’Brien on television was the “white whale,” said Robert Smigel, who started with O’Brien on “Late Night” and wrote with him on “SNL.”

In a Zoom interview, Smigel said O’Brien could “free associate in a way that was funnier” than all but a handful of “SNL” veterans like Adam McKay, Jim Downey and Bill Murray. Colbert calls him “pound for pound the funniest person to just sit down with, with the possible exception of Dana Carvey” and marvels at his joke-per-minute rate.

O’Brien prefers funny scenarios to jokes. “People say: ‘Do you miss late night?’” O’Brien said, as if the question missed the point. “I had 30 years before late night where I was doing the same things.”

In May, at a taping of his podcast in Los Angeles, O’Brien walked onstage to a standing ovation. He poked fun at the opera seats in the theater, played straight man in a sketch, bantered with two sidekicks, interviewed John C. Reilly, talked to audience members and played guitar with his band. Backstage, O’Brien sounded giddy. “I love the freedom of this,” he said, adding, “It’s just me, authentically me, for better or worse.”

A band member interrupted to tell O’Brien about a musical his daughter was in. O’Brien is so recognizable, approachable and, because of his height, conspicuous, this happens a lot. When a fan approached at a restaurant in April, he immediately invented a very funny scene in which I was his accountant and he was getting an audit. In this case, he introduced me to the musician as a New York Times critic, then shifted into a performance as my editor enraged that instead of a Conan O’Brien profile, I was returning with a review of a musical adaptation of “Charlie and the Chocolate Factory.”

O’Brien is remarkably quick. When he starts riffing, it’s a marvel to behold. But his playful tangents aren’t just about making people laugh. They disarm and change the subject. They turn what could be an awkward moment into something else. He isn’t above deploying a survival mechanism.

I asked his oldest comedy friend, Greg Daniels, his partner at The Harvard Lampoon who went on to create the American version of “The Office,” if he believed that O’Brien no longer connected being funny with agony. He flashed a wry smile and said, “Then he drinks a whole bottle of hot sauce.”

O’Brien will say that he doesn’t live up to his own theories. Asked if he had ever wondered if his father wasn’t right after all about agonizing, he said, “I would not go back in time and have my dad say, ‘Hey man, chill.’”

THE STORIES WE TELL about ourselves matter even if they don’t fundamentally change us. O’Brien has been mulling his own story recently since, along with planning to tour and making a dramatic cameo in an A24 film by Mary Bronstein, he’s contemplating a book about his life. He noticed that in many memoirs, the authors always take credit for their successes or failures. “But what if I didn’t do anything?” he said. “What if they figure out there’s a little piece of zinc in people’s brains that makes us do what we do?”

This goes back to his belief that we do not matter. O’Brien, whose parents are in their 90s and who’s about to send his second of two children to college, has the perspective of age. He has seen peers think fame would make them happy, only to be disappointed.

He still agonizes. When he was 17, O’Brien wrote a fan letter to essayist-author E.B. White telling him he wanted to be an artist but worried about feedback. He was thrilled to receive a typed note in response.

“He said, ‘you’ve inspired me with your letter,’ which was crazy nice,” O’Brien recalled. “As for criticism, he wrote: ‘If that’s a problem, you don’t want to get into this business. I have gotten to the point when I only minded when they get their facts wrong.’”

O’Brien paused, marveling that he hadn’t listened. It reminded me of his brother’s mention of the documentary “Conan O’Brien Can’t Stop,” made after “The Tonight Show.” Luke O’Brien told me that title was accurate, even as a boy. Playing stickball, when everyone else would pretend to be famous players, Conan would imagine a guy with a complex back story like a “drug-addled shortstop with psychopathic tendencies.”

The night after his podcast taping, he was flipping channels until 2 a.m. He said that he is as terrified of putting himself out there as he was when he started performing. But now he knows that getting out of his own head, staying present, provides comfort and calm.

“I like those moments, like the eclipse recently, that remind me that I don’t count,” he said. “I’ve been through the late-night wars and I’ve trended and not trended and I know I have a certain skill set, and would like to be of use for as long as that’s viable.”

Then he paused and said solemnly, “And I would also like to acquire a vast amount of real estate in Montana,” starting a run. “I mean, a huge tract of land. Then I would like to frack on that land, because why not?”

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