Conan O'Brien's career is still evolving after Late Night. (2024)

NEW YORK -- 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 when he proposed that all statues and monuments should be made with durable soap that dissolves in seven years. A month later, 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."

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.

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. His post show work may turn out to be more impressive.

It helps that his brand of joyfully goofy absurdity ages well. 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 has 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 increasing 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.

The most revealing aspect of O'Brien's return to his old show might have been that it was overshadowed by "Hot Ones." O'Brien made every other episode look bland, 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. "Conan O'Brien" trended on social media for days.

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 Sirius for a staggering US$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 has not shifted course so much and has 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.

His unlikely talk-show career, initiated when Lorne Michaels plucked him from obscurity to take over for Letterman at "Late Night," began with a cold open in which he walked through New York while everyone, from girls playing hopscotch to a talking horse, reminds him that he is under a lot of pressure and that he "better be as good as Letterman." It is 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 humour as a survival mechanism. But after considerable therapy and reflection, he has come to believe that so much stress did not help him be funnier. 'Looking back now, I think some of my best ideas came from just goofing around," he said.

His freewheeling podcast 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.

These new projects do not 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 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 theatre, 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."

This article originally appeared in The New York Times.