Conan O’Brien Doesn’t Matter

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. One month later, in his office in Los Angeles, down the hall from his podcast studio, he went further, declaring 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, leaning forward and shifting to a less jokey tone. “We don’t matter.”

Since leaving late-night television in 2021, Conan O’Brien, 61, has become more reflective about life (and death), given to philosophical flights of fancy that he compulsively alternates with comic tangents. O’Brien famously 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, Conan O’Brien has built one of the most consequential careers in comedy. And while 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 repeatedly beaten him out for Emmys during 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 and open to 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.”