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 this fall, has the perspective of age. He has seen peers think fame and success would make them happy, only to be disappointed.
He still agonizes, admitting to staying up one night worrying about the reception for his travel show. When he was 17, O’Brien wrote a fan letter to the essayist and 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 he made after leaving “The Tonight Show.” It was called “Conan O’Brien Can’t Stop,” and 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.” If he struck out, he would charge the mound pretending to hold a switchblade.
The night after his podcast taping, he couldn’t go to bed, flipping around channels until 2 a.m. He said that he remained as terrified of putting himself out there as he was when he started performing. The difference is he now 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,” he said, starting another run. “I mean, a huge tract of land. Then I would like to frack on that land, because why not?”
