When he looked back on himself in those earliest broadcasts, O’Brien told me on Friday, he said he saw a performer attempting to fulfill competing desires. “We’re trying to be anarchists, but I’m trying to be a good boy and do a good job for the network,” he said. What he’s engaged in now, he said, “is this gradual progression toward me making the job fit me more — what do I like?”
Over breakfast in Los Angeles, O’Brien talked about the decision to restart “Conan,” the changes to the show and what might come next for him in his evolving TV career. These are edited excerpts from that conversation.
How does it feel to be so near to resuming the show, after being away for a few months?
My analogy is, in surgery, when they have to stop your heart so they can operate on you, there’s that weird moment when the doctor must be like, all right, time to start the heart up again! What if it doesn’t start? What if I walked out on the first test show and just started openly weeping? But we’ve done two test shows so far and it feels really good.
When did you first have the idea to take a break from the show and reconceive it?
Last year, I was coming up on 25 years as a late-night host. It made me realize, wait a minute, really? I remember when Johnny Carson retired, it was 30. At the time, that was such a big part of the story, that someone had had a television show for 30 years. It just struck me that the miles do add up. The repetition can get to you after a while. I was the new guy for so long, and then that card flips overnight — you go from the inexperienced, nervous punk to the old dean emeritus. I started to think, does it have to be that way? Let’s say I’ve got a couple years left in me. What if I tried to, in the most selfish way possible, alter this so that I have a maximum amount of fun? I decided to scare myself.
What led you to these other activities — the live tour, the podcast, the travel shows?
I had done a tour before, but this was no bells and whistles. I started out thinking, I need like 10 minutes up front. Then that became 15, then that became 20, then that become half an hour. By the end it was 40 minutes. It was really liberating.