O'Brien refused to divulge what he has planned for his last performance, though he did shoot down one possibility. “There is a rumor that people are going to see my naked body for the first time,” he deadpanned. “But that's not going to happen.”
His last sign-off will trigger a shuffling in late-night television that the comedy world has been chattering about for five years, ever since NBC announced that O'Brien would succeed Jay Leno on “The Tonight Show.” After much speculation that the network would ultimately back out of the deal, that handoff is now just months away: Leno will host his final program on May 29 and O'Brien will take over the show June 1.
But before then, he has to wrap up his time on “Late Night,” which Jimmy Fallon begins hosting March 2. The process has triggered “a mixture of excitement, dread and the sense that you're having a nervous breakdown, a swirling cone of three flavors,” O'Brien said in a phone interview.
“There's an enormity to it that's very hard to process,” he added. “I mean, this has been such a big part of my life.”
O'Brien has spent much of the last week reflecting on his early days at “Late Night,” when the then-unknown comic and television comedy writer took over for David Letterman after the latter defected to CBS.
In reviewing old episodes, he said there have been surprisingly few cringe-worthy moments, other than occasionally wincing at his appearance. Back when he met his now-wife, “she was cooking me pasta all the time, so there was this period of time around 2000 that I sort of started to resemble Daniel Patrick Moynihan,” he quipped.
Mostly, said O'Brien, a former writer and producer for “The Simpsons,” “I look back on that young guy and I think, You have no idea what you're in for.' I have an affection for that guy because he's out there, and he's giving it everything he has, and so I feel like he's naive but well-intentioned.”
After a rocky start, O'Brien has held onto the top spot at 12:35 a.m. for 14 seasons. But recently, CBS's Craig Ferguson has made gains, raising questions about how O'Brien will fare with the “Tonight Show” audience.
Complicating matters is the fact that Leno will still be around, hosting a nightly 10 p.m. comedy show that debuts in the fall. O'Brien said he's not worried that it will be difficult to get out from under Leno's shadow.
“I was relieved that Jay and NBC reached an amicable arrangement,” he said. “I like Jay, and we're friends, and I'm happy that Jay is happy. And on the business side of things, Jay has been a really good lead-in for me, and I think that's going to continue to be the case.”
“You know, I have this religious faith that there's something very special about NBC at 11:30,” he added. “It's been the case for 60-some odd years, and I am a believer that there is meaning to that show and to that time period.”
As he prepares to make the move from New York to Los Angeles, O'Brien has been pondering how to calibrate his comedy for the storied “Tonight Show,” a process he said has been assisted by watching old “Late Night” episodes.
“It puts you face to face with the biggest reality of specifically this kind of entertainment, which is that you're always changing,” O'Brien said. “I hate to sound like a qigong class at a spa, but you're always in the process of becoming whatever performer you're going to be.
“So it's been really healthy for me to look at all this stuff and realize this has been a kooky journey and the Tonight Show' is just a continuation. Ripping this plant out of 51st Street in Midtown Manhattan and dropping it down in the nutrient-rich soil of Los Angeles, it's going to change in some ways that I can't even probably tell you right now,” he said.
“I basically want the Tonight Show' to be a very powerful incentive to think of new things,” he said, adding that he thinks of the program of as “a fish-out-of-water comedy.”
“I think that I'm going to be wearing a lot of floppy hats,” said the pale redhead. “We're going to have a lot of segments where a dermatologist comes out and checks me. It will be a regular feature on the monologue: Conan Gets a Cancer Screening.' “
While “a lot of New Yorkers act like I'm being shipped off to some remote Marine base in Guam,” the Boston-bred O'Brien said he's looking forward to the move to Los Angeles. It was there that he got his start as a writer for HBO's “Not Necessarily the News.”
“I hate leaving New York City -- it's been a great home to me,” he said. “But things really did start for me in Los Angeles, and it's been a lucky place for me. So I'm looking forward to it. And I also think frankly if I was going to continue with television, there are a lot of miles on my comedy odometer. We need drastic change to try and reconceive this show in good ways, and I think putting us in Los Angeles, on the other side of the country, a place I'm genetically not engineered to exist in, could be just the ticket for us.”