Conan O’Brien hosts the Academy Awards for his second time on Sunday, but it’s something that might never have happened if he had stuck to a proposed bit for David Letterman back in the early 1990s.
O’Brien revealed the bizarre bit on “Jimmy Kimmel Live!” on Wednesday night while the former talk show host extolled the joys of being a talk show guest.
“I really love being a guest, because when you’re the host, you need to worry about, ‘How do I get [a bit of crucial info] into the conversation; I gotta get to this question; we’re running tight on time; I gotta get out of the story,’” he explained.
“When you’re the guest, you don’t care,” O’Brien noted and pointed to Kimmel. “It’s your problem.”
A short time later, Kimmel asked O’Brien his thoughts about being a guest on Letterman’s show, saying he found it “the scariest thing” he’s ever done.
O’Brien agreed, saying Letterman was, for his and Kimmel’s generation, “our guy,” and “we were, like, ‘Oh my God, it’s Dave!’”
O’Brien then remembered the first time he was scheduled to be interviewed by Letterman in 1993, a short time after Letterman left NBC for CBS, leaving O’Brien to replace him as host of “Late Night.”
“My show was hanging on by a thread. People said, ‘Who is this guy? What kind of name is that? His hair looks stupid ― it looks like a dessert,’ and people were really down on me, and I thought, I’m gonna go away,” O’Brien said.
A lifeline came in when Letterman asked to interview O’Brien on CBS.
“This is a big chance for me to maybe save my show,” O’Brien said, adding that he discussed the appearance with writers on his own show.
“What I love to do is pitch an idea that is intentionally bad, that I would never do, but it just makes the writers laugh,” O’Brien said.
O’Brien’s intentionally bad idea was to sit next to Letterman, and when the host asked him how things were going, he would suddenly “freeze and hold it for a really long time and never break.”
He provided a visual for Kimmel’s viewers.
Jimmy Kimmel Live via YouTube
One of O’Brien’s staff writers, Robert Smigel, previously wrote for Letterman and loved the idea, insisting he do it on the show.
“You have to do it! You have to do it! Do it!” O’Brien remembers Smigel telling him. “It will blow people’s minds, and overnight, people will say, ‘This guy is a genius!’”
O’Brien had a different thought.
“I will be off the air immediately! I will never be invited back ― literally hold it to the point where they carry me out of Dave’s show,” he said, while imagining that the celebrity.land would have said he had a meltdown.
But while O’Brien insisted a stunt like that would have been bad for the short-term prospects of his career, he figured that many years later, his fellow comedians would remember that time O’Brien “showed the man.”
He added, “And, meanwhile, I’m in an alley somewhere with no pants on,” while Kimmel interjected, “and Dave hates you!”
You can see the complete interview below, with the Letterman bit starting around the 11-minute mark.
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