Conan O.

Conan O’Brien houses the Academy Awards for the second time on Sunday, but it is something that may never have happened if he had stuck to what was proposed for David Letterman back in the early 1990s.

O’Brien revealed the strange part of “Jimmy Kimmel Live!” in Wednesday night, as the former talk show host extolled the joy of being a guest on a talk show.

“I really love being a guest, because when you’re the host, you have to worry about, ‘How do I get it?’ [a bit of crucial info] in conversation; I must come to this question; we are running out of time; I have to get out of the story,’” he explained.

“When you’re the guest, you don’t care,” O’Brien noted, pointing to Kimmel. “It’s your problem.”

Shortly afterward, Kimmel asked O’Brien what he thought about being a guest on Letterman’s show, and he said he thought it was “the scariest thing” he had ever done in his life.

O’Brien agreed, saying that Letterman was, to his and Kimmel’s generation, “our guy” and “we were like, ‘Oh my God, it’s Dave!'”

O’Brien then recalled the first time Letterman interviewed him in 1993, shortly after Letterman left NBC for News, leaving O’Brien to replace him as host of “Late Night.”

“My show was hanging by a thread. People were like, ‘Who is this guy? What kind of name is that? His hair looks stupid, he looks like a dessert,’ and people were really down on me, and I thought, I’m going to leave,” O’Brien said.

A lifeline came when Letterman asked to interview O’Brien on News.

“This is a great opportunity for me to save my show,” O’Brien said, adding that he discussed the appearance with the writers of his own show.

“What I love to do is present an idea that is intentionally bad, that I would never do, but that 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 on for a long time and never break.”

It provided a picture for viewers of Kimmel.

Jimmy Kimmel live on YouTube

One of O’Brien’s staff writers, Robert Smigel, previously wrote for Letterman and loved the idea, insisting that 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’m going off the air immediately! They’ll never invite me back; literally keep it up to the point where they kick me off Dave’s show,” he said, imagining the New York Post would have said he’d had a breakdown.

But although O’Brien insisted that such a move would have been bad for his short-term career prospects, he thought 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,” as Kimmel chimed in, “and Dave hates you!”

You can watch the full interview below, with Letterman’s portion starting around the 11-minute mark.

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