“I will be off the air immediately.”

Conan O’Brien remembers cut Letterman bit that could’ve killed his career

"I will be off the air immediately."

By Marina Watts

Marina Watts is a news writer for with seven years experience covering entertainment, pop culture and celebrity news. Her previous work appears in PEOPLE, Bustle and *Newsweek*.

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March 12, 2026 1:00 p.m. ET

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Conan O'Brien; David Letterman. Credit:

Jimmy Kimmel Live/YouTube; Kevin Winter/Getty

- Conan O'Brien reminisced on a bit that was cut from a David Letterman appearance that might've cost him his career.

- The comedian said he was planning to freeze in the middle of a response and hold it as long as he needed to.

- O'Brien returns to the stage at the Dolby Theatre to host the Academy Awards on Sunday, March 15.

Conan O'Brien's career could've ended before it even started.

During his Wednesday, March 11, interview on *Jimmy Kimmel Live*, the Academy Awards host reflected on appearing on *The Late Show with David Letterman*. Jimmy Kimmel asked O'Brien if the experience was "scary" for him. "Because for me that was the scariest thing I ever did," Kimmel added.

O'Brien said that for their generation, David Letterman was "our guy."

"This is a big chance for me to maybe save my show," O'Brien recalled thinking at the time. "We were sitting around with the writers and 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."

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So I said, "What if I come out and you're Dave and I sit down next to him and he says, 'Well, you know, this young man took over our show, and he's over there at NBC, and it's good to have you here, and now Conan tell me what's going on over there. How's the show going?'"

Conan O'Brien on 'Jimmy Kimmel Live' in 2026.

Jimmy Kimmel Live/YouTube

O'Brien proposed that while answering the question, he would freeze and hold it "for a really long time and never break."

Conan O'Brien and Jimmy Kimmel on 'Jimmy Kimmel Live' in 2026.

Jimmy Kimmel Live/YouTube

"While I do that, he's waiting for a bit and then the audience kind of is like, 'Huh?' And then everyone's weirded out." O'Brien said he was just making everyone laugh, but his head writer at the time, Robert Smigel, was game. "You have to do it. You have to do it. Do it. It'll blow people's minds," O'Brien said Smigel egged him on.

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"And I said, 'I will be off the air immediately. I will never be invited back.' I mean, literally hold it to the point where they carry me out of Dave's show," holding the pose, O'Brien continued.

O'Brien mused that perhaps the bit would've been a hit as time went on with older comics reminiscing on his genius. "Meanwhile, you know, I'm in an alley somewhere with no pants on," O'Brien quipped.

When Letterman retired in 2015, O'Brien penned an essay for **, praising his brilliance and how he reinvented the late-night format.

"Dave’s show was that rare phenomenon: a big, fat show business hit that seemingly despised show business," wrote O'Brien. "Dave didn’t belong, and he had no interest in belonging. He amused himself, skewered clueless celebrity guests, and did strange, ironic comedic bits that no one had seen on television before. Everything about that show was surreal and off-kilter."

Conan O'Brien and David Letterman on 'The Late Show with David Letterman' in 2012.

Jeffrey R. Staab/CBS via Getty

"Dave was a true revolution—and I believe his innovations are up there with the light bulb and the Twix bar," he continued. "Like all revolutions, it was such a seismic shift that it was disorienting and a bit messy at first, and it has taken us time to realize the sheer magnitude of the shift."

The Academy Awards air on Sunday, March 15, on ABC at 7 p.m. ET/ 4 p.m. PT. Watch O'Brien reminisce on his Letterman appearance in the video below.

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