Conan O'Brien's Near-Career-Ending Stunt on David Letterman's Show Revealed
Conan O'Brien is set to host the Academy Awards for the second time this Sunday, a prestigious gig that might never have materialized if he had followed through on a particularly audacious comedic idea pitched for an appearance on David Letterman's show in the early 1990s. O'Brien disclosed this bizarre anecdote during a recent episode of Jimmy Kimmel Live!, where he discussed the distinct pleasures and pressures of being a talk show guest versus a host.
The Talk Show Dynamic: Host vs. Guest
During the interview, O'Brien elaborated on the contrasting experiences. "I really love being a guest, because when you're the host, you need to worry about, 'How do I get crucial information 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. It's your problem," O'Brien noted, gesturing toward Kimmel to emphasize the point.
Kimmel then inquired about O'Brien's thoughts on being a guest on Letterman's show, describing it as "the scariest thing" he had ever done. O'Brien concurred, acknowledging that for his and Kimmel's generation, Letterman was "our guy," and the experience felt like "Oh my God, it's Dave!" This led O'Brien to recall a pivotal moment in 1993, shortly after Letterman departed NBC for CBS, leaving O'Brien to take over as host of Late Night.
A Desperate Time for O'Brien's Career
At that juncture, O'Brien's show was struggling to gain traction. "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 recounted. A potential lifeline emerged when Letterman invited him for an interview on CBS, which O'Brien saw as "a big chance for me to maybe save my show."
In preparation, O'Brien brainstormed with his writers, often pitching intentionally bad ideas for amusement. "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," he said. The specific idea he proposed was to sit beside Letterman and, when asked how things were going, suddenly "freeze and hold it for a really long time and never break." O'Brien even demonstrated this frozen pose for Kimmel's audience, highlighting the absurdity of the concept.
Writer's Enthusiasm vs. O'Brien's Caution
One of O'Brien's staff writers, Robert Smigel, who had previously written for Letterman, was particularly enamored with the idea and urged O'Brien to execute it. "You have to do it! You have to do it! Do it!" O'Brien recalled Smigel insisting. "It will blow people's minds, and overnight, people will say, 'This guy is a genius!'"
However, O'Brien harbored serious reservations about the potential consequences. "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 imagined, picturing headlines in the New York Post about a meltdown. While he acknowledged that such a stunt might have cemented his reputation among fellow comedians as someone who "showed the man," he foresaw a grim personal outcome. "And, meanwhile, I'm in an alley somewhere with no pants on," O'Brien quipped, with Kimmel adding, "and Dave hates you!"
Ultimately, O'Brien decided against the risky bit, a choice that likely preserved his career trajectory and paved the way for future opportunities like hosting the Oscars. This revelation offers a fascinating glimpse into the high-stakes world of late-night television and the delicate balance between comedic innovation and professional survival.
