Conan O’Brien Still Think It Was A Mistake That He Got David Letterman’s Old Job
Conan O’Brien says there must have been some mix-up that led to him becoming a late-night TV legend, and he’s right — NBC giving Jay Leno the The Tonight Show was probably a poor choice.
It’s been more than three decades since NBC replaced the outgoing and mildly spurned Late Night host David Letterman with a lesser-known comedy writer fresh from the Simpsons staff, and even with the benefit of seeing where Conan’s career took the entire medium of late-night comedy in the years that followed, the red-haired, 6-foot-4 Harvard grad still seems like an odd pick for one of the most important jobs in television. When he took the Late Night job in 1993, O’Brien wasn’t a seasoned stand-up star like the rest of the late-night community at the time, and his name carried no weight outside of the circles that watched “Marge vs. The Monorail” all the way through its end credits.
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Today, Conan is, of course, a comedy giant at the head of a veritable media empire who is currently preparing to host the upcoming Academy Awards. And, yet, he still feels like an imposter who isn’t fit to carry Letterman’s leather jacket.
On Monday’s episode of Conan O'Brien Needs a Friend, the now-legendary former late-night host admitted to his guest Adam Scott that his reverence for his predecessor Letterman started when he was still a Harvard student, and that respect lives on today as a deep-seated inferiority complex. “The first time that I saw Letterman’s show …. I was in college and I went to New York and saw a live taping of Late Night with David Letterman having no idea that I would take over that show in that studio and that some of those crew members would be my crew members,” Conan recalled.
“I remember being led in by NBC pages and sitting down and thinking, ‘What’s going on? This is really small!'” Conan said of his first impression of his future workplace. “Because, on television, the perspective is widened, and things look big. And (I’m) realizing, ‘Wait a minute, what the fuck? Where Dave is standing and doing his monologue, he can reach over and touch Paul Schaffer. He can touch him.’”
Now, Conan understands the construction of the NBC soundstage that would become his home for 18 seasons, explaining, “Studio 6A is, notoriously, it’s a small — it was built for radio. That’s the magic of it is that it’s small. So comedy rockets around the room and bounces off the walls.”
But back during his first introduction to the biggest small stage of his career, Conan was just a star-struck student tagging along with a friend who knew a writer on Letterman’s Late Night, a fellow Harvard alumn Steve O’Donnell, who helped Conan get his first brush with greatness. Conan remembered, “Steve brought us up to the offices and we’re sitting in Steve O'Donnell’s tiny office. … and Merrill Markoe walks by, and a guy in a leather jacket walks by with her carrying a box, and it’s Dave Letterman.”
“He kind of just nods at us and keeps moving,” Conan said of his first interaction with his future forerunner, joking of the awe Letterman inspired in him, “If I was a kid, I would say it was like the President of the United States walked by, but that no longer works.”
“I’ll never forget it,” Conan said of his first Letterman sighting. “I remember the jacket he was wearing. I remember thinking, ‘Wow, he gets to have this show.’ … And then the idea that, 10 years later, I’m hosting that show, to this day makes no sense to me, and I think it was a mistake.”
Conan reiterated of his big break on Late Night, “I really do, in my heart, think it was a fucking blunder.”
Well, it certainly wasn’t as bad a blunder as making Leno Conan’s lead-in — looking at you again, NBC.
