Conan O’Brien‘s Oscars debut earlier this week was a dream come true for fans. But for another former late-night host, O’Brien hosting the Oscars was his worst nightmare come true.
No, we’re not talking about Jay Leno. An O’Brien-hosted Academy Awards was the bad dream conjured up by David Letterman thirty years ago this month.
Letterman depicted the scenario in an episode of Late Show with David Letterman in March of 1995, less than a week before he himself hosted the Oscars for the first and only time. Dreading his upcoming gig, Letterman told viewers that he’d been suffering a recurring nightmare. “It’s always the same, and yet just different enough to terrify the holy hell out of me,” he said before staging the dream.
“And now, please welcome the host of the 67th Annual Academy Awards,” an announcer bellows in the nightmare as a tuxedoed Letterman excitedly approaches the Oscars podium.
“…Conan O’Brien,” the voice continues. With that, O’Brien steps out in front of Letterman at the podium. O’Brien had taken over Late Night from Letterman just a year-and-a-half prior when the bit aired, and the two enjoyed a cordial relationship. O’Brien had guested on Late Show twice before this cameo, and Letterman had paid a visit to Late Night with Conan O’Brien.
While O’Brien’s Academy Awards debut was widely well-received this year, Letterman’s 1995 performance wasn’t as successful. His Oscars-related nightmares may have been prescient, as the host wound up delivering a performance that both he and critics remember less fondly.
Letterman’s nightmare-turned-premonition can be viewed above, thanks to Letterman archivist Don Giller.
