There is a misconception that’s been accepted as a popular culture fact for 22 years now. It’s a travesty that it has lasted this long, but it’s time we dispelled this nonsense once and forever. (And I hope you like how I’m prolonging the fake suspense of what it is I’m even talking about even though the subject is clearly in the title of this post.) Yes, I’m talking about David Letterman hosting the Oscars back in 1995. No, it wasn’t a “bomb.” No, it wasn’t “better than you remember.” It isn’t even “underrated.” In truth, David Letterman’s turn as Oscar host was legitimately great.
Letterman loved joking about his Oscars “bomb,” which fit perfectly into Letterman’s self-deprecating Midwestern humor. It was along the same lines as his yearly Passover joke (with the punchline being that he was passed over for The Tonight Show). But think about it, for Letterman it was the perfect scenario: Like his hero, Johnny Carson, he got to host the biggest awards show on the planet, yet he got to keep his outsider cred by being “bad” at it. And he played this up for years and years on his Late Show.
Now, do I think this was some elaborate plan from the start? No. What most likely happened was Letterman saw his mixed reviews and decided to lean into the bad ones for comedic effect, which he never stopped doing. So for 20 years, all we heard, from Letterman himself, was that he bombed. But when you go back and watch, it couldn’t be further from the truth. (And don’t be fooled, the Oscars very much wanted him back.)
Back in the ‘80s when Letterman was hosting Late Night on NBC, the network would give Letterman a prime-time anniversary special and these were, at the time, always pretty odd things. Taken away from the confines of late night television (or, to a lot of people in Generation X, the VHS recordings of Late Night that were watched in the morning before school), it’s just different. It’s still a wonderful thing for fans of Letterman, but you could almost hear the fuddy duddys complaining, Oh, who is THIS guy? This isn’t Johnny Carson. Wait, what is “Zippy and the Late Night Monkey Cam”?. Well, the same thing kind of happened when Letterman hosted the Oscars.