Despite What You’ve Heard, David Letterman’s Oscars Were Actually Really Great

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.

By 1995, Letterman had been hosting Late Show at CBS for about a year and a half and had long said goodbye to Zippy and the Late Night Monkey Cam. But Letterman was still doing his Top 10 list and he was doing Stupid Pet Tricks. And this is how you get that year’s Best Actor nominee Tom Hanks on stage with a dog that chases its tail around when she hears applause. (I remember watching this live and being in heaven. I couldn’t believe this was happening at the Oscars. Of course, some critics at the time weren’t amused a dog was doing a trick on the immortal night we all honored Forrest Gump. They were wrong.) After it ended, Tom Hanks leaves the stage and Letterman asks him, “That was just as good as winning something, wasn’t it” (Yes, it was.)

Of course Dave did shtick from his late night show! What else was he going to do And the thing is, now that we’ve been missing Letterman’s voice in our current political climate (even though he still pops up here and there), Letterman’s Oscars takes on a new meaning. Sure, in 1995 you could have complained that if you wanted to watch Letterman’s show, you would have just watched the Late Show (that was a bad opinion, but okay). But now, in a world where we can’t just do that anymore, it’s even more amazing that Letterman pulled off that particular Oscars.

“But what about the Uma-Oprah joke” Rewatching it now (which you should), it’s true that when Letterman introduces Oprah Winfrey to Uma Thurman, it doesn’t get a particularly large laugh. As his monologue goes on, he tries it with other names and it never really clicks. But in classic Letterman fashion, he keeps referencing his failed joke as a form of self-deprecation. This is what Letterman always does: He keeps pounding his failed joke over your head until it becomes funny. And by the end, I was laughing.

Letterman’s monologue also has a great pre-taped bit where asks New York City cab drivers about the Oscars – and it does come off a little bit like “Yeah, normal people don’t really care about all you phonies out in Los Angeles,” but who cares Unless you are a phony and also happen to live in L.A., it’s funny. It ends with Letterman’s Jack Nicholson impression: Dave hitting a cab with a golf club, which was a play on a recent (at the time) altercation Nicholson had with a golf club and a car.

And the best thing: Letterman’s non-stop badgering of the Academy for not nominating Hoop Dreams – something that, 22 years later, is still preposterous. (In Letterman’s Top 10 list, which supposedly people didn’t like, the line about Hoop Dreams got a tremendous applause.)

And then there are the Cabin Boy line readings. And again, this was Letterman being self-deprecating. The year before, Letterman had appeared in Chris Elliott’s movie, Cabin Boy (a film I actually saw in theaters), and appeared as a character named Old Salt (I knew that without looking it up) who asks Elliot’s Cabin Boy character if he wants to buy a monkey.

Letterman got a who’s who of star power to “audition” for the role of Old Salt. Most notably, Paul Newman appears. Paul Newman! (Newman enjoyed playing a foil to Letterman. During Letterman’s first show at CBS, Newman appears in the audience and asks, “Where the hell are the singing cats” before walking out.) But there’s Paul Newman, in on the joke, even though 1995 wasn’t quite ready for any of this yet.

Maybe that’s what people weren’t used to at the time: Letterman was the first comic who used his brand of irreverent humor to host the Oscars. In the ten years prior to Letterman, here are the people who hosted or co-hosted:

Whoopi Goldberg

Billy Crystal (four times)

Chevy Chase (twice)

Goldie Hawn

Paul Hogan (!)

Robin Williams

Jane Fonda

Alan Alda

Jack Lemmon

I suppose Chase comes the closest – his humor can certainly be irreverent – but it’s a different brand. It’s more pratfalls and quick one-liners. (I’m going from memory, but I do remember Chase falling through some sort of trap door while hosting.) Regardless, that’s quite an elegant crowd. In 1995, Letterman stood no chance against that group. In 2017, it would be a different story. I promise if Letterman hosted the exact same show today, we’d all think it was great. So don’t let anyone fool you (especially Letterman himself): David Letterman hosted a fantastic Oscars and the tragedy of it all is that we only got one from him. (I realize it’s still technically possible, but that will never happen. Also, yes, I would certainly buy a monkey from Paul Newman.)

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