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David Letterman at the 1995 Oscars

Hosting the Oscars has always been a rough gig. Every eye in Hollywood is on you that night and the next morning, or in the era of social media, while the show is still going on, everybody has an opinion about whether the host was great or terrible. Many hosts, like Bob Hope and Billy Crystal, have done well enough that they were asked back multiple times, others have had the job once, and then never again. David Letterman is one of those we haven't seen come back.

He hosted the awards show back in 1995 and while his appearance might not be one of the best in Oscar history, it's probably still one of the most memorable hosting gigs. If you were an Oscar watcher 25 years ago, and perhaps even if you weren't even alive (I've been told that's possible), you might be familiar with Letterman's infamous joke from his opening monologue, where he introduced Oprah Winfrey to Uma Thurman, and then did so several more times over the course of the bit.

The joke did not really work, but we're still talking about it a quarter century later, and talking to THR David Letterman reveals that part of the reason the joke likely didn't land was that it was a last minute idea, so even Letterman himself wasn't really ready for it. According to the former host...

And at the last minute, this tremendous, tremendous idea is offered to me from Rob Burnett, who was our head writer at the time [on Late Show], which was to go out and, ‘Hi, thanks, welcome to the show,’ and then go right to introducing Oprah to Uma, and then it was going to be paid off by having them say hello to Keanu. And by the way, this is a solid idea that I would do today if those three people were ever in the same room with me again — which seems unlikely, now that I think about it. But I said, ‘This is great, this will be perfect, this will supersede the jokes, this will loosen everybody up!’ Because unusual names — we have three!

The joke certainly has promise, Having some fun with Oprah and Uma's names has obvious comedy value. And yet, it simply didn't work out on the stage. Of course, part of the reason, if you remember the bit is that it doesn't play out exactly how David Letterman describes it here. Here's the monologue if you don't remember it, or have never seen it.

While David Letterman does introduce Oprah to Uma, and Uma to Oprah, he never does introduce either of them to Keanu. As it turns out, because the joke was put together at the last minute, Letterman didn't actually know where any of his targets were located in the theater, making focusing on them a little bit tough. You can see him in the video struggling a bit at the beginning. Letterman goes on...

One of the mistakes that I made was I didn’t tell anybody, ‘Maybe we need a shot of Oprah, maybe we need a shot of Uma, maybe we need a shot of Keanu.’ It never occurred to me. I just thought, ‘Once you say, ‘Oprah,’ well, the camera will swing around to Oprah.’ So I get out there, and I can’t find Oprah. Rob had said, ‘She’s stage left. You’ll find her.’ ‘OK.’ ‘And Uma is the equal position to the right.’ ‘Well, easy enough. Left and right.’ I get out there and I can’t find Oprah, and then I can’t find Uma, and I gave up looking for Keanu. So the whole thing was like a crazy man — ‘Well, maybe we’d better help Dad back to the home.’ So it was a great idea, but it needed some preparation. And then we were off and running!

Going back to a joke again and again, especially one that didn't quite land the first time, was a common move for David Letterman during his late night hosting days. Sometimes it worked, and the repetition itself became funny enough that the joke ultimately worked. Most didn't find that here and Letterman was pretty well roasted for his hosting of the Academy Awards in 1995. Even Letterman himself has said he thinks he did a terrible job.

Perhaps if, as Letterman says, the joke had received some preparation it would have worked better. It was basically the first bit out of the gate and it set the tone for the rest of the monologue and the rest of the night. Letterman's entire gig as host might have been viewed better if that silly joke had worked better.

The Oscars will avoid such questions for the second year in a row as the show will go without a set host.

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