The Night David Letterman Bombed the Oscars

Twenty years ago, the legendary late-night host tried his shtick on Hollywood's biggest night. It didn't go well.

Oprah Winfrey evidently forgave David Letterman for making fun of her name at the 1995 Academy Awards. The two are shown here in 2012. (Chris Bergin/Reuters)

As Neil Patrick Harris prepares to host the 87th Academy Awards ceremony on Sunday, he won't need to look far in the past to find examples of what not to do. There was Seth MacFarlane, whose performance in 2013 was deemed "misogynistic" and "crudely sexist" by The New Yorker's Amy Davidson. But at least MacFarlane showed signs of life—which was more that can be said about James Franco. Hosting with Anne Hathaway in 2011, the somnambulant Franco showed about as much energy as a throw pillow. Even the 2009 outing by the talented Hugh Jackman, whose skill set most closely resembles Harris's among Oscar hosts, was widely seen as a failure.

But the gold standard of Oscar bombing remains David Letterman, whose notorious turn as host is now 20 years old. In 1995, the late-night host was at the peak of his career. His Late Show, which debuted on CBS two years before, was wildly popular, consistently beating NBC's Tonight Show, hosted by Letterman's bitter rival Jay Leno, in the ratings. But almost from the minute the Oscars began, it became clear that it wasn't going to be Dave's night.

Noting an aural similarity between the names of two prominent female celebrities, Dave launched into a trance-like routine. "Oprah. Uma. Oprah. Uma. Oprah. Uma. Have you kids met Keanu?" Few laughed. And then things got worse. Jokes about Tim Robbins and Arnold Schwarzenegger landed with a thud, and attempts to graft popular bits from the Late Show—like the "Top 10" list—didn't work.

The critical reception was savage. The New York Times accused Letterman of leaving the show's "pacing in shambles," and added that "glamorous people waiting for awards announcements aren't terribly interested in New York City cabdrivers or stupid-pet tricks."

So what can Neil Patrick Harris learn from the Letterman's experience? The first lesson is that it's fine to snark at Hollywood stars—provided you are one yourself. Dave, for all of his fabulous success in comedy, never strayed from the medium, and his outsider shtick didn't work for the ceremony. As Conor McKeon wrote of Letterman in 2011:

Having a show based in New York City means Hollywood comes to him. It’s telling that the first laughs of the night came when Letterman said, “I won’t lie to ya, I’m very, very excited.” Letterman didn’t care whether he was beloved, and everyone knew it.

Fortunately for Harris, who the long-term consequences for bombing at the Oscars are low. Hathaway, Jackman, and MacFarlane have had little trouble finding work in the years since their failed stabs at hosting. As for Letterman, he retires this year as arguably the most successful, popular late-night host ever. (And, he confided to The View in 2010, he was even approached to host the Oscars again.) No matter what happens on Sunday, Harris won't have to worry too much.

But he might want to go easy on the Uma/Oprah jokes.