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

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.