David Letterman reflects on disastrous Oscars hosting stint: ‘The gold standard of Oscar bombing’

TV host became the subject of ridicule after his many jokes about Hollywood A-listers fell flat

David Letterman has reflected on his disastrous 1995 stint as Oscars host for the first time, calling it the “single biggest professional embarrassment” of his life.

The TV host became the subject of ridicule after his many jokes about Hollywood A-listers fell flat. He was named by Time magazine in 2011 as the worst awards show host ever, while The Atlantic branded it “the gold standard of Oscar bombing”. A report in the New York Times the day after the ceremony was headlined: “The Winner Isn’t David Letterman.”

Letterman was approached to host the Oscars nine years after emceeing the Emmys with Shelley Long, in 1986.

“I wouldn’t say I enjoyed it,” he told The Hollywood Reporter. “I really thought, ‘Oh, well, this will be good, because I can come out and make fun of people.’ And it turned out I was wrong. It certainly wasn’t the explosion of excrement that the Academy Awards was, but it was not great.”

Arguably the most maligned part of Letterman’s Oscars performance was a gag where he tried to point out some of the more unusual names in attendance: “Oprah? Uma. Uma? Oprah?... Have you kids met Keanu?”

Both Oprah Winfrey and Keanu Reeves were presenting awards that year, while Uma Thurman was nominated for her performance in Quentin Tarantino’s Pulp Fiction.

“In my mind, we have these three people, highly respected and of great status in the popular culture, in the same room, so it’s not like we’re introducing ‘Linda’ and ‘Diane’ to ‘Bob’,” Letterman explained. “We have Oprah – I don’t know that I know another Oprah, although there are probably hundreds of them now; same with Uma; Keanu, I barely care about, but nonetheless, it’s still a different name. And I thought, ‘Oh, this will be so fun and lighthearted.’”

Letterman recalled a moment later on in the ceremony when actor and comedian Steve Martin presented an award, and commented: “I really enjoyed Dave’s opening monologue... but then again, I also like cleaning up after my dog.’

“And I just thought, ‘Oh my God, Steve Martin hates me.”

Letterman reveals that he was asked to host the Oscars twice more after that fateful night: “I considered it and then I thought, ‘What, are you crazy?’”

This year’s Academy Awards will once again take place without a host, following the success of last year.

See our ranking of the five best and five worst Oscars hosts of all time here.