David Letterman Talks Bombing As Oscars Host 25 Years Later: ‘The Single Biggest Professional Embarrassment Of My Life’

It’s been 25 years since David Letterman’s disastrous gig as Oscars host, and now he’s finally looking back at the mess that was.

The former “Late Show” host sat down for an interview about the 1995 Academy Awards with The Hollywood Reporter.

“I just want to thank you and the entire show business community for helping me to celebrate 25 years after the single biggest professional embarrassment of my life,” Letterman joked.

The 72-year-old had already hosted the Emmys in 1986 before taking the Oscars M.C. job.

“I wouldn’t say I enjoyed it. 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,” he recalled. “It certainly wasn’t the explosion of excrement that the Academy Awards was, but it was not great.”

Letterman admitted that he was hesitant to sign on as Oscars host.

“I had seen Billy Crystal, who, at the time, was the new type of host — and beloved. And I knew, Well, I can’t do that,” he said. “And I knew that I can’t just [tamely joke], ‘Oh, congratulations, Linda! Thank you very much! Bob, good to see you again! Nice shoes, Bob, where did you get those? Costco?’ And I started to get scared realizing, Maybe I don’t belong here.”

One of the most memorable moments of the night was Letterman’s gag about Oprah Winfrey and Uma Thurman’s names, which did not go over well with the audience.

“Well, when I was done with the monologue, we had a videotape to play, so they put you in some kind of [backstage] structure that you might see in the showroom at Cabela’s, and you sit in there. I was talking to Rob and Robert Morton [a ‘Late Show’ producer], and I said, ‘Well, what do you think?’ And Morty said, ‘Yeah. It was okay.’ So now I’m thinking, Oh, Jesus. And I said, ‘Was it just—?’ And he said, ‘No, no, it was fine.’ And I thought, Fine?”

“And finally I browbeat the poor man into saying, ‘You know, it was great!’ And I thought for the first time in my life, I’ve gotten someone to lie to me about my own performance,” Letterman continued. “I felt horrible about that. We went from ‘fine’ to ‘great’ in about a 15-minute conversation, and that was my first realization, other than the heavy perspiration.”

Despite flopping, Letterman revealed he was asked to return as Academy Awards host in following years.

“Yes, I was, I think two different times. And I don’t know how that happened — maybe a new guy came in who hadn’t seen the original?” he said. “And I considered it and then I thought, What, are you crazy? No! Because I knew the same thing would happen again. But I will say: Billy Crystal followed the next year and was kind enough to include a bit of comedy with me that allowed me to kind of knock the ugliness off the event — it was a reference to Oprah-Uma, and I think it went pretty well. It wasn’t enough to kick the taint off the night, but it was very generous of Billy to do that.”