Both Oprah and David Letterman haven't been immune to awkward interviews during their time on top. Oprah faced Lindsay Lohan at her worst, while dealing with nonsense from her audience, like a fan discussing details about Brad Pitt's stomach tattoo when he was a guest on the show...The same held true for David Letterman and in fact, it might've been worse for Dave. Heck, he almost got his head kicked off by Crispin Glover back in the day.As for Oprah and Letterman together, things didn't always mix all too well. According to Letterman, the feud ignited over a restaurant bill, however, Oprah might see things differently, especially following their awkward interview in 1989. Let's take a look back at how it all took place.
David Letterman Thinks The Feud Ignited Over A Restaurant Bill
During their 1989 interview, David Letterman revealed that Oprah's hate for him started a long time ago. According to the legend of Late Night, he decided to have some fun with Oprah during a lunch. Letterman decided to leave Oprah with the bill. He retold the story.
“This predates the Academy Awards. She hated me long before then,” he said. “She was with Steadman (Graham). I was with my then-girlfriend Regina. We were both at a restaurant having lunch on vacation. I said to Regina, ‘Oh, this is hilarious. I’m gonna make Oprah buy us lunch."
He continues, “Oh, this woman right over there has been kind enough to take care of our check”. He and Regina then waved to Winfrey as they left the premises. “We got a free lunch and that’s where it started,” he recalled.
Straight out of the Dumb & Dumber playbook... However, Oprah said in the same interview that she didn't understand how that became a 'thing', and she wasn't bothered. In fact, Winfrey stated that she paid for the bill without even knowing Letterman's tab was on it.
Oprah Was Not Pleased With The Audience Reaction During Her 1989 Interview With David Letterman
This might be the very reason for the turmoil between Oprah and David Letterman. The interview took place in Chicago, and it was in front of a massive crowd that was quite loud throughout the episode.
The interview got off to a good start, but soon enough, it would get derailed completely and Oprah was visibly upset about it. She was coming off an episode that dealt with devil-worshipping... and of course, it got a reaction from the audience and Letterman himself.
When David brought up the subject, an audience member yelled, "rip her Dave," to which Winfrey was not happy with. Despite Letterman trying to laugh off the satanic-worshipping topic she discussed on her show, Winfrey withheld that it was an important topic and one that caused problems for people... though Dave mocked exactly how many people...
It was a moment that turned sour and looking back, Letterman believes Oprah grew angry due to the fact that he didn't defend her from the audience in that very moment.
“I think she resented the fact that I didn’t rise to the occasion and, you know, beat up on the guy. Which I probably should have, but I was completely out of control and didn’t know what I was doing”.
It wasn't the last time Letterman tried landing a joke at Oprah's expense...
David Letterman Bombed One Of His Oprah Jokes At The Oscars
Hosting the Oscars back in 1995, David Letterman added a bit more fuel to the fire in his feud with Oprah. However, looking back, David Letterman himself admitted that the joke fell completely flat and in fact, most of the audience didn't understand it.
Letterman said, "So it’s not like we’re introducing ‘Linda’ and ‘Diane’ to ‘Bob.’ We have Oprah — I don’t know that I know another Oprah, although there probably are hundreds of them now; same with Uma; and Keanu, I barely care about, but nonetheless, it’s still a different name. And I just thought, ‘Oh, this will be so fun and lighthearted.’”
According to Letterman, the joke was a last minute addition, and it lost its spark due to the fact that the cameras didn't go on the celebrities when he said their names. Letterman tried to salvage the joke, but it was clear, Oprah was the one to get the last laugh on this failed attempt.
