The surreal feud between Oprah Winfrey and David Letterman
In terms of contemporary American talk show hosts, Oprah Winfrey and David Letterman are two of the finest, despite what fans of Ellen DeGeneres might say. The pair have interviewed numerous icons over the years, ranging from royalty to pop stars. For a long time, their shows have been a place in which the most influential figures in popular culture feel comfortable enough to throw off the cloak of privacy and be more candid about their lives than ever before.
However, although they are both masters at conducting interviews, for a long time, the pair were locked in a strange rivalry that had everybody else perplexed. It has been reported that the two had a feud that lasted more than two decades, with Oprah refusing to speak to Letterman whenever they bumped into each other.
Per an account in The Huffington Post, it all started when Oprah appeared on The Late Show with David Letterman in 1989, and for her, it was an “uncomfortable” experience, to say the least. The crowd were angry, as the night before, she’d hosted a TV show about devil-worshipping, which was a complete disaster due to the outlandish claims of some of her guests that she seemed to entertain, including a deranged woman called Rachel. When on Letterman, the crowd were so heated that one guest even called on the host to “Rip her, Dave”.
Later, Letterman explained why he felt Oprah got so angry at him: “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”.
Admittedly, the late-night talk show host did not help matters, as afterwards, he would make quips about Winfrey’s feelings towards him and exaggerate the situation. Letterman even claimed he was ill because he ate clams at her restaurant, The Eccentric.
Letterman later made things worse in 1995 by tearing into Oprah during his duties as the Academy Awards host. “I’ve been dying to do something all day, and I think maybe we can take care of this,” he said before introducing Winfrey and one of the biggest stars of the day, Pulp Fiction star Uma Thurman. “Oprah? Uma. Uma? Oprah,” Letterman quipped about their names before adding: “I feel much better. Have you kids met Keanu?”
Despite Letterman being rude, Oprah’s real hatred started years earlier, in a different moment from her appearance on his show back in 1989. Speaking with Jon Stewart in 2010, Letterman explained that Oprah hated him after he left her with his bill at a restaurant they were both eating in.
“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.'”
When the time came to pay the bill, Letterman told the waiter, “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.
Although the feud is one of the most ridiculous in history, the pair did makeup when Winfrey finally made another appearance on The Late Show in 2005. “Could you tell me please what has transpired?” Oprah asked Letterman. “I have never for a moment had a feud with you….I want you to know, it’s really over, whatever you thought was happening”.
