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Oprah Winfrey’s feud with David Letterman dates back to her first appearance on the late-night show, which occurred in the ’80s. Per Business Insider, Winfrey had an uncomfortable interview with Letterman and refused to return in the future. A few years later, the comedian poked fun at the broadcaster’s unique name while hosting the 67th Academy Awards. “I’ve been dying to do something all day and I think maybe we can take care of this,” Letterman said, before introducing Winfrey and actor Uma Thurman to the crowded audience. “Oprah? Uma. Uma? Oprah.” Letterman quipped before adding, “I feel much better. Have you kids met Keanu?”
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And while many believed that Letterman’s quarrel with the Emmy-winning talk show host began with his joke at the Oscars, he has since provided more insight into how the feud really started. “This predates the Academy Awards. She hated me long before then,” Letterman told Jon Stewart during an episode of “Late Show with David Letterman,” (via HuffPost). “She was with Steadman, 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.'” Letterman went on to reveal that he told the waiter that Winfrey would take care of the check, and he ended up with a “free lunch.”