All the details on Oprah and David Letterman’s feud

Oprah Winfrey and David Letterman are two of the most iconic broadcasters in television history. Winfrey rose to fame as the star of the hugely popular daytime show The Oprah Winfrey Show, which aired from 1986 to 2011.

A few years after the premiere of Winfrey’s show, CBS launched a late-night TV venture led by former standup comic David Letterman. Late Night with David Letterman premiered in 1982 and ran on NBC until 1993. According to the Los Angeles Times, Letterman’s move to CBS came after negotiations between the comedian and the network failed. According to the outlet, Letterman signed a $14 million deal to switch networks and was promised the coveted 11:30 a.m. timeslot.

Letterman and Winfrey have both retired from their daily talk programs after embarking on extremely lucrative careers. However, some may recall a messy feud between the couple that seemingly played out over two decades.

Oprah Winfrey felt disrespected on David Letterman’s show

Oprah Winfrey’s feud with David Letterman dates back to her first appearance on the late night show, which took place in the ’80s. Per Business Insider, Winfrey had an awkward interview with Letterman and declined to return in the future. A few years later, the comedian poked fun at the channel’s unique name while hosting the 67th Academy Awards. “I was dying to do something all day, and I think maybe we can take care of that,” Letterman said before introducing Winfrey and actress Uma Thurman to the packed audience. “Oprah? Uma. Uma? Oprah.” Letterman quipped before adding, “I’m feeling a lot better. Have you kids met Keanu?”

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And while many believed Letterman’s falling out with the Emmy-winning talk show host began with his joke at the Oscars, he’s since offered more insight into the true beginning of the feud. “This is older than the Oscars. She’s hated me for a long time,” 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 both went to a restaurant for lunch while on vacation. Letterman went on to reveal that he told the waiter that Winfrey would take care of the bill and he ended up getting a “free lunch.”

Oprah Winfrey and David Letterman have reconciled twice

Oprah Winfrey and David Letterman made two separate attempts to end their decades-long feud. In 2005, Winfrey attended the “Late Show with David Letterman” and tried to resolve the two’s dispute, and the host seemed just as excited about the meeting. “She’s huge. Put the past behind us, the water under the bridge, over the dam, wherever water goes — standing in your basement — she’s going to be here on this show and it’s going to be awesome,” the comic exclaimed (via Today).

During the interview, the two attempted to trace the origin of their alleged feud, but never fully addressed the issue. “I’ve never had a feud with you … I want you to know it’s really over, whatever you thought was happening,” Winfrey told Letterman.

It would be a few more years before the duo finally got to the root of their problem. In January 2013, two years after The Oprah Winfrey Show officially ended, Letterman joined the network for an episode of Oprah’s Next Chapter. During their conversation, the Chicago native explained why she refused to return to Letterman’s show after her first appearance. “It was a terrible experience for me. The guy in the audience started yelling, ‘Get her, Dave!’ They kind of baited the audience, and there were some drunk guys up front,” Oprah explained. Letterman has sincerely apologized for the moment, and it seems the two have officially moved forward now.

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