Why Did David Letterman & Oprah Winfrey Feud? A Walk Down This Bizarre & Hilarious Memory Lane

Well, it's the end of an era. As we all know, The Late Show With David Letterman officially closes up shop May 20. Understandably, fans of the late night host are probably getting all sorts of nostalgic, remembering highlights and lowlights from the show's 22-year run. Well, one thing some fans might be interested in is remembering the end of another type of era — the infamous feud between David Letterman and Oprah Winfrey.

At this point, the two are indeed friends, but it was not always smooth sailing between the two powerhouse hosts. Actually, that's an understatement. We're talking 20 years of frenemy status here, people. According to Business Insider, the feud started back in the '80s when Winfrey made an appearance on The Late Show and felt that it was an "uncomfortable" experience. This made her refuse to be a guest on the show again. In response, Letterman began cracking jokes about Winfrey and how much she hated him. This might have contributed to exaggerated rumors about her feelings toward him. But in any case, regardless of how much truth there was to the rumors, she did not speak to him for 16 years. So, obviously, this probably did not do much to quell the buzz about any hard feelings.

Since then, the two have made up — a couple of times — which has led to a very strange and somewhat confusing narrative that thankfully ended with them patching things up.

In 2005, the two attempted to bury the hatchet when Winfrey finally appeared on his show again. “Could you tell me please what has transpired?” Winfrey asked Letterman. “I have never for a moment had a feud with you.” Though the appearance was hyped up as a reconciliation, it seemed to be more of an exploration of how exactly the supposed fight started in the first place. And the conversation about the feud did not exactly end then.

In 2010, Letterman told Jon Stewart that Winfrey "hated" him due to a wild story about how he made her buy him and his then-girlfriend lunch when the two stars happened to be vacationing in the same spot.

Finally, in January 2013, Winfrey and Letterman officially put the feud behind them when Letterman made an appearance on an episode of Oprah's Next Chapter. Winfrey elaborated on why her appearances on The Late Show were uncomfortable for her. As she explained,

You had asked me before to do [your show] in Chicago... and it was a terrible experience for me. The guy in the audience started yelling, ‘Get her, Dave!’ You were sort of baiting the audience, and there were a bunch of drunk guys down the front. I was trying to like, you know, mitigate the whole thing, and it felt so uncomfortable to me. I didn't want to have that experience again.
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Once Letterman heard her side of the story, he apologized and said that he would be "embarrassed" to see the tape now.

So all in all, it has been difficult to say how much is exaggerated in this supposed feud and how much is spot-on. But in any case, it is nice to see that the two television titans have been able to put their own past behind them — despite confusing their respective audiences in the process.