VIDEO: David Letterman Explains Why Oprah Hates Him

David Letterman explained his longtime bad blood with Oprah Winfrey in an entertaining story he told to guest Jon Stewart on Tuesday’s Late Show, proving wrong the cliché, “There’s no such thing as a free lunch.” 

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Letterman said that he was scared of Winfrey for a long time because “she hated me — that’s what it was.”

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Stewart, like everyone, thought the heat stemmed from Dave’s ill-fated “Uma-Oprah” joke at the 1995 Oscars.  Not so, said Dave.

“This predates the Academy Awards, this predates the Academy Awards,” Letterman said. “She hated me long before then.”

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Letterman said that the problems began when the two TV icons crossed paths at a pricey French restaurant where they dined with their significant others. Letterman said he told his then-girlfriend Regina, “this is hilarious … I’m gonna make Oprah buy us lunch.”

He then told the waiter Winfrey would be picking up their check, and pulled off the ruse when the waiter saw the show biz vets waving at one another, mistaking Winfrey’s cordiality as an acknowledgement she was going to pick up Letterman’s tab.

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The pair became friendly again in 2005, and this year filmed a Super Bowl commercial with another longtime Letterman foe, Jay Leno.

The Late Show
airs weeknights at 11:35/10:35c on CBS.


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