Letterman: Why Oprah Hated Me

Oprah Winfrey’s longstanding, recently-ended feud with David Letterman was, everyone assumed, the result of his numerous “Oprah, Uma. Uma, Oprah” jokes at the 1995 Academy Awards. Not so, Letterman told Jon Stewart last night: “She hated me long before then.” Turns out the Late Show host pulled a dine and dash when he found himself eating lunch at the same restaurant as Winfrey on an island vacation, convincing the waiter the two knew each other and Winfrey had agreed to pay for his meal.

“I said to Regina, ‘This is hilarious, I’m gonna make Oprah buy us lunch,’” Letterman explained. After telling the waiter Winfrey would pay, he waved at her table and she waved back. “Now the waiter thinks, oh, well, sure. We got a free lunch. That’s where it started,” Letterman said. “That pissed her off. Not everybody likes horseplay.” Gawker has the video.
(More Jon Stewart stories.)