Letterman: Why Oprah Hated Me It happened long before 'The Incident,' he says By Evann Gastaldo, Newser Staff Posted Sep 29, 2010 8:38 AM CDT 4 comments Comments This photo, supplied by Harpo Productions, shows Oprah Winfrey welcoming first-time guest David Letterman to her 22nd season premiere at Madison Square Garden on Sept. 10, 2007. in New York. (AP Photo/Harpo Productions,George Burns) (Newser) – 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.