Your tip
Your tip
RadarOnlineRadarOnline
or
Sign in with lockrMail

VIDEO: David Letterman Explains Why Oprah Hates Him

Sept. 29 2010, Published 8:55 a.m. ET

RadarOnline CommentsLink to FacebookShare to XShare to FlipboardShare to Email

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.” 

Watch the video on RadarOnline.com

Letterman said that he was scared of Winfrey for a long time because "she hated me -- that's what it was."

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

Article continues below advertisement

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

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.

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.

Radar Logo

Never Miss an

Exclusive

Daily updates from the heart of Hollywood, right to your inbox

By entering your email and clicking Sign Up, you’re agreeing to let us send you customized marketing messages about us and our advertising partners. You are also agreeing to our Terms of Service and Privacy Policy.

READ MORE ON Celebrity

Opt-out of personalized ads

© Copyright 2025 RADAR ONLINE™️. A DIVISION OF MYSTIFY ENTERTAINMENT NETWORK INC. RADAR ONLINE is a registered trademark. All rights reserved. Registration on or use of this site constitutes acceptance of our Terms of Service, Privacy Policy and Cookies Policy. People may receive compensation for some links to products and services. Offers may be subject to change without notice.