Anyone who has watched David Letterman over the years knows that Oprah Winfrey hates him — or so Letterman thinks, or would like the audience to think. He’s used her alleged hatred of him and their alleged feuding as a comedic foil for years, and used it to great effect when Winfrey appeared on “The Late Show” to promote the debut of her soon-to-be-blockbuster Broadway production of “The Color Purple.”
During Tuesday night’s “Late Show with David Letterman,” the late night host finally came clean about why he believes Oprah Winfrey hates him. With fellow funnyman Jon Stewart as his guest, Letterman explained what started the his feud with the Queen of Daytime Television.
Jon Stewart of “The Daily Show” made the journey all the way to Ed Sullivan Theater (several long blocks from Comedy Central’s studios) to promote his new book, Earth: A Visitor’s Guide to the Human Race, on Tuesday’s show. But the talk turned to other matters and the book was barely mentioned, as Stewart apparently triggered David Letterman’s need to confess. After discussing their children and the “Rally To Restore Sanity,” Letterman and Stewart finally got around to the world’s favorite topic: Oprah Winfrey.
Stewart appeared on “The Oprah Winfrey Show” during premiere week — also to promote his book. Everyone in the audience received a copy, which, as Stewart pointed out, wasn’t quite the same as getting an all-expenses paid trip to Australia (which she gave away on her season premiere show). But, Letterman noted, they’d need something to read on that long trip…
They talked about what a nice and generous woman Oprah Winfrey was and Letterman, who called her “transcendent,” admitted he was intimidated by her. Her power made him feel as if she could “crush me like a bug,” he said at one point. Stewart asked why he felt that way. “She hated me,” Letterman said.
Stewart protested. Letterman insisted. He said, “This predates the Academy Awards. She hated me long before then,” Letterman told Stewart, pointing to where legend has it that the Letterman-Oprah feud began — with comparative comments about Uma Thurman and Oprah Winfrey when he hosted the Oscars. When prompted by Jon Stewart to tell why Oprah hated him, David Letterman did.
It seems that early in their careers, both Oprah and Letterman were vacationing on the same island. One day while Letterman and his girlfriend at the time, Regina Lasko, were at a restaurant, Winfrey walked in with longtime beau Stedman Graham. Letterman said, as a joke, he told his girlfriend that he was going to get Oprah to pay for their meal.
So Letterman told the waiter that the lady at the other table had graciously offered to pick up his check. As a parting touch, as he and his girlfriend left, Letterman caught Oprah’s eye and waved to her (she waved back), further setting the hook for the unknowing waiter.
“We got a free lunch; that’s where it started,” he said.
“You dined and dashed on Oprah?” Jon Stewart laughed, mock incredulously.
For the record, during her appearance on his show in 2005 to promote and launch “The Color Purple,” Winfrey told him that she had no idea why he thought they were feuding. “Could you tell me please what has transpired?” she asked Letterman. “I have never for a moment had a feud with you….I want you to know, it’s really over, whatever you thought was happening.”
So now the world knows the story behind the famous feud. David Letterman has feared the power and wrath of Winfrey, who became one of the most powerful women in television and who is considered one of the most important and powerful figures in the world (not to mention one of the wealthiest), because of his guilt for stiffing her for a meal as a joke several decades ago.
Or so Letterman would have his audience believe — and Stewart, who was there to sell his book, just as he had been on “The Oprah Winfrey Show.” No mention was made that in the book, Earth: A Visitor’s Guide To the Human Race, Stewart (and the “Daily Show” writers, who contributed to the tome) noted that an alien race faced with an empty Earth would no doubt find all the images, videos, and writings about Oprah testimony that she was looked upon as a god.
Perhaps it was just as well. David Letterman already seems to think that she’ll one day use her considerable power to bring him down. And perhaps that is exactly what Oprah wants him to think, getting the last laugh and teaching him not to be dishonest. Besides, isn’t that what gods do: teach the rest of us lessons?
The segment of the “Late Show” where David Letterman tells Jon Stewart why Oprah Winfrey hates him follows.
“Late Show with David Letterman,” CBS Television
Oprah Winfrey interview on “Late Show” via HuffingtonPost.com