by Kitty Kelley
Jon Stewart appeared on The Late Show with David Letterman a few nights ago and Stewart asked Letterman why he was always feuding with Oprah. Letterman laughed but Stewart probed he who will not be probed until Letterman told him about the day he decided to have lunch on Oprah. Both were eating at different tables in the same restaurant. Letterman told the waiter that Oprah wanted to pick up the tab. Dave waved to her and she waved back so the waiter assumed it was legitimate. Dave left and Oprah got stuck with the bill.
Stewart giggled. “That can’t be right,” he said.
“Sure, that pissed her off,” said Letterman. “Not everyone likes horse play.”
True, Oprah is not one for pranks at her expense but that was not the only reason she didn’t speak to Letterman for sixteen years.
On May 2, 1989, the night after Oprah hosted a devil-worshipping show that almost capsized her career, she appeared on Letterman’s s how. She was unnerved by the comedian’s quirky manner. The interview was awkward throughout, although Letterman did not go near the subject of Oprah’s show the previous day in which she had introduced a deranged guest named “Rachel,” who said that her family worshipped the devil and made sacrificial offerings of babies.
“And this is a—does everyone else think it’s a nice Jewish family?” asked Oprah, introducing “Rachel’s” religion. “From the outside you appear to be a nice Jewish girl…”
“Rachel” allowed that “not all Jewish people sacrifice babies…”
“I think we all know that,” said Oprah. Then she added: “This is the first time I heard of any Jewish people sacrificing babies, but anyway—so you witnessed the sacrifice?”
The phones at Harpo jangled for hours with irate callers objecting to Oprah’s blithe acceptance of “Rachel’s” claims, but Oprah was not too concerned. The next night she appeared on Late Night with David Letterman in Chicago. Letterman, who may have been drinking more than coffee, had a rowdy audience which wasn’t all that impressed with Oprah. Things became uncomfortable when someone yelled, “Rip her, Dave.” Letterman grinned his gleeful gap-toothed grin and said nothing. Years later he said, “I think she resented the fact that I didn’t rise to the occasion and, you know, beat up on the guy. Which I probably should have, but I was completely out of control and didn’t know what I was doing.”
A couple nights later, Letterman told his audience that he felt ill because he had eaten four clams at Oprah’s restaurant, The Eccentric. That iced it. Oprah slammed the door on Letterman and did not open it for sixteen years.
The following year Letterman hosted the Academy Awards show and did a play on the names of Uma Thurman and Oprah Winfrey. “Uma, Oprah; Oprah, Uma” misfired and Oprah, highly sensitive to her public image, was incensed.
After she launched O, The Oprah Magazine in 2000, Letterman took another poke at her by announcing “the Top Ten Articles from Oprah’s New Magazine”:
No. 10 P,R,A and H, the four runner-up titles for this magazine.
No. 9 Do what I say or I’ll make another movie
No. 8 Funerals and meetings with the Pope: Occasions not to use “You go, Girl.”
No. 7 While you’re reading this, I made 50 million dollars.
No. 6 The night I nailed Deepak Chopra.
No. 5 The million-dollar bill: A convenience that’s long overdue.
No. 4 My love affair with Oprah, by Oprah.
No. 3 You suckers will never know what it’s like to live in a solid gold mansion.
No. 2 Ricki Lake’s home phone number and how she hates 3 a.m. calls.
No. 1 The time I had to wait 5 minutes for a skim half-decaf latte.
By then the world seemed to be divided into Opraholics and Winfreaks who wanted nothing more than to appear on The Oprah Winfrey Show. Among them was David Letterman, who started an “Oprah Log,” begging for an invitation. Oprah ignored him but he persisted. “It ain’t Oprah ‘til it’s Oprah,” he told his audiences night after night. Soon his fans began holding up signs in front of the Ed Sullivan Theater, in airports, and at football games: “Oprah, Please Call Dave.”
After eighty-two nights, Phil Rosenthal advised Oprah in the Chicago Sun-Times: “This is a call you have to make…. Every night… he is making you look like a humorless, self-important diva who spouts all kinds of New Age platitudes about forgiveness and positive thought but stubbornly clings to grudges. He’s not the one who looks bad in this. It’s a funny bit, and so long as you refuse to play, you’re the butt of it… You’re simply digging in your heels, being stubborn, petty and stupid.”
Oprah did not make the call. She was still steamed about Letterrman’s jokes over the years:
Top Ten Disturbing Examples of Violence on TV:
No. 6 Unknowing guests gets between Oprah and the buffet
Top Ten Least Popular Tourist Attractions:
No. 3 The Grand Ole Oprah
Top Ten Death-Defying Stunts Robbie Knievel Won’t Perform:
No. 8 Screwing up Oprah Winfrey’s lunch order
Top Ten Things You Don’t Want to Hear from a Guy in a Sports Bar:
No. 1 Oops—time for Oprah.
Top Ten Things Columbus would Say About American if he were alive Today:
No. 6 “How did you come to chose the leader you call Oprah?”
Top Ten Dr. Phil tips for Interviewing Oprah:
No. 4 Grovel
Rapprochement came on December 1, 2005 when Oprah finally agreed to appear on Letterman’s show and then allowed him to escort her to the Broadway premiere of The Color Purple, prompting People to surmise:
And now, ladies and gentlemen, the Top Ten Most Likely Reasons Why Oprah Winfrey Ended Her 16-year Rift with David Letterman and Agreed to Appear on His CBS Late Show:
No. 10 She is producing a Broadway musical, The Color Purple, across the street
Nos. 9-1 See No. 10
“At last our long national nightmare is over,” said The Kansas City Star.
Letterman behaved like a star struck schoolboy. “It means a great deal to me, and I’m just very happy you’re here,” he gushed to Oprah. “You have meant something to the lives of people.”
An estimated 13.5 million people stayed up to watch that night, giving Letterman his biggest audience in more than a decade. The next day Washington Post TV writer Lisa de Moraes observed: “Letterman had become that which he once mocked. An Opraholic.”
Grateful as Letterman was to be in Oprah’s good graces he did not remain her love puppet. When she publicly announced in 2006 that she and her best friend, Gayle King, were simply best friends and not gay lovers, she once again became fodder for his late night monologue: “I hear that and I go hmmmmmm….”
Not so long ago the National Enquirer ran a cover of Oprah looking haggard and bloated with a headline that blared: “Oprah’s Booze & Drug Binges! Fed Up Stedman Walks Out—For Good! She’ll Pay $150 Million to Buy His Silence.” This prompted the always cheeky Letterman to announce:
The Top Ten Signs Oprah Doesn’t Care Anymore:
No. 1 Her last three guests were Johnnie Walker, Jim Beam, and Jose Cuervo.
Letterman vs. Winfrey will never reach pay-per-view because these heavy weights know the limits. She is accustomed to genuflection and he can’t bend a knee—for long. But both know their so-called feud serves them well, especially when they appear together on Super Bowl commercials. So let’s stay tuned for the next roumd.
Cross-posted from Huffington Post