In a mostly earnest, insightful and educational conversation about health, food noise, GLP-1s and the dangers of not recognizing obesity as a disease, Oprah Winfrey and Gayle King delivered some moments of levity as only best friends can do during a special appearance at 92nd Street Y.
The two appeared at New York’s cultural and community center Tuesday with King acting as moderator for a conversation that featured Winfrey and Dr. Ania M. Jastreboff discussing their new book, Enough: Your Health, Your Weight and What It’s Like to Be Free. As King noted at the top of the hourlong chat, 2026 marks a milestone 50th anniversary of meeting as friends in Baltimore, Maryland back in 1976. “We were 21 and 22, now we’re 71 and 71. [Oprah] is turning 72 soon.”
Winfrey, whose birthday is Jan. 29, drew laughs, cheers and gasps when she revealed just how many shots she downed in order to win a drinking contest in Santa Barbara, not far from her estate in Montecito. The topic of conversation came up after King recalled being at a Golden Globes party last weekend when she asked the bartender for a Shirley Temple. “The person next to me said, ‘Seriously?’ I go, ‘Seriously with extra cherries.’ I just don’t drink but you don’t drink now either.”
Winfrey confirmed that she’s off the sauce even though she “used to be a tequila girl.” King then prodded her to cite the number of shots she downed in one sitting. “There’s something in Santa Barbara called the Fiesta festival. People are out in the streets, and you’re drinking and having a good time. That’s the whole point. One night we had a drinking contest and I won with 17 shots,” Winfrey confirmed. While she didn’t name names of who she drank under the table, King did have more to say: “Don’t applaud that. That’s terrible.”
King praised her best friend at other times during the revelatory chat. “This is the most open and honest conversation I’ve ever heard her have about her weight, which, by the way, is nobody’s business,” King said of Winfrey, who generated countless headlines when she revealed she turned to GLP-1s to help with a nearly lifelong battle with obesity.
“The bottom line is this, no amount of fame, wealth, success, attention can substitute for your biology,” Winfrey said. “I’m here now telling you there is a pill. There are medications. You can opt to use them or not use them. If you don’t use them or don’t want to use them, that’s really fine. But just know that the struggle doesn’t have to be the struggle that you’ve had, and if you are going to choose to lose weight by eating healthily and working out and the weight comes back, understand why it always comes back.”
Winfrey’s movie career came up when she recalled the promotional cycle for Jonathan Demme’s 1998 film in which she starred opposite Danny Glover. “I was promoting this movie, Beloved, which y’all did not go to see. One person went to see it in this room,” she said jokingly. “Anna Wintour wanted to do a cover. I remember just as she was walking out, she goes, ‘You know, you have to lose 20 pounds.’ I said, ‘OK, I’m gonna do it.’ And I felt really great losing that 20 pounds. I’m telling you, when they brought me the first Polaroid of that Vogue cover, I cried. I cried because I thought the very idea that somebody who had suffered so much from all the weight issues would be on the cover of Vogue.”
King said she still recalled the cover line: “A Major Movie, An Amazing Makeover.”
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