Oprah Winfrey reveals she drank 17 shots to win a drinking contest

In a rather serious, 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 during a special appearance at the 92nd Street Y.

The two appeared at the New York Cultural and Community Center on Tuesday, with King serving as moderator of a conversation featuring Winfrey and Dr. Ania M. Jastreboff discussing their new book, Enough: Your Health, Your Weight, and What It Means to Be Free. As King noted at the start of the hour-long conversation, 2026 marks the 50th anniversary of our friends meeting in Baltimore, Maryland, in 1976. “We were 21 and 22, now we’re 71 and 71. (Oprah) will be 72 soon.”

Winfrey, whose birthday is Jan. 29, drew laughs, cheers and gasps when she revealed how many shots she drank to win a drinking contest in Santa Barbara, not far from her Montecito estate. The topic of conversation came up after King recalled attending a Golden Globes party last weekend when she asked the bartender for a Shirley Temple. “The person next to me said, ‘Seriously? I say, “Seriously, with extra cherries.” I just don’t drink, but you don’t drink now either.

Winfrey confirmed that she is no longer into the sauce even though she “was a tequila girl.” King then prompted her to cite the number of shots she downed in a single session. “There’s something in Santa Barbara called the Fiesta festival. People are in the streets, we’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. Although she didn’t name the names of the people she drank under the table, King had something else to say: “Don’t applaud this. It’s terrible.”

King praised her best friend at other times during the revealing conversation. “It’s the most open, honest conversation I’ve ever heard her have about her weight, which, by the way, is nobody’s business,” King said of Winfrey, who made countless headlines when she revealed she had turned to GLP-1s to help her in her nearly life-long battle with obesity.

“Ultimately, no amount of fame, wealth, success or attention can replace your biology,” Winfrey said. “I’m here now to tell you that there is a pill. There are medications. You can choose to use them or not to use them. If you don’t use them or don’t want to use them, that’s fine. But just know that the struggle doesn’t have to be the struggle that you had, and if you choose to lose weight by eating healthy and exercising and the weight comes back, understand why it keeps coming back.”

Winfrey’s film career came to light when she recalled the promotional cycle for Jonathan Demme’s 1998 film in which she starred alongside Danny Glover. “I was promoting this film, Belovedthat you haven’t gone to see. One person went to see it in this room,” she said jokingly. “Anna Wintour wanted to do a cover. I remember as she was coming out, she said, “You know, you need to lose 20 pounds.” I said, ‘OK, I’ll do it.’ And I felt really good losing those 20 pounds. I tell you, when they brought me the first Polaroid of this Vogue cover, I cried. I cried because I thought the very idea that someone who had suffered so much from all these weight problems would be on the cover of Vogue.”

King said she still remembers the cover phrase: “A major motion picture, an incredible transformation.”