Oprah Winfrey is a woman of many talents, and taking shots is one of them.
Winfrey and along with Gayle King appeared at the 92nd Street Y, where she was promoting her new book, Enough: Your Health, Your Weight and What It’s Like to Be Free. During the conversation, Winfrey revealed that she once drank 17 shots of tequila in a drinking context.
“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.
“Don’t applaud that. That’s terrible,” King added.King also praised Winfrey for being open about her weight-loss journey.
“This is the most open and honest conversation I’ve ever heard her have about her weight,” King said. “Which, by the way, is nobody’s business.”
“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. 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 then spoke about a pivotal moment that occurred when she starred in the film Beloved.
“I was promoting this movie, Beloved, which y’all did not go to see. One person went to see it in this room,” Winfrey laughed. “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 those 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.”
Winfrey and King also shared that 2026 is the 50th anniversary of their friendship. The two met inBaltimore, Maryland, in 1976.
“We were 21 and 22, now we’re 71 and 71,” King said. Oprah is turning 72 soon.”

