This article was curated by It’s That Part, where we highlight the truth in every fact—curated for deeper insight and critical reflection.
Oprah Winfrey is many things: a media icon, a billionaire and a cultural force. But based on one story she shared this week, she’s also the friend you didn’t realize could absolutely drink you under the table.
During an appearance at New York’s 92nd Street Y on Tuesday (Jan. 12), Winfrey shocked the crowd when she admitted she once won a Santa Barbara drinking contest after downing 17 shots. The confession landed like a punchline, sparking laughter and cheers, according to The Hollywood Reporter, until Gayle King, who was sitting beside her like the responsible best friend she is, quickly shut it down.
“Don’t applaud that,” King joked. “That’s terrible.”
The hilarious throwback surfaced during a mostly educational conversation about health, weight, and “food noise,” as King moderated a discussion featuring Winfrey and Dr. Ania M. Jastreboff about their new book, “Enough: Your Health, Your Weight and What It’s Like to Be Free”.
Early in the talk, King noted that 2026 will mark a major milestone; nearly 50 years of friendship, dating back to when they first met in Baltimore in 1976. “We were 21 and 22, now we’re 71 and 71,” King cracked, adding that Winfrey—whose birthday is Jan. 29—will turn 72 soon.
Their bestie bond showed up in the way only real best friends can pull off: warm teasing, quick honesty, and the comfort of knowing you can tell the truth in public because the person next to you isn’t going to let you rewrite history.
That’s how the drinking story came up. King recalled being at a Golden Globes party last weekend and ordering a Shirley Temple, only for someone nearby to react with a blunt “Seriously?” King said she didn’t flinch; she doubled down: “Seriously with extra cherries.”
The moment was funny, but it also opened the door to Winfrey’s own shift. While she said she doesn’t drink anymore, she acknowledged she “used to be a tequila girl,” before pointing back to Santa Barbara’s Fiesta festival, where, at least one night, she was determined to win.
And she did.
Winfrey’s 17-shot confession may have been the moment that got the biggest gasp, but the message underneath it was unmistakable: this chapter isn’t about proving anything. It’s about understanding the body, letting go of shame, and choosing freedom over the struggle.
