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Sean Penn Wins Best Supporting Actor at Oscars 2026—But Doesn’t Go to the Ceremony

Sean Penn Wins Best Supporting Actor at Oscars 2026—But Doesn’t Go to the Ceremony

It’s one win after another (after another) for Sean Penn. The One Battle After Another star is now a three-time Oscar winner, taking home best supporting actor for his go-for-broke performance as creepy, corrupt would-be Christmas Adventurer Colonel Steven J. Lockjaw in Paul Thomas Anderson’s best-picture nominee.

“Sean Penn couldn’t be here this evening—or didn’t want to,” cracked Kieran Culkin, last year’s best-supporting-actor winner, after he announced the category onstage.

Although Penn received rave reviews and Oscar buzz for his performance as the villain of One Battle After Another after the film premiered in September, it was far from written in the stars that Penn would win in this category. He faced stiff competition from his fellow nominees: Frankenstein’s Jacob Elordi; Sentimental Value’s Stellan Skarsgård; Sinners’ Delroy Lindo; and his One Battle After Another costar Benicio Del Toro. Toward the beginning of the Oscar-campaign season, Penn’s pole position status faltered slightly when he lost the Critics Choice Award to Elordi and the Golden Globe to Skarsgård. But in the final weeks of the extra-long campaign season, Penn regained front-runner status, taking home best supporting actor at the BAFTAs and the Actor Awards, though he didn’t attend either. (Ironically, Penn did opt to attend the Globes, though he didn’t seem to mind the loss, as he was busy smoking a cigarette indoors during the ceremony.) Given One Battle After Another’s status as front-runner, with 13 nominations and a slew of precursor wins at the PGAs, DGAs, and Actor Awards, it seems that, in the end, it was always Penn’s Oscar to lose.

Penn’s storied career began with his portrayal of the surfer stoner Jeff Spicoli in Fast Times at Ridgemont High (1982). He won his first Oscar for leading actor in 2004 for playing a grieving father in Mystic River. Nearly five years later, Penn would take home another leading-actor Oscar, this time for playing San Francisco politician Harvey Milk in Gus Van Sant’s Milk. Now that Penn has a third Oscar under his belt, he joins a rarefied club of three-time acting-Oscar winners that includes Jack Nicholson, Daniel Day-Lewis, and Meryl Streep.

A fierce advocate of progressive causes and critic of the Trump administration, Penn previously said that he would be willing to smelt his first two Oscars if the Academy didn’t offer Ukraine’s president a platform at the ceremony.

See What the Oscars 2026 Nominees Wore to Their First Academy Awards

Steve Granitz/WireImage

Timothée Chalamet, 2018

In Berluti.

Watch the Vanity Fair Oscar Party livestream—hosted by Quenlin Blackwell, Jake Shane, and Brittany Broski—directly after the Academy Awards at youtube.com/vanityfair on Sunday, March 15 at 10:30 p.m. ET and 7:30 p.m. PT.

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Source: VanityFair | Read the Full Story…

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