Sean Penn has won best supporting actor at the 2026 Oscars for One Battle After Another, putting him in esteemed company as just the fourth man ever to win three acting Oscars.
The result feels relatively expected after months of unusual chaos in the category. Penn emerged as the late-breaking front-runner after winning the equivalent awards from BAFTA and SAG-AFTRA, the two precursor groups with the most key overlaps in voting membership with the Academy. But Penn had previously lost the Critics Choice Award to Frankenstein’s Jacob Elordi and the Golden Globe to Sentimental Value’s Stellan Skarsgard, both of whom were also nominated for the Oscar.
And Penn didn’t show up to the Actor Awards or the BAFTAs — key campaign stops that left the momentum unseized upon. Accordingly, one of the biggest questions going the 2026 Oscars — at least if you’re reading social media or tracking betting markets — was whether Penn would be in attendance at all. He ultimately did not attend the show, with presenter Kieran Culkin accepting on his behalf.
Considered one of the greatest actors of his generation, Penn drew wide acclaim for his transformative villainous turn in One Battle as Col. Steven J. Lockjaw, a vivid avatar for contemporary American authoritarianism. It’s actually Penn’s first Oscar for a supporting performance, having previously been recognized by the Academy for his lead turns in Mystic River and Milk. (His other nominations were all for lead roles too: Dead Man Walking, I Am Sam and Sweet and Lowdown.) With this third Oscar, he ties the all-time record for male acting wins, joining Jack Nicholson, Walter Brennan and Daniel Day-Lewis.
Penn was also nominated this year against Sinners scene-stealer Delroy Lindo, who was considered a wild card for an upset, and his One Battle After Another costar, Benicio Del Toro, who won several critics’ awards in the lead up to the big show. In The Hollywood Reporter’s cover story on Del Toro last month, Penn spoke in awe of a special screening where he watched reels of career highlights play for del Toro, Leonardo DiCaprio — and himself.
“There’s a part of you that never leaves the theater seat where you were 17,” Penn said. “You’re watching your heroes up there. And then, suddenly, you’re sitting next to people who’ve become that for someone else.”
See the star-studded red carpet arrivals here.
