Sean Penn has won the Best Supporting Actor award at the 2026 Oscars for "One Battle After Another," making him the fourth man ever to claim three acting Oscars. This result feels almost inevitable after months of unprecedented chaos in this category. Penn emerged as the late frontrunner after victories at the equivalent awards from BAFTA and SAG-AFTRA, the two precursor groups with the most overlapping voting membership with the Academy. However, 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.
What's more, Penn didn't attend the Actor Awards or the BAFTAs – key campaign stops that left his momentum unseized upon. Consequently, one of the biggest questions going into the 2026 Oscars – especially if you're reading social media or tracking betting markets – was whether Penn would be in attendance at all. In the end, he didn't attend the show, with presenter Kieran Culkin accepting on his behalf.
Considered one of the greatest actors of his generation, Penn garnered widespread acclaim for his transformative villainous role in "One Battle" as Col. Steven J. Lockjaw, a vivid avatar of contemporary American authoritarianism. It's actually Penn's first Oscar for a supporting performance, having previously been recognized by the Academy for his lead roles 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 a recent cover story in The Hollywood Reporter about Del Toro, Penn spoke in awe about a special screening where he watched reels of career highlights featuring himself, Del Toro, and Leonardo DiCaprio.
"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."
