Oscar Actors: Penn, Sean–Wins Third Oscar, “One Battle After Another”

Sean Penn Joins Elite of Male Actors with 3 Oscars

The ‘One Battle After Another’ star joins Jack Nicholson, Walter Brennan and Daniel Day-Lewis as the most Oscar-winning male actors of all time, at three apiece.

The result feels relatively expected after months of unusual chaos in the category. Penn emerged as the 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 Sentimental Value’s Stellan Skarsgard, who was 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 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 Delroy Lindo, and his One Battle After Another costar, Del Toro, who won several critics’ awards in the lead up to the big show.

“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.”

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