Sean Penn Ties All-Time Record for Male Acting Wins at Oscars 2026
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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.
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Share on Facebook Share on X Google Preferred Share to Flipboard Show additional share options Share on LinkedIn Share on Pinterest Share on Reddit Share on Tumblr Share on Whats App Send an Email Print the Article Post a Comment 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. Related Stories Movies Miles Caton Joined by Misty Copeland, Shaboozey and More for "I Lied to You" Oscars Performance Movies Amy Madigan Receives Standing Ovation for 'Weapons' Win, Thanks Ed Harris and "All the Dogs" 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 thir...
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