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.
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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
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