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Sean Penn Wins His Third Oscar, Tying the Record for Most Academy Awards Won by a Male

Sean Penn ties the all-time male acting Oscar record with three wins but was absent from the ceremony, reportedly traveling to Ukraine amid ongoing conflict, sources said.

  • On Sunday, Sean Penn won the Academy Award for best supporting actor for One Battle After Another, announced by presenter Kieran Culkin onstage. The win marks his third Oscar, reported as the headline result of the night.
  • After a long awards season, Penn emerged as a front-runner after victories at the BAFTA Awards and the Actor Awards, whose voters overlap heavily with the Academy.
  • On stage, Culkin joked 'Sean Penn couldn’t be here this evening—or didn’t want to,' after accepting the award for Penn, who was not in attendance.
  • With the statuette, Sean Penn joins a rare club of three-time winners, and One Battle After Another, with 13 nominations, gains reinforced awards-season stature from the win.
  • The New York Times reported Penn was traveling to Europe en route to Ukraine, explaining his absence while highlighting his 2022 Oscar gift to President Volodymyr Zelensky.
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150 Articles

Center

The Oscar Award winner, Sean Penn, has resigned from the ceremony to visit Kievul Sean Penn, who won the Oscar award for the best player in the second role for the "One Battle After Another" film, is in Ukraine to...

·Romania
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Lean Left

American actor Sean Penn, who won his third Oscar at a ceremony he was absent from on Sunday, is in Kyiv to "support Ukraine" and should be received Monday by President Volodymyr Zelensky, told AFP a senior Ukrainian official.

·Montreal, Canada
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Lean Left

Sean Penn won his third Oscar, but didn't show up to the gala. It would have been a bigger miracle if he had.

·Helsinki, Finland
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Town & Country broke the news in on Sunday, March 15, 2026.
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