Summary of this article
Sean Penn won his third Academy Award at Oscars 2026.
He bagged the best supporting actor award for Paul Thomas Anderson's One Battle After Another.
However, Penn didn't attend the awards ceremony.
Sean Penn, 65, won the best supporting actor award at the 2026 Oscars for portraying Colonel Steven J. Lockjaw in Paul Thomas Anderson's One Battle After Another, joining the ranks of Meryl Streep and Ingrid Bergman, among others. This is his third Academy Award.
Penn previously won two Oscars for Best Actor at the Academy Awards — first for his role as Jimmy Markum in Clint Eastwood's 2003 crime drama Mystic River and another one for playing gay rights activist Harvey Milk in Gus Van Sant's 2008 biopic Milk.
Sean Penn wins Best Supporting Actor at Oscars 2026
Penn won the prize beating Delroy Lindo, Benicio Del Toro, Jacob Elordi and Stellan Skarsgård. He has become the fourth male actor to win three Oscars after Jack Nicholson, Walter Brennan and Daniel Day-Lewis.
He has three previous Oscar nominations for Dead Man Walking, Sweet and Lowdown and I am Sam.
Penn has previously lost the Critics Choice Award to Frankenstein’s Jacob Elordi and the Golden Globe to Sentimental Value’s Stellan Skarsgard. However, he has won the Actor Award and the BAFTA for his menacing role in PTA's political comedy.
Penn skipped the ceremony held at the Dolby Theatre in Los Angeles. “He couldn't be here tonight, or he didn't want to,” Kieran Culkin said after announcing Penn as the winner.
The Tree of Life star has skipped most of the awards ceremonies this season. He didn't turn up for the BAFTA Awards in February, nor did he attend the Golden Globes in Los Angeles in January, where he was nominated for Best Supporting Actor. He also missed the SAG's Actor Awards earlier this month, where he won Best Supporting Actor.
