Sean Penn Secures Third Oscar, Ties All-Time Record for Male Acting Wins
Sean Penn has added a third Academy Award to his collection, tying the record for most Oscar wins by a male actor. He received the Best Supporting Actor award on Sunday, March 15, 2026, for his performance in Paul Thomas Anderson’s political drama, “One Battle After Another.” He shares the record with Jack Nicholson, Walter Brennan and Daniel Day-Lewis [The Hollywood Reporter].
A Commanding Performance in “One Battle After Another”
Penn’s portrayal of a seasoned power broker in “One Battle After Another” was lauded for its depth and nuance. The character navigates complex political landscapes, showcasing both influence and the weight of past experiences. Critics highlighted Penn’s ability to blend intensity with restraint, delivering a standout performance within the film’s ensemble cast [AP News].
Notable Absence from the Ceremony
Despite the win, Sean Penn did not attend the 98th Academy Awards ceremony. Kieran Culkin announced Penn as the winner, noting, “He couldn’t be here tonight, or he didn’t aim for to” [AP News]. This absence follows Penn’s decision to skip the Actor Awards and BAFTA Awards, where he likewise received the Best Actor in a Supporting Role honor [TV Insider].
A Complicated Relationship with Awards Shows
Sean Penn has a history of distancing himself from awards ceremonies. In 2023, he publicly considered donating his previous Oscars to Ukraine to be melted down for ammunition, though he ultimately gave one of his statuettes to Ukrainian President Volodymyr Zelenskyy [TV Insider]. He previously skipped the Oscars in 1996, 2000, and 2002 [TV Insider].
Previous Oscar Wins
This latest win marks Penn’s third Academy Award. He previously won Best Actor for his roles in Clint Eastwood’s “Mystic River” (2004) and Gus Van Sant’s “Milk” (2009) [AP News].
“One Battle After Another” and Penn’s Current Interests
In “One Battle After Another,” Penn plays Colonel Steven J. Lockjaw, an antagonist in the film. Penn has expressed a renewed interest in acting due to projects like this one, stating that he enjoys “being participating in something that is of your current interest, and with people who are surprising” [Town & Country Magazine]. He also maintains his passions for carpentry and surfing [Town & Country Magazine].