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Actor Sean Penn walks down a street in Kyiv on Monday.GENYA SAVILOV/AFP/Getty Images

Sean Penn has built one of the most decorated careers in contemporary acting, and he has added another Oscar to the list.

On Sunday, Penn won the Academy Award for best supporting actor for his performance in Paul Thomas Anderson’s political drama One Battle After Another. He delivered a commanding portrayal of a seasoned power broker navigating the shifting loyalties and ideological battles at the centre of the film.

Penn, 65, did not attend the Oscars. The win is Penn’s third Academy Award.

“He couldn’t be here tonight, or he didn’t want to,” Kieran Culkin said after announcing Penn as the winner.

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Kieran Culkin presents the award for best performance by an actor in a supporting role during the Oscars on Sunday.Chris Pizzello/The Associated Press

It’s not the first time Penn has been an Oscars no-show. He’s previously skipped the show three times when he was nominated for Dead Man Walking in 1996, Sweet and Lowdown in 2000 and I Am Sam in 2002. Penn also bowed out from attending the BAFTAs and Actor Awards this year.

Mykola Serha, founder and leader of Cultural Forces, an informal association of Ukrainian servicemen from creative professions formed to support military personnel through arts and culture, told The Associated Press on Monday that Penn is in Ukraine.

Ukrainian President Volodymyr Zelensky posted a photo of him meeting with Penn on his social media Monday with the message “Because of you, Sean, we know what a true friend of Ukraine is. You have been with Ukraine since the first day of the full-scale war. And today as well. And we know that you will continue to stand with our country and our people.” In 2022, Penn gave one of the Oscar statuettes to Zelensky.

'One Battle After Another' won best picture at the Academy Awards, leading a haul of six trophies. Michael B. Jordan won the award for best actor for 'Sinners' and Jessie Buckley took best actress for 'Hamnet.'

Reuters

In One Battle After Another, Penn plays a calculating strategist named Col. Steven J. Lockjaw whose decades of experience in political movements give him both influence and scars. His character carries the weight of past victories and failures, offering sharp insights while quietly pulling strings behind the scenes. The performance blends Penn’s trademark intensity with moments of restraint, delivering a standout performance among the film’s talented ensemble.

Penn did attend when he previously won two Academy Awards for best actor for Clint Eastwood’s 2003 crime drama Mystic River and for portraying San Francisco politician and LGBTQ rights pioneer Harvey Milk in Gus Van Sant’s 2008 biopic Milk.

The actor first gained attention in the 1980s, with films including Fast Times at Ridgemont High, but quickly established himself as one of Hollywood’s most fearless dramatic actors. Over the decades he has delivered acclaimed performances in films such as Dead Man Walking, Carlito’s Way, The Thin Red Line, and I Am Sam.

His performance in One Battle After Another adds another acclaimed role to a career defined by intense and transformative performances.

Other nominees included fellow One Battle cast member Benicio Del Toro and Delroy Lindo for Sinners, Jacob Elordi for Frankenstein and Stellan Skarsgård for Sentimental Value.

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