Oscars 2026: Celebrates actor Sean Penn added another milestone to his celebrated career at the 98th Academy Awards, winning the Oscar for Best Supporting
Actor for his performance in One Battle After Another. With the win, Penn becomes only the fourth male actor in Oscar history to secure three Academy Awards. Despite the major achievement, Penn was notably absent from the ceremony and did not attend the event in person. The award was presented by Kieran Culkin, who acknowledged Penn’s absence while accepting the statuette on his behalf. Check Out Oscars 2026 FULL Winners List Here “Sean Penn couldn’t be here this evening - or didn’t want to, so I’ll be accepting the award on his behalf,” Culkin joked while presenting the trophy. The win marks Penn’s third Oscar overall. He previously won Best Actor for his performances in Milk and Mystic River, in 2009 and 2004 respectively. Over the course of his career, the actor has also received several other nominations at the Academy Awards.
Penn’s performance in One Battle After Another, directed by Paul Thomas Anderson, has been widely praised throughout the awards season. In the film, Penn plays the intimidating Colonel Steven J. Lockjaw in the epic revolutionary comedy, a role that helped him secure multiple honours in the lead-up to the Oscars. Earlier this season, Penn won the BAFTA Awards and the Actor Awards for the same performance. However, the actor did not attend either ceremony, continuing a pattern of frequently skipping major awards events.
He also made headlines at the Golden Globe Awards earlier this year when he briefly broke the venue’s no-smoking rule by lighting a cigarette during the ceremony. Despite the moment drawing attention, Penn ultimately lost the Supporting Actor prize that night to Stellan Skarsgård for Sentimental Value.
Although Penn has been nominated five times before this latest victory, he has skipped several of those ceremonies over the years. In past interviews, he has even joked about melting down his Oscar trophies to create bullets for Ukraine amid the ongoing conflict.
Throughout his career, Penn has earned nominations for films including Dead Man Walking, Sweet and Lowdown and I Am Sam.
