In the Year of One Battle After Another, Sean Penn Became a Three-Time Oscar Champion

The film that defined the 98th Academy Awards was Paul Thomas Anderson’s One Battle After Another — a darkly comic thriller that swept key categories and gave its lead actor one of the most historic wins in Oscar history. Sean Penn claimed Best Supporting Actor for his performance, earning his third career Oscar and tying the all-time record for male acting wins shared by Jack Nicholson, Walter Brennan, and Daniel Day-Lewis. Penn was not at the Dolby Theatre for the moment, and presenter Kieran Culkin accepted on his behalf.
Penn’s Oscar wins now span more than two decades: Best Actor for Mystic River in 2004, Best Actor for Milk in 2009, and now Best Supporting Actor for One Battle After Another. That progression — from celebrated lead roles to a deeply committed supporting performance — reflects a performer who has never allowed commercial expectations to dictate his choices. Penn has always sought the work that challenges him most.
His character in the film — a military officer undone by his own ideological extremism — was one of the most discussed acting achievements of the awards season. Anderson’s direction gave the film its dark wit and tonal precision, and he won both Best Adapted Screenplay and Best Director to match Penn’s win. Anderson’s first-ever Oscars came after a career widely regarded as one of the most significant in contemporary American cinema.
Host Conan O’Brien was a confident and well-received presence throughout the evening. He opened with a joke about AI making human hosts obsolete, touched on the global nature of the nominees, and framed the evening as a celebration of storytelling across cultures. With nominees from 31 nations and six continents, the ceremony reflected the truly international character of modern filmmaking.
Michael B. Jordan won Best Actor for Sinners, defeating Leonardo DiCaprio. In a night defined by the dominance of One Battle After Another, Penn’s absent triumph was both the film’s greatest achievement and the ceremony’s most memorable moment.