No Walk to the Stage, No Speech — Just Sean Penn’s Third Oscar and a Wry Joke

Some Oscar wins arrive wrapped in tears and gratitude. Sean Penn’s third arrived wrapped in a joke about his absence. Penn won Best Supporting Actor at the 98th Academy Awards for One Battle After Another, and when no one appeared from the wings, presenter Kieran Culkin stepped forward, accepted the trophy, and delivered a line about Penn’s deliberate or unavoidable non-attendance. The audience laughed, applauded, and moved on — though the moment lingered long after the credits rolled.

Penn now stands alongside Jack Nicholson, Walter Brennan, and Daniel Day-Lewis in the record books — four men who have each won three acting Oscars. Penn had previously won Best Actor for Mystic River in 2004 and Milk in 2009. His transition to the supporting category for his third win reflects a performer who has always served the story before serving his own profile.

One Battle After Another gave Penn one of his most demanding recent roles — a military officer so wedded to his ideology that it becomes his downfall. Paul Thomas Anderson directed and wrote the film, earning his first two Oscars on the same night for Best Adapted Screenplay and Best Director. Anderson’s wins were among the most warmly received of the evening, reflecting the deep affection the film community has for his work.

Conan O’Brien hosted with his characteristic intelligence and ease, opening with a joke about AI rendering human hosts obsolete and celebrating the international reach of the nominees. The 31 nations represented among the nominees were highlighted by O’Brien as evidence of cinema’s expanding global community. His hosting was both entertaining and emotionally grounded.

Michael B. Jordan triumphed in the Best Actor category for Sinners, defeating the widely favored Leonardo DiCaprio. The 2026 Oscars had everything — history, humor, drama, and one gloriously empty stage.