Sean Penn Ties Oscar Record Without Setting Foot in the Dolby Theatre

Sean Penn made history at the 98th Academy Awards by winning the Best Supporting Actor award for his powerful performance in Paul Thomas Anderson’s thriller One Battle After Another — all without being present at the ceremony. The seasoned actor, known for his habit of skipping award shows, left the Dolby Theatre audience momentarily baffled before presenter Kieran Culkin stepped in to accept the trophy on his behalf. Culkin quipped that Penn “couldn’t be here, or didn’t want to,” drawing laughter and applause from the crowd.

This was Penn’s third acting Oscar, a milestone that ties him with Hollywood legends Jack Nicholson, Walter Brennan, and Daniel Day-Lewis as the most decorated male actors in Academy history. His earlier wins came for Best Actor in Mystic River in 2004 and Milk in 2009, making this Supporting Actor win a fascinating addition to his already legendary career. No other male actor in history has won more than three acting Oscars.

Penn played an obsessed military officer in One Battle After Another, a darkly comic thriller that proved to be one of the most celebrated films of the awards season. The film also earned director Paul Thomas Anderson his first Oscar, winning both Adapted Screenplay and Best Director on the same evening. It was a landmark night for Anderson, whose career-long work finally received the Academy’s highest recognition.

The broader 2026 Oscar ceremony was hosted by comedian Conan O’Brien, who opened with a self-deprecating joke about being “the last human host” in an era increasingly shaped by artificial intelligence. O’Brien struck a tone of cautious optimism, noting that nominees came from 31 countries across six continents. Meanwhile, Leonardo DiCaprio lost the Best Actor race to Michael B. Jordan, who won for his dual performance in Sinners.

Penn’s no-show added an unusual but memorable chapter to Oscar history. His win will be remembered not just for the record it tied, but for the manner in which the moment unfolded — awkwardly, humorously, and entirely on his own terms.