Penn’s Record Win Adds a New Chapter to an Extraordinary Oscar Legacy

Sean Penn added a remarkable postscript to his career on Sunday night at the 98th Academy Awards, winning Best Supporting Actor for One Battle After Another and tying the all-time record for acting wins among male Oscar honorees. Penn, who did not attend the ceremony at the Dolby Theatre, had his award collected by presenter Kieran Culkin, who quipped about the actor’s mysterious absence to the delight and mild bewilderment of the crowd.

The win makes Penn one of only four men in history — along with Jack Nicholson, Daniel Day-Lewis, and Walter Brennan — to win three acting Oscars. His first two came in the Best Actor category, for Mystic River in 2004 and Milk in 2009. Now crossing into Best Supporting Actor, Penn has proven his flexibility and commitment to character over category.

Penn’s performance in One Battle After Another, as a militaristic officer who cannot see beyond his own doctrine, was called one of the year’s finest by critics. Paul Thomas Anderson, who directed and adapted the screenplay, walked away with two Oscars of his own — Best Director and Best Adapted Screenplay — a double victory that finally matched his critical standing with official Academy recognition.

Host Conan O’Brien used the evening to explore both humor and meaning. He opened with a monologue that poked fun at AI while acknowledging Hollywood’s genuine fears about technological displacement. He also spoke warmly about the global dimension of the ceremony, noting that nominees came from 31 countries spread across six continents.

Michael B. Jordan’s Best Actor victory for Sinners over Leonardo DiCaprio was among the other headline results. But the story that will outlast all others from the 2026 Oscars is the tale of Sean Penn — three-time winner and one-time no-show.