Sean Penn: Three Oscars, Two Lead Wins, One Famous Absence

When the complete story of Sean Penn’s relationship with the Academy Awards is written, the 2026 ceremony will occupy an unusual chapter. Penn won Best Supporting Actor for One Battle After Another at the 98th Oscars, claiming his third career win and matching the all-time record for male acting wins — while being physically absent from the Dolby Theatre. Presenter Kieran Culkin accepted the award with a humorous explanation that delighted the audience.

Penn’s three Oscars now tie him with Jack Nicholson, Walter Brennan, and Daniel Day-Lewis, making him one of only four men to reach that total in the entire history of the Academy Awards. He earned his first two wins as Best Actor — for Mystic River in 2004 and Milk in 2009 — and this third win, in the supporting category, rounds out a career that has consistently challenged genre and convention.

His character in One Battle After Another is a dogmatic military man whose certainty becomes a form of self-destruction — and Penn brought every ounce of that complexity to the screen. Director Paul Thomas Anderson was recognized twice in the same evening for the film, winning Best Adapted Screenplay and Best Director. It was Anderson’s first Academy recognition of any kind and represented a historic moment for a filmmaker of his stature.

Conan O’Brien hosted the ceremony and brought a combination of wit, warmth, and topicality to his role. He joked about being the last human to host such an event before AI takes over, and took time to highlight the unprecedented diversity of the nominee pool, drawn from 31 countries worldwide. His performance as host was widely praised.

Michael B. Jordan took Best Actor for Sinners, beating Leonardo DiCaprio in a race many had expected DiCaprio to win. The 2026 Oscars produced a series of memorable results — with Penn’s record-tying, stage-absent win leading the conversation.