From Mystic River to One Battle After Another: Sean Penn’s Triple Oscar Journey

Sean Penn’s Oscar story began in 2004 and reached a remarkable new chapter in 2026, when his Best Supporting Actor win at the 98th Academy Awards gave him his third career Oscar. The win, for his performance in Paul Thomas Anderson’s One Battle After Another, came without Penn present at the Dolby Theatre. Presenter Kieran Culkin accepted the award with a humorous acknowledgment of the actor’s no-show.

Penn first won Best Actor for Mystic River and followed that with a second win for Milk in 2009. Two decades on, his third win in a supporting role demonstrates that Penn remains one of the most vital and versatile screen actors working today. He now ties Jack Nicholson, Walter Brennan, and Daniel Day-Lewis for the most acting Oscars ever awarded to a man.

His character in One Battle After Another — a militaristic figure whose obsessions lead him down a dark path — was considered one of the best performances of the year. Paul Thomas Anderson’s direction was equally lauded, earning him both the Best Director and Best Adapted Screenplay Oscars, his first in either category. It was a defining night for both the director and his film.

Host Conan O’Brien delivered an opening monologue that balanced comedy and cultural awareness. He drew laughs with a reference to artificial intelligence threatening to replace human hosts, a subject that has become increasingly real for those working in entertainment. His words carried genuine weight as he acknowledged difficult global realities while celebrating the power of cinema.

Michael B. Jordan’s Best Actor triumph in Sinners over Leonardo DiCaprio was another major result of the evening. The night belonged to multiple winners — but the story everyone was talking about was the winner who wasn’t there.