Eminem once missed his Oscar win for 8 Mile and later said he had been home watching television with his daughter. Whether Sean Penn had similarly domestic reasons for skipping the 98th Academy Awards is unknown, but his absence from the Dolby Theatre on the night he made Oscar history was impossible to overlook. Penn won Best Supporting Actor for One Battle After Another, with presenter Kieran Culkin collecting the award and offering a humorous explanation to the puzzled crowd.
The win was Penn’s third career Oscar, a number that ties him with acting icons Jack Nicholson, Walter Brennan, and Daniel Day-Lewis for the most wins by any male actor in Academy history. Penn had previously claimed Best Actor honors for Mystic River and Milk, in 2004 and 2009 respectively. Those two wins had already marked him as one of the greatest performers of his generation.
One Battle After Another, the Paul Thomas Anderson film that brought Penn his third award, is a darkly humorous exploration of military obsession. Penn’s portrayal of a rigid, fanatical officer was hailed by critics as fearless and transformative. Anderson himself had cause for double celebration, winning both Adapted Screenplay and Best Director — Oscars that had long eluded him despite decades of acclaimed work.
Conan O’Brien served as host for the evening and brought sharp comedic energy to the ceremony. His opening monologue touched on artificial intelligence, global anxiety, and the role of storytelling in difficult times. The diverse range of nominees — from 31 countries across six continents — underlined the broad global appeal of contemporary cinema.
Michael B. Jordan won Best Actor for his performance as twin characters in Sinners, beating out Leonardo DiCaprio. It was a night of unexpected outcomes, and Penn’s quiet, distant triumph felt oddly fitting for an actor who has always refused to play by the rules.
A Historic Third Oscar for Sean Penn, Who Was Watching From Somewhere Else
