Sean Penn’s Three Oscars Tell the Story of a Career Like No Other

The number three carries special weight in the history of the Academy Awards. It is the maximum number of acting Oscars any male performer has ever won, and until Sunday night, only Jack Nicholson, Walter Brennan, and Daniel Day-Lewis had reached it. Sean Penn joined them at the 98th ceremony, winning Best Supporting Actor for One Battle After Another to claim his third career Oscar. And like Penn himself, the moment was anything but conventional — he wasn’t there.

Presenter Kieran Culkin stepped in with characteristic ease, collecting the award and observing with dry humor that Penn had chosen not to attend or simply couldn’t. The crowd moved from confusion to laughter to applause in the space of a few seconds. Penn’s previous wins — Best Actor for Mystic River and Milk — were attended and celebrated. This one was celebrated without him.

One Battle After Another gave Penn the role of a deeply ideological military officer whose certainty ultimately becomes his ruin. The performance drew lavish critical praise and was widely considered one of the defining acting achievements of the year. Paul Thomas Anderson directed and wrote the film, and he was rewarded with both Best Adapted Screenplay and Best Director honors — the first Oscars of his career, and a recognition that the industry embraced warmly.

Conan O’Brien hosted the evening with poise and comedy, opening with a joke about AI threatening human employment in entertainment before pivoting to a celebration of cinema’s global reach. He noted that nominees came from 31 nations on six continents, framing the Oscars as a ceremony that now truly belongs to the world. His performance as host was praised for its balance of humor and heart.

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