Sean Penn’s Third Oscar Win Is the Strangest and Most Memorable of His Career

Of Sean Penn’s three Academy Award wins, the third is almost certainly the most memorable — not for a speech, but for its glaring absence. Penn claimed Best Supporting Actor at the 98th Academy Awards for his role in the Paul Thomas Anderson film One Battle After Another, but the actor himself was not at the ceremony to receive it. Presenter Kieran Culkin stepped forward with a dry remark and collected the award to warm applause.

Penn’s career now stands in rarefied territory. With three Oscars to his name, he ties Jack Nicholson, Walter Brennan, and Daniel Day-Lewis for the most acting wins in Academy history among men. His earlier victories — for Mystic River in 2004 and Milk in 2009 — were already enough to cement him as one of his generation’s defining screen actors. This third win elevates him to a different plane entirely.

In One Battle After Another, Penn plays a military officer undone by zealotry and obsession — a role that critics unanimously praised for its psychological depth and physical discipline. The film gave director Paul Thomas Anderson his first Academy Awards for Best Director and Best Adapted Screenplay. Anderson’s double win capped an extraordinary night for a filmmaker many believe to be among the greatest of his era.

Conan O’Brien was a charismatic and thoughtful host, opening with a joke about being displaced by artificial intelligence and closing his opening remarks with a celebration of global storytelling. Nominees from 31 countries were present, reflecting how thoroughly international the conversation around cinema has become. His opening set a tone of warmth and measured optimism.

Best Actor went to Michael B. Jordan for Sinners, in which he played twin characters to critical acclaim, beating out Leonardo DiCaprio. The 2026 Oscars were rich in drama, history, and humor — perfectly embodied by Sean Penn’s very public, very conspicuous absence.