No Actor Has Won More Oscars Than These Four Men — and Sean Penn Just Joined Them

For the fourth time in Academy history, a male actor has won three Oscars for acting. This time it is Sean Penn, who claimed Best Supporting Actor at the 98th Academy Awards for his role in One Battle After Another. Penn joins Jack Nicholson, Walter Brennan, and Daniel Day-Lewis in an exclusive club of performance excellence, though the newest member was not present at the Dolby Theatre to celebrate the moment in person.

Presenter Kieran Culkin accepted the award on Penn’s behalf, joking that the winner had chosen not to be there or simply couldn’t make it. Penn’s previous wins — Best Actor for Mystic River in 2004 and Milk in 2009 — were both attended, making his absence this time around more surprising to those in the audience. His first two wins established him as a generational talent; the third makes him a legend.

In One Battle After Another, Penn gives a performance described by critics as simultaneously terrifying and deeply human. He plays an obsessive military officer whose certainty about the world ultimately becomes his greatest weakness. Director Paul Thomas Anderson matched Penn’s success by winning his first-ever Oscars for Adapted Screenplay and Best Director, bringing his long-admired work official Academy recognition at last.

Comedian Conan O’Brien hosted the ceremony and brought a sharp wit to the proceedings. He opened with a joke about being “the last human host” before AI takes over, resonating strongly in an industry increasingly engaged with questions about automation and creativity. The international representation among nominees — 31 countries, six continents — gave the evening a genuinely global dimension.

Michael B. Jordan won Best Actor for Sinners, his portrayal of twin brothers earning him the prize over Leonardo DiCaprio. The night belonged to many winners, but the story that will endure is that of Sean Penn and an empty stage.