Jack Nicholson, Walter Brennan, Daniel Day-Lewis — and Now Sean Penn

Sean Penn has joined the most rarefied company in Hollywood acting history. His Best Supporting Actor win at the 98th Academy Awards for One Battle After Another gave Penn his third Oscar, matching the career total of Jack Nicholson, Walter Brennan, and Daniel Day-Lewis — the only male actors to reach that mark before him. The achievement was rendered slightly surreal by Penn’s absence from the Dolby Theatre, prompting presenter Kieran Culkin to step in with a wry observation.
Penn’s prior Oscars were both for Best Actor — Mystic River in 2004 and Milk in 2009. His move into the supporting category for One Battle After Another reflects not only his creative range but also his willingness to subordinate his star power to the demands of the story. Director Paul Thomas Anderson crafted a film that gave Penn the role of a militaristic officer spiraling out of control — and Penn delivered.
Anderson’s own night was equally remarkable. He won both Best Director and Best Adapted Screenplay, his first-ever Oscar wins, making it a landmark evening for the filmmaker whose career has long been critically celebrated but previously unrecognized by the Academy. The film dominated the ceremony in a way few had predicted heading into the evening.
Conan O’Brien returned to hosting duties for the occasion, drawing on his distinctive brand of self-deprecating humor. His opening remarks touched on artificial intelligence, the meaning of storytelling in troubled times, and the global footprint of modern cinema. The presence of nominees from 31 countries was a central theme of his opening remarks.
In the most competitive category of the night, Michael B. Jordan took Best Actor for Sinners, edging past Leonardo DiCaprio’s widely praised performance. The 2026 Oscars were full of memorable outcomes, with Sean Penn’s distant triumph among the most talked-about of them all.