Director Anderson and Actor Penn Rewrite Oscar History on the Same Night

The 98th Academy Awards was a landmark evening for two men above all others: Paul Thomas Anderson and Sean Penn. Anderson won his first Oscars — for Best Adapted Screenplay and Best Director — for One Battle After Another, a film he spent years developing with the passion and precision that defines his work. Penn, the film’s lead actor, won Best Supporting Actor for the same film, claiming his third career Oscar and tying the all-time male acting record. One man was in the room; the other was not.

Penn’s absence was acknowledged by presenter Kieran Culkin, who accepted the award with a dry remark about the winner’s decision to stay away. Penn’s three wins now place him alongside Jack Nicholson, Walter Brennan, and Daniel Day-Lewis — the only other male actors in history to win three acting Oscars. His previous victories came for Best Actor in Mystic River and Milk.

Penn’s character in One Battle After Another — a military officer whose extremist convictions drive him toward ruin — was universally praised as one of the finest performances of the year. Anderson’s direction gave the film its dark comedic texture and moral ambiguity, and his wins were received with visible emotion from a room that has long admired his filmmaking without always formally rewarding it.

Conan O’Brien presided over the ceremony with wit, intelligence, and genuine warmth. His opening monologue touched on the specter of artificial intelligence in entertainment and celebrated the unprecedented diversity of the nominees. With participants from 31 countries and six continents, the 2026 Oscars were framed as a global event rather than a parochial industry celebration.

Michael B. Jordan won Best Actor for Sinners, defeating Leonardo DiCaprio in the evening’s most fiercely contested race. The night belonged to Penn and Anderson — but the memory of Penn’s empty seat will outlast almost everything else.