Paul Thomas Anderson brought one of his most ambitious and darkly funny films to the 98th Academy Awards, and One Battle After Another rewarded him and his cast with multiple Oscars. Sean Penn won Best Supporting Actor for his lead performance, claiming his third career Oscar and tying the record for male acting wins at the Academy Awards. Penn, however, was not present at the Dolby Theatre to receive his award, and presenter Kieran Culkin stepped in with a humorous remark.
Penn’s three wins place him with Jack Nicholson, Walter Brennan, and Daniel Day-Lewis — the only other men in history to have won three acting Oscars. Penn’s career trajectory at the Oscars is remarkable: Best Actor for Mystic River, Best Actor for Milk, and now Best Supporting Actor for One Battle After Another. Three wins across two decades of work is a record that will likely stand for many years.
Penn’s performance as a military officer driven by obsessive conviction was one of the most discussed of the awards season. Director Anderson matched Penn’s success, winning his first two Oscars — for Best Adapted Screenplay and Best Director — completing an extraordinary night for the film. Anderson’s wins were greeted with genuine warmth by an industry that has long admired his work without always rewarding it.
Conan O’Brien was the evening’s host and brought his characteristically dry and clever humor to the proceedings. His monologue touched on artificial intelligence and the future of entertainment before settling into a thoughtful celebration of international filmmaking. He highlighted nominees from 31 countries on six continents as evidence of how global cinema has truly become.
Michael B. Jordan won Best Actor for Sinners, defeating Leonardo DiCaprio in a surprise result. The 2026 Oscars delivered an evening full of headline moments — and their most enduring story was, fittingly, about a man who chose to write it from outside the room.
One Battle After Another Turns Into One Historic Night After Another for Penn and Anderson
