No Oscar Has Ever Been Accepted Quite Like Sean Penn’s Third

There are acceptance speeches, there are tearful tributes, and then there is the moment at the 2026 Academy Awards when Sean Penn’s name was called and Kieran Culkin had to step in for him. Penn won Best Supporting Actor for One Battle After Another at the 98th Oscars — his third career win and a milestone in the history of the ceremony — but the winner was simply not there. Culkin’s joke about Penn’s absence turned confusion into laughter, and the moment became one of the most memorable in recent Oscar memory.

Penn’s three wins place him in company with Jack Nicholson, Walter Brennan, and Daniel Day-Lewis — the only other men in Academy history to win three acting Oscars. His previous victories were both for Best Actor: Mystic River in 2004 and Milk in 2009. This supporting win adds a new layer to his already extraordinary legacy.

One Battle After Another, the Paul Thomas Anderson film behind Penn’s win, is a darkly comic thriller in which Penn plays a zealous military officer. Anderson’s direction and screenplay both received Oscar recognition — his first awards ever — making the film one of the evening’s biggest winners overall. Anderson’s long awards-season journey finally ended at the summit.

Host Conan O’Brien was a confident and entertaining presence throughout the night. He opened with a joke about artificial intelligence making his own role obsolete, before pivoting to a more celebratory note about the diversity of nominees from 31 countries. His opening monologue balanced comedy and genuine reflection effectively.

Michael B. Jordan’s win for Sinners over Leonardo DiCaprio was one of the night’s biggest talking points. Between Jordan, Anderson, and Penn — present or otherwise — the 2026 Oscars managed to be simultaneously historic, surprising, and oddly funny.