Sean Penn’s Award, Kieran Culkin’s Moment: The Strangest Podium Scene of 2026

There are Oscar moments that people replay for years, and the 2026 ceremony produced one that will be quoted in every Sean Penn retrospective ever made. Penn won Best Supporting Actor for One Battle After Another — tying the male Oscar record with his third career win — and was not present at the Dolby Theatre. Presenter Kieran Culkin, last year’s winner in the same category, accepted the trophy and explained to the audience, with entirely dry precision, that Penn either couldn’t be there or hadn’t wanted to come.

Penn’s three career Oscars now equal those of Jack Nicholson, Walter Brennan, and Daniel Day-Lewis. His previous wins were Best Actor for Mystic River in 2004 and Milk in 2009. This third win, in the supporting category, completes a body of Oscar recognition that is as varied as Penn’s approach to acting itself.

One Battle After Another, the Paul Thomas Anderson film behind Penn’s win, placed the actor in the role of a military figure consumed by his own zealotry. Critics uniformly praised the performance as one of the year’s finest. Anderson’s own wins — Best Adapted Screenplay and Best Director — were his first, completing a night that saw both the film’s director and star reach personal milestones of remarkable significance.

Host Conan O’Brien was in fine form throughout, using his opening monologue to reference artificial intelligence, global uncertainty, and the meaning of cinema in difficult times. He highlighted the 31 countries represented among the nominees and praised the ceremony’s expanding international character. His hosting was both entertaining and thoughtfully calibrated to the moment.

Michael B. Jordan’s Best Actor win for Sinners over Leonardo DiCaprio rounded out a night full of top-tier results. The strangest and most memorable image of the evening, however, belongs entirely to Kieran Culkin — standing alone at the podium holding someone else’s Oscar.