Paul Thomas Anderson’s Big Night Includes a Record Win for an Absent Sean Penn

Paul Thomas Anderson has waited a long time for his Oscar moment, and when it finally came at the 2026 Academy Awards, it came in spectacular fashion. His film One Battle After Another won Best Adapted Screenplay and Best Director for Anderson, while his lead actor Sean Penn claimed Best Supporting Actor — the third Oscar of Penn’s career, tying a record held by just three other male performers. The only dampener was Penn’s absence from the Dolby Theatre, leaving presenter Kieran Culkin to accept the trophy.

Penn’s three Oscars place him level with Jack Nicholson, Walter Brennan, and Daniel Day-Lewis in the most exclusive acting club in cinema. His first two wins were both for Best Actor — for Mystic River and Milk — which makes this supporting win all the more unusual in the context of his career. Culkin, last year’s winner in the same category, handled Penn’s no-show with a characteristic dry wit.

The film itself is a darkly comic thriller in which Penn plays a fanatical military officer whose obsessions slowly consume him. Critics praised both the film and Penn’s performance lavishly during awards season. Anderson, whose other films include celebrated works across multiple decades, finally received the Academy’s recognition he had long been considered overdue.

Conan O’Brien hosted the ceremony and brought his signature self-deprecating humor to the proceedings. His joke about artificial intelligence potentially replacing him drew genuine laughter from the audience. He also set a reflective tone, noting that the nominees came from 31 countries, turning the Oscars into a global celebration of storytelling.

In the Best Actor race, Michael B. Jordan claimed the prize over Leonardo DiCaprio for his acclaimed performance as twins in Sinners. One Battle After Another’s dominance and Penn’s absent triumph made the 98th Oscars a night to remember.