The 2026 Oscars Gave the World History and a Mystery: Where Was Sean Penn?

The 98th Academy Awards answered many questions on Sunday night — who would win Best Actor, whether Paul Thomas Anderson would finally claim his first Oscar — but left one conspicuously unanswered: where was Sean Penn? Penn won Best Supporting Actor for One Battle After Another, tying the all-time male acting record with his third career Oscar, and was simply not at the Dolby Theatre. Presenter Kieran Culkin collected the award and offered an explanation that was simultaneously honest and unhelpful: Penn either couldn’t or didn’t want to be there.
Penn’s three wins place him alongside Jack Nicholson, Walter Brennan, and Daniel Day-Lewis — the only other men to win three acting Oscars. His previous wins for Mystic River and Milk were two of the most celebrated Best Actor performances in recent history. His third win, for a supporting performance, adds a new dimension to one of the richest careers in modern cinema.
One Battle After Another gave Penn the role of a military officer undone by ideology, and his performance was called one of the finest of the year. Director Paul Thomas Anderson won Best Adapted Screenplay and Best Director for the same film — his first career Oscars after decades of acclaimed and previously unrewarded work. Anderson’s wins were received with enormous warmth by the room.
Conan O’Brien’s hosting was a bright spot in an already bright evening. His joke about AI eventually replacing human hosts was well-landed and timely. His celebration of the global diversity of the nominees — from 31 nations and six continents — gave the ceremony a genuinely international resonance. He managed the evening’s heavier moments with the same skill as its lighter ones.
Michael B. Jordan defeated Leonardo DiCaprio for Best Actor in Sinners, one of the evening’s biggest surprises. The 2026 Oscars offered records, upsets, and a mystery — and all three will keep the conversation going for a very long time.