Sean Penn Doesn’t Need to Show Up to Rewrite Hollywood History

It has been suggested that Sean Penn is difficult. Complex. Uncompromising. His behavior at the 98th Academy Awards — winning Best Supporting Actor for One Battle After Another without attending the Dolby Theatre — did little to challenge that reputation. Penn’s third career Oscar, accepted on his behalf by a wry Kieran Culkin, tied the all-time male acting record shared by Jack Nicholson, Walter Brennan, and Daniel Day-Lewis. History was made; Penn was elsewhere.

Penn’s previous wins were for Best Actor in Mystic River and Milk — two performances that each seemed definitive at the time. His third, for a supporting role in a Paul Thomas Anderson thriller, shows that at no point in his career has Penn stopped taking on work that demands everything from him. His character in One Battle After Another — a fanatical, obsessive military officer — is precisely the kind of role Penn finds irresistible.

Director Paul Thomas Anderson celebrated the evening’s biggest win with both Best Adapted Screenplay and Best Director — his first Academy Awards. Anderson’s films have long been ranked among the finest of their era, and the Academy’s recognition arrived on a night that will be long remembered in the history of both the ceremony and his career. The response to his wins was one of sustained, genuine warmth.

Host Conan O’Brien balanced entertainment and substance throughout. His opening monologue hit all the right notes — topical humor about AI, sincere celebration of the nominees’ global diversity, and a framing of the ceremony as something beyond an industry event. With nominees from 31 countries and six continents, that framing felt entirely earned.

Michael B. Jordan defeated Leonardo DiCaprio for Best Actor in Sinners, completing a night of major results across all categories. Sean Penn may not have needed to show up to rewrite history — but his absence made the rewrite all the more vivid.