History Quietly Made as Penn Ties Oscar Record Without a Word

Perhaps the most unusual thing about Sean Penn’s third Oscar win is that no one — including Penn — said a word about it at the ceremony itself. Penn won Best Supporting Actor for One Battle After Another at the 98th Academy Awards while being absent from the Dolby Theatre. The moment was handled with good humor by presenter Kieran Culkin, who accepted the award and joked about the winner’s apparent disinterest in attending his own historic moment.

Penn now shares the record for most acting Oscars by a male performer with Jack Nicholson, Walter Brennan, and Daniel Day-Lewis, each of whom won three during their careers. His previous wins were for Best Actor in Mystic River and Milk, and his third win — in the supporting category — adds remarkable depth to a career already full of it. Few performers of any era can claim wins in multiple categories across multiple decades.

In One Battle After Another, Penn delivers a performance that critics have described as masterful — a portrayal of a military officer stripped of all self-awareness by his own ideological obsession. Director Paul Thomas Anderson’s work on the film was equally applauded, earning him his first Oscars for Best Adapted Screenplay and Best Director in a career spanning three decades of critical and cultural acclaim.

Conan O’Brien was an engaged and entertaining host, touching on the fear of artificial intelligence replacing human creatives while also celebrating the global diversity of the ceremony. With nominees from 31 countries, the 98th Oscars felt less like a Hollywood industry event and more like a genuine international gathering of cinema’s best.

Michael B. Jordan’s Best Actor win for Sinners was one of the night’s most celebrated moments, with Jordan edging out Leonardo DiCaprio in a tightly contested race. From Jordan’s win to Penn’s silent triumph, the 2026 Oscars offered something for everyone.