Hollywood Royalty Grows: Penn’s Third Oscar Places Him Among the All-Time Greats

The 98th Academy Awards may be best remembered as the night Sean Penn tied the all-time record for acting wins at the Oscars — while sitting somewhere that was decidedly not the Dolby Theatre. Penn claimed Best Supporting Actor for his role in One Battle After Another, making it three career Oscars to place alongside those of Jack Nicholson, Walter Brennan, and Daniel Day-Lewis. Presenter Kieran Culkin collected the award on his behalf and told the audience what most of them had already guessed: Penn hadn’t wanted to come.

Penn’s acting history with the Oscars is remarkable in its breadth. He won Best Actor in 2004 for Mystic River and again in 2009 for Milk, two performances that are widely considered among the finest of their respective years. His third win, this time in a supporting capacity, shows that Penn’s talent continues to operate at the very highest level of the craft.

One Battle After Another, the Paul Thomas Anderson film that earned Penn his latest honor, is a darkly humorous look at obsession, military culture, and moral rigidity. Anderson himself walked away with his first two Oscars — for Best Adapted Screenplay and Best Director — a remarkable double for a filmmaker whose entire catalog has long been regarded as among the finest in contemporary American cinema.

Conan O’Brien served as host and brought his usual blend of intelligence and playfulness to the evening. His opening monologue touched on the threat of artificial intelligence to human livelihoods in entertainment, before pivoting to a more optimistic framing of the evening as a global celebration. Nominees from 31 nations underscored that point.

Michael B. Jordan won Best Actor for his acclaimed dual performance in Sinners, outpacing Leonardo DiCaprio in one of the night’s marquee contests. The 2026 Oscars delivered much to celebrate — with the night’s biggest winner noticeably absent.