Three names dominated the conversation at the 98th Academy Awards: Sean Penn, Paul Thomas Anderson, and Michael B. Jordan. Penn won his record-tying third Oscar as Best Supporting Actor for One Battle After Another. Anderson won his long-overdue first two Oscars for the same film. And Jordan won Best Actor for Sinners, defeating Leonardo DiCaprio. It was a night that reshuffled the record books and surprised even those most familiar with Hollywood’s annual awards ritual.
Penn’s three Oscars now tie him with Jack Nicholson, Walter Brennan, and Daniel Day-Lewis, the previous co-holders of the male acting record. Despite the magnitude of the achievement, Penn was not present at the Dolby Theatre when his name was called — presenter Kieran Culkin accepted on his behalf with a dry and well-received quip about Penn’s absence. Penn’s previous wins were for Best Actor in Mystic River and Milk.
One Battle After Another gave Penn his most challenging and demanding recent role as an obsessive military officer. Paul Thomas Anderson crafted the film with the same meticulous care that defines all of his work, and the Academy rewarded that effort with both Best Director and Best Adapted Screenplay. Anderson’s double win closed the chapter on one of the longer award droughts for an acclaimed filmmaker in recent memory.
Conan O’Brien hosted with style, bringing humor and cultural awareness to his opening monologue. He joked about being replaced by an AI, celebrated the global diversity of the nominees, and framed the evening as a cause for optimism in a time of difficulty. His observation about 31 nations being represented among the nominees was one of the night’s more poignant moments.
Michael B. Jordan’s Best Actor win for Sinners was a genuine highlight of an already crowded evening. The 2026 Oscars will be studied for their record-breaking results and their reminder that the best nights in Hollywood often come with a twist.