A Night for the Records: Sean Penn, Michael B. Jordan, and a Triumphant Paul Thomas Anderson

The 98th Academy Awards was a landmark evening on multiple fronts. Sean Penn claimed his third Oscar for Best Supporting Actor in One Battle After Another, tying the male acting record shared by Jack Nicholson, Daniel Day-Lewis, and Walter Brennan. Paul Thomas Anderson won his first-ever Oscars for directing and writing the same film. And Michael B. Jordan beat out Leonardo DiCaprio for Best Actor in Sinners. The only thing missing from the celebration was Sean Penn himself.
Penn skipped the Dolby Theatre ceremony, leaving presenter Kieran Culkin to accept on his behalf. Culkin’s comment that Penn either couldn’t or didn’t want to be there briefly upended the ceremony’s smooth flow before eliciting laughter and applause. Penn’s absence added an eccentric footnote to what was already a historically significant win.
In One Battle After Another, Penn plays a militaristic figure driven beyond the boundaries of reason, a role praised universally as among his finest. Anderson’s direction gave the film a dark, comedic edge that set it apart from other awards-season fare. Anderson’s two Oscars — for Best Adapted Screenplay and Best Director — were warmly received by a crowd that has long admired his work.
Host Conan O’Brien delivered a sharp and warm performance, starting with a joke about being displaced by artificial intelligence and closing his opening with a genuine celebration of global cinema. He noted that the nominees represented 31 countries on six continents — an unprecedented level of international representation. His tone was perfectly calibrated for a ceremony balancing industry glamour with real-world concerns.
Michael B. Jordan’s victory in Sinners was arguably the biggest surprise of the evening, given the widespread expectation that Leonardo DiCaprio would prevail. But in a night full of surprises, the biggest was the man who made history and wasn’t there to see it.