Sean Penn has joined the most exclusive club in Hollywood. By winning Best Supporting Actor for his role in One Battle After Another, he became only the fourth male performer to win three acting Oscars, placing him alongside Daniel Day-Lewis, Jack Nicholson, and Walter Brennan in the pantheon of most-decorated actors. And he couldn’t be bothered to show up.
Penn was nowhere to be found when his name was called at the 98th Academy Awards. Instead, presenter Kieran Culkin—himself a recent Emmy winner for his work in Succession—delivered the news with a quip that captured the absurdity of the moment. “He couldn’t be here this evening or didn’t want to,” Culkin joked to the Dolby Theatre audience, shrugging with the perfect mix of respect and exasperation.
It’s not entirely surprising. Penn has never been one for the Hollywood glad-handing circuit. He famously skipped the 2009 Oscars when he won Best Actor for Milk, choosing instead to attend a humanitarian event in Haiti. He has spent more time in recent years focused on political activism and journalism than on the awards circuit, interviewing dictators for documentaries and conducting clandestine meetings with drug lords for Rolling Stone. The Oscar stage probably feels small compared to the world stage where Penn prefers to operate.
But his absence couldn’t diminish the achievement. Penn won for playing a racist soldier determined to join a secret society in Paul Thomas Anderson’s political thriller—a role that required him to tap into the kind of toxic masculinity and ideological fervor that he has spent his off-screen life fighting against. It’s the kind of contradiction that defines Penn’s career: the humanitarian who plays villains, the peace activist who excels at portraying violence.
His first two Oscars came for Mystic River (2003) and Milk (2008), performances that showcased his intensity and his ability to disappear into characters who exist on the margins of society. This third win, coming nearly two decades after his last victory, proves that Penn hasn’t lost his edge even as he approaches his mid-60s. The Academy clearly respects his commitment to the craft, even if they can’t always count on him to sit through four hours of ceremonies to collect the hardware.
The One Battle After Another cast took the stage to accept the award on his behalf, with Anderson acknowledging Penn’s contribution to the ensemble. It’s likely Penn will pick up the statuette from his agent’s office next week, or perhaps it will be mailed to whatever location he currently calls home—possibly a boat off the coast of Haiti, or a hotel room in Ukraine, or wherever his next journalistic adventure takes him.
Three Oscars. Two no-shows (at least). Sean Penn remains Hollywood’s most elusive superstar, collecting trophies the way some people collect parking tickets—acknowledging their existence but not letting them dictate his schedule.
See the performance that won it all—watch One Battle After Another and witness Sean Penn at the height of his powers, even if he won’t show up to accept the accolades.
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