Sean Penn secured his third Oscar at the 98th Academy Awards, but his empty seat at the Dolby Theatre left many questioning his absence—at least those unfamiliar with his long-standing friction with the ceremony.
Penn was nominated for Best Supporting Actor for his portrayal of Colonel Steven J. Lockjaw in Paul Thomas Anderson’s One Battle After Another. Although he won, he wasn’t there to accept the trophy. Instead, last year’s winner Kieran Culkin stepped in to accept on his behalf.
“Sean Penn couldn’t be here this evening—or didn’t want to,” Culkin joked to the crowd. This wasn’t an isolated incident; the veteran actor also skipped the BAFTAs and the Screen Actors Guild Awards earlier this month, missing the chance to collect his wins in person.
While Penn hasn’t released an official statement, sources close to the actor told The New York Times that he had planned a trip to Ukraine as of last week. Whether he actually made the journey remains unconfirmed, but “ghosting” the Oscars is a familiar move for the 65-year-old. According to The Associated Press, Penn previously skipped the ceremony despite nominations for Dead Man Walking in 1996, Sweet and Lowdown in 2000, and I Am Sam in 2002.
His absence likely stems from his blunt view of the institution. He once criticized the Academy for what he called “extraordinary cowardice” in “limiting the imagination and different cultural expressions.” In another interview, he was even more direct: “I don’t get very excited about what we’ll call the Academy Awards.”
Beyond the scheduling, Penn has long questioned the weight given to these awards. He recently suggested that the Oscars should be viewed primarily as a television product rather than a true barometer of artistic merit.
His priorities have clearly shifted toward his humanitarian work. In 2023, he told Variety he would consider melting down his statuettes to support relief efforts in Ukraine. “I’ll give them to Ukraine,” he said at the time. “They can be melted down into bullets to shoot at the Russians.” Penn eventually made a more symbolic gesture, gifting his Milk Oscar to President Volodymyr Zelenskyy during the filming of his 2023 documentary, Superpower, which explored Zelenskyy’s rise to leadership.
This year’s win for Best Supporting Actor marks a new milestone in Penn’s career. While he previously attended the ceremonies to accept Best Actor honors for Mystic River and Milk, this is his first victory in the supporting category. For Penn, however, it seems the “Iron Oscar” he recently received from Ukrainian officials holds far more value than the gold one waiting for him in Hollywood.
With this latest win, Penn joins an elite circle of three-time acting Oscar recipients, a group that includes legends like Meryl Streep, Jack Nicholson, Daniel Day-Lewis, Ingrid Bergman, Frances McDormand, and Walter Brennan. Katharine Hepburn remains the all-time leader, holding the record with four acting trophies for her roles in Morning Glory, Guess Who’s Coming to Dinner, The Lion in Winter, and On Golden Pond.
It was a historic night for One Battle After Another, which dominated the ceremony with a six-award sweep. The film took home the top honors for Best Picture and Best Director, along with wins for Best Editing, Best Adapted Screenplay, and the Academy’s first-ever trophy for Best Casting.
While the film saw immense success, it wasn’t a clean sweep for the cast. Leonardo DiCaprio, who starred alongside Penn, was nominated for Best Actor but ultimately lost to Michael B. Jordan, who took home the category’s top prize for his performance in Sinners.