Photo by Harald Krichel / Wikimedia Commons (CC BY-SA 3.0)
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Sean Penn became only the fourth male actor in Academy history to win three acting Oscars on Sunday night, but the milestone came with a twist — he wasn’t there to witness it in person. Penn’s Best Supporting Actor win for One Battle After Another was accepted by presenter Kieran Culkin, who stepped in with a witty remark about Penn’s apparent disinterest in attending. The moment briefly disrupted the ceremony’s flow before the audience broke into warm applause.
Penn’s record-tying achievement places him alongside Walter Brennan, Jack Nicholson, and Daniel Day-Lewis — three of the most iconic performers in Hollywood history. He previously won Best Actor for Mystic River in 2004 and again for Milk in 2009. Each win came for an entirely different kind of performance, illustrating the full range of Penn’s talent.
One Battle After Another, the Paul Thomas Anderson film at the center of Penn’s latest win, tells the story of a military officer undone by his own obsession. Anderson himself had a career-defining night, finally claiming his first Oscar trophies — for Adapted Screenplay and Best Director. The film’s success confirmed Anderson’s place among the very best filmmakers working today.
The 98th Oscar ceremony was hosted by comedian and talk show legend Conan O’Brien, who used his opening remarks to address both the humor and the gravity of the moment. He made a pointed joke about artificial intelligence replacing human hosts, a nod to the existential anxieties currently gripping Hollywood. He also celebrated the diversity of the nominees, representing 31 countries around the world.
Best Actor went to Michael B. Jordan for his celebrated twin performance in Sinners, marking a significant upset over the widely favored Leonardo DiCaprio. The 2026 Oscars will be remembered as a night of surprises, records, and one very conspicuous empty chair.
