Sean Penn, the only actor to have won three Academy Awards in the modern era, says skipping the 98th Oscars ceremony — where he claimed his third statuette — turned out to be a genuine pleasure. Speaking Friday at the Tribeca Film Festival in a conversation with CNN anchor Kaitlan Collins, Penn said that watching the show from home let him experience the ceremony without the social dread that has shadowed him throughout his career.
Penn won his third Oscar in March for Best Supporting Actor, playing the repressed oppressor Col. Steven J. Lockjaw in Paul Thomas Anderson’s Best Picture winner One Battle After Another. Presenter Kieran Culkin, who took home the same award a year earlier for A Real Pain, accepted the trophy on Penn’s behalf, quipping that Penn “couldn’t be here this evening, or didn’t want to.”
Penn told the Tribeca audience that the Academy Awards have “always represented social discomfort” to him. He said he won’t go anywhere to be with a designated group larger than eight people, describing anything beyond that as “anxiety and dread-provoking.” The problem, he explained, is geometry: a crowded room full of old friends becomes a series of thwarted conversations — a wave across the room, a promise to catch up, and then a sprint for the exit by evening’s end.
Penn attended the 2026 Golden Globes in January, where a photo of him smoking indoors became briefly viral, and Collins opened the Tribeca discussion with a joke about the image. That night apparently confirmed his decision to sit out the rest of the awards circuit. He said the One Battle After Another team supported the choice: “They know me, and they felt it was better for my mental health.”
Penn had previously won Best Actor for Mystic River in 2004 and Milk in 2009, and said the best he could muster on both occasions was relief. Skipping the ceremony this time broke the pattern. “I got to be excited watching the awards,” he said. “I really got to enjoy the Academy Awards for the first time.”
Penn was in Europe at the time of the ceremony — his plan was to visit Ukraine and meet with President Volodymyr Zelenskyy, a relationship that has defined much of his public life since Russia’s full-scale invasion in 2022. After Penn missed the ceremony, Zelenskyy called him “a true friend of Ukraine,” and a Ukrainian Railways official presented Penn with an Oscar-shaped award forged from war-damaged metal of a Ukrainian railcar.
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Penn also used the Tribeca stage to deliver a pointed verdict on selfie culture. “People should not do selfies with anyone ever,” he said. “It’s bad for you.”
