Sean Penn discovered a paradox that only a true Hollywood legend could stumble into: the year he actually won an Oscar was the year he finally enjoyed watching the Oscars by not going. For decades, he has been one of American cinema’s most intense and decorated actors, earning acclaim and multiple Academy Awards while remaining famously uneasy about fame, crowds, and the spectacle surrounding them. For someone who disappears so completely into characters, he has often seemed uncomfortable in rooms built to celebrate that transformation.

Skipping the ceremony this year, he believes was the first time the whole experience felt like entertainment rather than endurance.

Speaking at the Tribeca Film Festival, Sean Penn explained that the awards show environment has long made him uneasy. He described events like the Oscars as a source of social discomfort, saying large gatherings feel overwhelming and difficult to navigate.

“I won’t go anywhere to be with a designated group beyond eight people,” he said, adding that anything more quickly becomes “anxiety- and dread-inducing.”

Because his film One Battle After Another was in contention and ultimately won Best Picture, with Penn taking Best Supporting Actor, skipping the ceremony was not a casual choice. He said his collaborators on the film understood and supported his decision, noting that it was better for his mental health. Instead of attending, he traveled to Ukraine to meet President Volodymyr Zelenskyy during the telecast. Watching the broadcast later, Penn said he experienced something unfamiliar.

“Having only felt relief a couple other times, I got to be excited watching the awards,” he explained, adding that it was the first time he truly enjoyed the show. He contrasted that with his earlier wins for Mystic River and Milk, when the prevailing emotion was pressure rather than celebration.

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However, his other Hollywood colleagues did not miss the chance to poke fun at his nonchalant behaviour.

Regina Hall kept the conversation around One Battle After Another firmly in the comedy lane during an appearance on The Tonight Show Starring Jimmy Fallon. She joked that Sean Penn’s Best Supporting Actor win was “embarrassing” because of how aggressively he supposedly campaigned for it. Delivering the line deadpan, she quipped.

“You saw how hard he campaigned?” The humor worked because it flipped reality on its head. Penn is known for avoiding the awards circuit, and in this case, he did not attend the Oscars at all. Hall leaned further into the bit, joking that he was “everywhere” and “desperate,” even as the audience recognized the irony.

The joke gained another layer during the ceremony itself when Kieran Culkin accepted the award on Penn’s behalf. He noted that Penn “couldn’t be here… or didn’t want to,” reinforcing the actor’s long-standing distance from Hollywood rituals. Rather than criticism, the moment played as affectionate teasing about someone who refuses to follow the usual playbook.

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What do you think about Sean Penn’s decision to skip the Oscars and Regina Hall’s playful take on it? Let us know in the comments.