The Academy Awards have had their share of winners who were not in the room when their names were called. In 2003, Eminem won Best Original Song for 'Lose Yourself' from 8 Mile. The rapper skipped the ceremony entirely and later revealed he was at home sleeping, never expecting to win. Two decades later, another Oscar night absence is drawing attention for a very different reason. This time, Sean Penn was absent from the ceremony to accept his Best Supporting Actor award, dedicating the moment instead to expressing his support for Ukraine.

Sean Penn made headlines this year for skipping the Academy Awards and traveling to Kyiv instead, where he met with Ukrainian President Volodymyr Zelenskyy. The now three-time Oscar winner chose to spend the moment showing support for Ukraine Zelenskyy later shared a message on X thanking the actor for standing by Ukraine since the first day of the full-scale invasion.

This visit was not Penn’s first trip to Ukraine. He first arrived on February 24, 2022, the very day Russia launched its full-scale invasion, originally planning to film a documentary about Zelenskyy. That project later became the film Superpower, which ended up documenting the war as it unfolded.

During one of their earlier meetings in 2022, Penn even handed Zelenskyy one of his Oscars as a symbolic gesture, saying it should stay in Ukraine until the country wins. In return, Zelenskyy awarded him the Order of Merit III degree. Over the years, Penn has continued to speak publicly about Ukraine’s struggle and has praised Zelenskyy’s leadership, even calling him someone “born for this moment," as reported by The Guardian.

While Penn’s choice to skip the Oscars even after winning for One Battle After Another highlights his long-standing commitment, it also echoes the principled stands that defined his Oscar-winning performances.

Sean Penn’s Oscar wins reflect his bold, principled choices

Sean Penn claimed his first Best Actor Oscar in 2004 for Mystic River, directed by Clint Eastwood, embodying a father's vengeful anguish. Critics hailed his volatile intensity, snarling through Boston streets and courtroom breakdowns, as career-defining, edging out Johnny Depp and Ben Kingsley in a field stacked with heavyweights.

He doubled down in 2009, snatching Best Actor again for Milk, channeling Harvey Milk's charisma and defiance in Gus Van Sant's biopic. Penn's transformation with lisp, mannerisms, and fiery speeches earned raves for humanizing a polarizing figure, beating past winners like Mickey Rourke and Frank Langella.

This anti-glamour ethos directly fuels Penn's 2026 Oscars ditch for Volodymyr Zelenskyy, trading red carpets for Kyiv bunkers, channeling actor-activist fire to spotlight Ukraine's fight when spotlights fade.

What do you think about Sean Penn skipping the Oscars to meet Zelenskyy? Let us know in the comments.

Written by

Pratham Gurung

Edited by

Hriddhi Maitra