It was one of the most talked-about moments of the 98th edition of the Academy Awards when veteran actor Sean Penn was announced as the winner of Best Supporting Actor for his performance in One Battle After Another—but was notably absent to accept the honour in person. As presenter Kieran Culkin stepped in to receive the award on his behalf with humour and grace, the audience and viewers around the world were left wondering about Penn’s absence from Hollywood’s biggest night.
The mystery was resolved just hours later when a video surfaced online showing Sean Penn stepping off a train in Kyiv, far removed from the glamour of the Dolby Theatre, where the Oscars ceremony took place. The footage, shared by Ukraine’s state railway operator, revealed that the actor had chosen to travel to the war-affected country instead of attending the awards ceremony.
According to officials, the trip had been kept confidential until his arrival for security reasons. In a statement accompanying the video, the railway operator highlighted Penn’s decision, noting that he had “chosen Ukraine over the Oscars,” a gesture that quickly drew global attention and admiration.
Later that day, Ukrainian President Volodymyr Zelenskyy shared a photograph of his meeting with Sean Penn at the presidential office in Kyiv. The image showed the two engaged in conversation, reflecting a continuation of Penn’s ongoing support for Ukraine amid its ongoing conflict with Russia. While specific details of their discussion were not disclosed, Zelenskyy expressed gratitude for Penn’s consistent advocacy.
“Sean, thanks to you, we know what a true friend of Ukraine is,” Zelenskyy wrote in a message shared on Telegram. He added that Penn had stood with Ukraine since the beginning of the full-scale war and continues to do so, reinforcing the actor’s reputation as a committed supporter of the country during its most challenging times.
Kyiv remains heavily fortified due to the ongoing conflict with Russia under President Vladimir Putin. Despite the risks, Sean Penn has made multiple visits to Ukraine over the past few years, demonstrating his continued solidarity. His involvement goes beyond symbolic gestures—he has actively worked to raise awareness about the war through filmmaking and public advocacy.
In 2023, Penn released a documentary on Russia’s invasion of Ukraine, further amplifying global attention on the crisis. His relationship with Zelenskyy, who himself transitioned from a career in entertainment to politics, has also been widely noted. In 2022, Penn even lent one of his own Oscar statuettes to Zelenskyy as a symbolic gesture of support, asking him to return it when Ukraine emerged victorious.
Meanwhile, Penn’s latest Oscar win marks a significant milestone in his illustrious career. With this victory, he becomes only the fourth male actor to win three Academy Awards for acting. He previously won Best Actor for his roles in Mystic River and Milk, both of which earned critical acclaim and cemented his standing as one of Hollywood’s most respected performers.
His third Oscar places him alongside legendary actors such as Daniel Day-Lewis, Jack Nicholson, and Walter Brennan, all of whom share the record for the most acting wins among male performers. The overall record, however, continues to be held by Katharine Hepburn, who won four Academy Awards during her career.
Sean Penn’s decision to forgo the ceremony in favour of visiting a war zone underscores a rare moment where global politics and cinema intersect. While many actors celebrate their achievements on the Oscars stage, Penn chose instead to use his platform to highlight a cause he deeply believes in—making his absence as impactful as his win.