“Sean Penn couldn’t be here this evening—or didn’t want to,” said Kieran Culkin during the 2026 Academy Awards, where Sean Penn won Best Supporting Actor for his role in One Battle After Another. This win marks Penn’s third Oscar, adding to his previous accolades for Mystic River in 2004 and Milk in 2009.
Despite the significant achievement, Penn was notably absent from the ceremony, reportedly traveling to Ukraine. His character in One Battle After Another, Colonel Steven J. Lockjaw, has garnered rave reviews, contributing to the film’s overall success, which also won the Best Picture Oscar.
Throughout his career, Penn has been an outspoken figure, often critical of the Academy and its handling of political issues. He has visited Ukraine multiple times since the onset of Russia’s full-scale invasion, highlighting his commitment to the region. During a previous visit, he famously gave one of his Oscars to President Volodymyr Zelenskyy.
“Actor and director Sean Penn is working on a documentary about the war in Ukraine,” Zelenskyy noted, emphasizing Penn’s ongoing involvement in humanitarian efforts. The purpose of Penn’s latest trip remains unclear, with details yet to be confirmed.
In a statement reflecting on the Oscars, Penn remarked, “The Oscars producer thought, ‘Oh, he’s not light-hearted enough.’ Well, guess what you got instead? Will Smith!” This comment underscores his views on the Academy’s choices and the broader implications of political discourse in Hollywood.
Additionally, Penn participated in the anthology film War Through the Eyes of Animals for a symbolic fee of one dollar, further demonstrating his dedication to important causes. His performance in One Battle After Another had been surrounded by Oscar buzz, culminating in this prestigious recognition.
As the night unfolded, Paul Thomas Anderson, who also spoke at the event, said, “To say sorry, for the housekeeping mess that we left in this world we’re handing off to them.” This sentiment resonates with many in the industry as they reflect on their responsibilities.
Sean Penn’s absence at the Oscars, juxtaposed with his significant win, highlights the complexities of celebrity engagement with global issues. His commitment to Ukraine and the arts continues to shape his legacy in Hollywood.
Details remain unconfirmed regarding whether Penn ultimately arrived in Ukraine after his departure from the United States.
