Sean Penn Wins Best Supporting Actor Oscar for ‘One Battle After Another’ While in Ukraine

Sean Penn secured the Oscar for Best Supporting Actor on Sunday night for his portrayal of Colonel Steven J. Lockjaw in Paul Thomas Anderson’s critically acclaimed film, One Battle After Another. However, the actor was not present at the ceremony, opting instead to continue a visit to Ukraine, a country he has publicly supported.

A Third Oscar for Penn

This win marks Penn’s third Academy Award, and his first in the supporting actor category. He previously received Best Actor Oscars for Mystic River (2003) and Milk (2008). He had been nominated three prior times for leading roles before this year’s win. Penn joins a select group of actors – including Meryl Streep, Jack Nicholson, Ingrid Bergman, Daniel Day-Lewis, Frances McDormand, and Walter Brennan – who have earned three acting Oscars.

Competition and Recognition

Penn triumphed over a strong field of nominees, including his co-star Benicio del Toro for his performance in One Battle After Another, Jacob Elordi for Frankenstein, Delroy Lindo for Sinners, and Stellan Skarsgård for Sentimental Value. Prior to the Oscars, Penn had already received recognition for the role, winning Best Supporting Actor at the British Academy Film Awards (BAFTAs) and the Actor Awards.

One Battle After Another: A Critical and Commercial Success

One Battle After Another, released in September 2025, is a black comedy action-thriller directed and written by Paul Thomas Anderson. The film, inspired by Thomas Pynchon’s novel Vineland, features an ensemble cast including Leonardo DiCaprio, Sean Penn, Benicio del Toro, Regina Hall, Teyana Taylor, and Chase Infiniti. The film follows an ex-revolutionary forced back into a combative lifestyle while being pursued by a corrupt military officer. With a budget of $130–175 million, it grossed over $209.7 million worldwide.

Penn’s Continued Support for Ukraine

According to reports, Penn left for Europe prior to the Oscars to visit Ukraine, continuing his longstanding support for Ukrainian President Volodymyr Zelensky. He previously gifted Zelensky one of his Oscar statuettes in 2022.