Actor Sean Penn earned his third Academy Award at the 2026 Oscars for Best Supporting Actor in Paul Thomas Anderson’s One Battle After Another, joining a select group of performers with that distinction. The 65-year-old star skipped the ceremony at Los Angeles’ Dolby Theatre on Sunday night.
Succession actor Kieran Culkin, last year’s Best Supporting Actor winner, accepted the award and quipped, “Sean Penn couldn’t be here this evening, or didn’t want to, so I’ll be accepting the award on his behalf.”
Sources confirm Penn chose to travel to Ukraine instead. Reporters spotted him arriving by car in Kyiv on Monday, followed by photos of his meeting with President Volodymyr Zelensky. This decision to prioritize a war-torn nation over Hollywood glamour aligns with Penn’s recent activism focused on Ukraine.
Penn’s Longstanding Activism
Penn’s commitment stems from a family legacy of liberal politics. His father, actor and director Leo Penn, faced Hollywood blacklisting in the 1950s for refusing to testify before the House Un-American Activities Committee.
Penn emerged as a vocal critic during the early 2000s Iraq War under President George W. Bush. Skeptical of claims about weapons of mass destruction, he published a full-page ad in The Washington Post in 2002 urging Bush to reconsider. He later visited Baghdad to document the human impact, stating he aimed to make “their blood – along with that of American soldiers – … not … invisible on my own hands.”
His hands-on efforts continued with rescue operations after Hurricane Katrina in New Orleans and founding a major refugee camp in Haiti post-2010 earthquake. Aid workers praised the camp’s effectiveness, leading to Penn’s appointment as Haiti’s ambassador-at-large.
Not all initiatives drew universal acclaim. Critics questioned his support for leaders like Venezuela’s Hugo Chávez and Cuba’s Raúl Castro. His 2015 interview with drug lord El Chapo for Rolling Stone sparked controversy, with Penn later expressing regret over the distractions from drug war discussions.
From Documentary to Deep Alliance
Penn’s Ukraine involvement began as a potential lighthearted documentary on Zelensky, a former actor and comedian who rose to presidency via an anti-corruption platform mirroring his TV role. Filming delays from the COVID-19 pandemic pushed production to late 2021.
Penn met Zelensky on February 23, 2022, the day before Russia’s invasion. Their filmed session the next day captured the war’s outset. Penn noted a profound change in Zelensky, saying, “I saw a very big change in him from one day to the next. … At that moment, he was the significant target. But he wasn’t going anywhere. That day, he found out that he was born for this.”
Zelensky’s decision to remain in Kyiv impressed Penn, who declared, “President Zelensky and the Ukrainian people have risen as historic symbols of courage and principle. Ukraine is the tip of the spear for the democratic embrace of dreams. If we allow it to fight alone, our soul as America is lost.”
The resulting documentary, Superpower, premiered at the 2023 Berlin Film Festival. Penn embraced its pro-Ukraine stance, stating, “If it’s propaganda, I’m proud.”
Ongoing Support Amid Global Tensions
Penn lent one of his Oscars to Zelensky in late 2022, saying to return it to Malibu only after Ukraine’s victory: “It’s just a symbolic silly thing, but if I know this is here with you then I’ll feel better and stronger for the fight.” Zelensky reciprocated with Ukraine’s Order of Merit.
In 2025, after a strained White House meeting between Donald Trump and Zelensky, Penn praised the Ukrainian leader as “constantly, extemporaneously genuine” in pursuing freedom. He added, “I think the last significant moment that we [Americans] were bridging a division was in support of Ukraine and its head of state. And if we lose track of that, we really have to ask ourselves if we’re losing track of the value of democracy.”
Penn visited Ukrainian special forces weeks later and appeared at the 2025 Cannes Film Festival with soldiers, U2’s Bono, and The Edge. A senior Ukrainian official described his latest Kyiv trip as a personal show of support: “It’s his personal visit, that’s how he sees it, that he needs to be in Ukraine. He just wants to support Ukraine.”
Penn’s third Oscar underscores his unwavering, action-oriented advocacy for Zelensky and Ukraine.
