Sean Penn Skips 98th Academy Awards to Meet President Zelenskyy in War-Torn Kyiv

Sean Penn skipped the 98th Academy Awards ceremony on March 15, 2026, where he won the Oscar for Best Supporting Actor, to travel to Ukraine for a private visit, meeting Ukrainian President Volodymyr Zelenskyy in Kyiv on March 16, 2026. Penn, 65, took the award for his role in the political thriller "One Battle After Another," directed by Paul Thomas Anderson, according to Reuters. Zelenskyy shared a photograph of the encounter and described Penn as a "true friend of Ukraine." The visit unfolded as Russian drones struck Kyiv, with debris from the attacks falling on Maidan Square, according to ANSA.

Penn traveled through Poland to reach Kyiv Penn reportedly traveled to Ukraine via Poland, according to Polish outlet Super Express. His team kept the plans confidential until the last moment, according to RMF24. The decision to forgo the ceremony in favor of the trip drew wide attention, given that Penn was collecting his third Academy Award — a milestone in any actor's career. Penn's role in "One Battle After Another" was described by Reuters as that of an obsessed military officer in a political thriller. The timing of the visit, coinciding with the Oscar night, underlined Penn's longstanding public engagement with the conflict in Ukraine.

Zelenskyy calls Penn a "true friend" amid drone attacks Ukrainian President Volodymyr Zelenskyy, who has served as the sixth president of Ukraine since 2019, posted a photograph of the meeting with Penn on social media. Zelenskyy described Penn as a "true friend of Ukraine," according to ANSA and Polsat News. The meeting took place against the backdrop of a Russian drone attack on Kyiv, with fragments from intercepted or downed drones landing on Maidan Square, ANSA reported. Penn's visit was characterized as private in nature, according to HotNews.ro. The encounter added a prominent public dimension to Penn's continued personal engagement with Ukraine during the ongoing conflict.

Penn plans to visit front lines after Kyiv meeting Following his meeting with Zelenskyy, Penn expressed a desire to travel to the front lines of the conflict, according to HotNews.ro. No further details on the timing or location of any such visit were confirmed in the available reports. Penn has maintained a visible connection to Ukraine since Russia launched its full-scale invasion in February 2022. In March 2022, Penn was reported by Reuters to have been among thousands of people fleeing to Poland on foot. In November 2022, Penn loaned his Oscar statuette to Zelenskyy as a symbolic gesture of solidarity, according to web search results. Russia placed Penn under sanctions in September 2022 in response to his public criticism of Moscow's military campaign, according to Reuters. Penn's third Oscar win, combined with his decision to travel to a war zone on the night of the ceremony, drew significant media coverage across Europe and North America. His visit to Kyiv came as diplomatic and military activity around the conflict remained intense, though no confirmed information is available on what specific matters Penn and Zelenskyy discussed beyond the characterization of the meeting as private.