All articles tagged with #sean penn
Sean Penn skipped the Academy Awards to meet Ukrainian President Zelensky in Kyiv; Ukraine’s state rail company Ukrzaliznytsia gifted him a custom Oscar made from metal of a damaged railcar, a symbol of resilience, after Penn had previously donated one of his statuettes to Ukraine.
Sean Penn skipped the 2026 Oscars to be in Ukraine, where he was announced the Best Supporting Actor winner for his role in One Battle After Another. In a symbolic twist, Ukrainian Railways presented him with an 'IronOscar' forged from train-car steel damaged by a Russian missile, as a token of gratitude; Zelensky praised Penn for standing with Ukraine, and Penn expressed gratitude for the gesture. Penn had also won BAFTA and other acting honors that year, while choosing not to attend those ceremonies as well.
Sean Penn skipped the Los Angeles Oscars to visit Kyiv, where President Zelenskyy presented him with a silver Oscar crafted from a damaged Ukrainian rail carriage by the Ukrainian Railways chief; Penn, who won Best Supporting Actor for One Battle After Another, has long supported Ukraine, including lending an Oscar to Zelenskyy in 2022 and making a documentary about the president.
Sean Penn won his third acting Oscar at the 2026 ceremony for One Battle After Another, but was elsewhere: Ukraine, where he met President Zelensky, who publicly thanked him for his support; Zelensky posted a photo of the meeting, resolving the Oscar-night whereabouts mystery.
Sean Penn, who won Best Supporting Actor for One Battle After Another, was in Kyiv on November 8, 2022, spending time with Ukraine’s President Volodymyr Zelenskyy instead of attending the Oscars. Zelenskyy later posted on X thanking Penn as a true friend of Ukraine, noting his support since the 2022 invasion. Penn has spent considerable time in Ukraine, including directing the 2023 documentary Superpower about Zelenskyy’s leadership.
American actor Sean Penn skipped the March 15 Oscars ceremony to travel to Ukraine, where he met President Volodymyr Zelensky in Kyiv. Zelensky praised Penn as a true friend of Ukraine, highlighting his long-standing support and humanitarian work. Penn has visited Ukraine multiple times since Russia’s 2022 invasion, including work on the documentary Superpower and a humanitarian CORE effort; at the LA ceremony he was announced as the Best Supporting Actor winner but sent a representative to accept on his behalf.
Oscar-winning actor Sean Penn skipped Sunday's ceremony and flew to Kyiv on Monday to show support for Ukraine, where he met President Volodymyr Zelensky after winning Best Supporting Actor for One Battle After Another. Zelensky praised him as a true friend of Ukraine, and Penn has previously co-directed a Zelensky-focused documentary and was reportedly planning to visit the eastern front.
Sean Penn won Best Supporting Actor for One Battle After Another at the Oscars but skipped the ceremony to meet President Volodymyr Zelenskyy in Ukraine, with Zelenskyy praising him as a true friend of Ukraine in a public post.
Sean Penn won Best Supporting Actor at the 2026 Oscars for One Battle After Another but did not attend, reportedly traveling to Europe en route to Ukraine. Other no-shows included Brad Pitt and Hailee Steinfeld. Paul Thomas Anderson’s One Battle After Another dominated the night with Best Picture, Best Director, and Best Screenplay, a ceremony during which Penn’s award was accepted on his behalf by Kieran Culkin. Penn’s history of criticising the Academy provides context for his absence.
Sean Penn won his third Oscar, becoming the fourth male actor to reach three competitive wins, taking Best Supporting Actor for One Battle After Another. He did not attend the ceremony, with presenter Kieran Culkin accepting on his behalf. The piece notes Penn’s history of activism and his 2022 Ukraine work, alongside his prior Oscar wins for Milk and Mystic River and his ambivalent relationship with the Academy.
Conan OBrien delivered a rapid-fire Oscars monologue at the Dolby Theatre that mixed brisk jokes about Timothée Chalamet, Sean Penn, and Ted Sarandos with broader political and social jabs, including commentary on healthcare and Epstein-file controversy, and concluded with a sincere note about global uncertainty and optimism amid ongoing turmoil.
Sean Penn won the Best Supporting Actor Oscar for One Battle After Another at the 2026 Oscars, his third acting Oscar, tying the all-time male acting-wins record with Jack Nicholson, Walter Brennan and Daniel Day-Lewis; he did not attend the ceremony, with the win following precursor awards from BAFTA and SAG-AFTRA.
The Hollywood Reporter confirms that the Oscar Sean Penn lent to Ukrainian President Volodymyr Zelensky in 2022 was the Best Actor statuette for Mystic River (not Milk), after re-examining photos to identify which statue was handed over. Penn previously hinted it was a loan rather than a gift and had even threatened to melt the statues if Zelensky didn’t get a chance to speak at the ceremony.
Ahead of the 2026 Oscars, the buzz centers on whether Sean Penn will attend after skipping other awards, whether the return of the 'Fab Five' presenting format is on the table, who will present Best Picture, and potential cast reunions or a flashy opening. Gold Derby predicts which films might dominate and whether international entries break through, all shaping a night of high-stakes suspense.
Sean Penn, 65, was spotted holding hands and shopping in Santa Monica with girlfriend Valeria Nicov on a rare public outing. The couple, linked since 2024 after a Marrakech Film Festival red-carpet debut, have kept their relationship low-key, with their last public sighting in Paris in July 2025. Penn’s outing follows a viral moment at the 2026 Golden Globes.