Sean Penn joins elite club of triple Oscars after skipping 2026 Academy Awards

Sean Penn received a symbolic honour in Kyiv after missing the 2026 Academy Awards, where he won Best Supporting Actor for One Battle After Another.

On March 15, he couldn’t attend the ceremony in Los Angeles, with last year’s winner Kieran Culkin accepting the award on his behalf as Penn was in Ukraine, where he has remained an active supporter since the start of the war.

On March 17, he was presented with a unique Oscar statuette by the CEO of Ukrainian Railways, Oleksandr Pertsovskyi. The custom-made trophy was crafted from metal taken from a train damaged during Russia’s invasion of Ukraine.

In a video shared online, Pertsovskyi told the actor, “You’re missing Oscars… so we made this one.”  Pertsovskyi then added in the same thread, “Iron Sean definitely deserved Iron Oscar!”

Penn’s decision to skip the ceremony was reportedly deliberate. Reports state he had travelled to Europe in the days leading up to the Oscars and chose to spend time in Ukraine instead of attending the event.

During his visit, Penn also met with Ukrainian President Volodymyr Zelenskyy, who publicly thanked him for his support. In a message shared online, Zelenskyy described the actor as a “true friend of Ukraine” who has stood by the country since the early days of the war.

Penn has been one of Hollywood’s most vocal advocates for Ukraine since Russia launched its full-scale invasion in February 2022. In 2023, he even gifted one of his previous Oscars to Zelenskyy, suggesting it could be melted down if needed for the war effort.

Sean, thanks to you, we know what a true friend of Ukraine is.
You have stood with Ukraine since the first day of the full-scale war.
This is still true today.
And we know that you will continue to stand with our country and our people. pic.twitter.com/wGneO1rqJI

— Volodymyr Zelenskyy / Володимир Зеленський (@ZelenskyyUa) March 16, 2026