Sean Penn skipped Hollywood’s biggest night and still walked away with a trophy … just not the one you’d expect.
The 65-year-old actor bailed on Sunday night’s Academy Awards, where he won best supporting actor for “One Battle After Another,” choosing instead to fly to war-torn Ukraine.
While A-listers gathered at the Dolby Theatre in Los Angeles, Penn was meeting Ukrainian President Volodymyr Zelensky in Kyiv Monday — doubling down on his long-running support for the country amid its ongoing war with Russia.
But Ukraine wasn’t about to let the Oscar winner head back to the US empty-handed.
In a striking moment caught on video posted to X, Ukrainian Railways CEO Oleksandr Pertsovskyi presented Penn with a one-of-a-kind “IronOscar” — a handmade statuette forged from metal taken from a railcar destroyed by a Russian missile.
“You’re missing the Oscars,” Pertsovskyi told him. “Plus, you gave the last one to the president. So we made this one.
“You said the metals survived, so we put some words here that are very special to us. It’s not golden, but it’s very real, and it’s from the bottom of our hearts. It’s important to us.”
An emotional Penn embraced Pertsovskyi, replying simply: “These are all treasures, thank you.”
Sean Penn opted for the trip to
vs. Oscar ceremony at Dolby Theater where he was awarded his 3rd
. We couldn’t leave our great friend and loyal Ukrainian Raiwlays passenger without an award. So, I have presented Sean with our IronOscar on behalf of all of us! pic.twitter.com/OLyzOY4h7L
— Oleksandr Pertsovskyi (@Pertsovskyi_O) March 17, 2026
The makeshift award comes with a powerful inscription etched into its back:
“This steel once carried millions of people away from war. Then a Russian missile came. We did not melt it into a weapon. We forged it into gratitude — for you. For your talent. For your courage to stand with Ukraine.”
Penn’s absence didn’t go unnoticed back in Hollywood.
Actor Kieran Culkin, who announced the category, took a playful jab: “Sean Penn couldn’t be here this evening, or didn’t want to, so I’ll be accepting the award on his behalf.”
Sources told the New York Times that Penn had planned the Ukraine trip days in advance, opting for the visit over attending the ceremony despite going on to clinch his third Oscar.
Penn’s connection to Ukraine runs deep.
He’s visited multiple times since Russia’s 2022 invasion, even filming a documentary about Zelensky’s transformation from comedian to wartime leader. The film premiered in 2023 and helped cement what both men describe as a close friendship.
In 2022, Penn handed one of his own Oscar statuettes to Zelensky — telling him to return it only after Ukraine wins the war.
The actor’s latest Oscar puts him in rare company among acting heavyweights with three Academy Awards, joining Daniel Day-Lewis, Jack Nicholson, Meryl Streep and Ingrid Bergman.
Penn previously won best actor for starring turns in “Mystic River” in 2004 and “Milk” in 2009.
Still, his Oscars absence wasn’t a total shock, as he also missed the Actor Awards in Los Angeles earlier this month and the BAFTAs in London in February.
This time, Penn’s no-show was another reminder that when it comes to awards season, he plays by his own rules.
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