The Brief

Sean Penn won Best Supporting Actor at the 98th Academy Awards for his role in One Battle After Another, tying the all-time male record with three acting Oscars. He was not at the Dolby Theatre. An AFP reporter spotted him in central Kyiv on Monday morning, and a senior Ukrainian official confirmed he is expected to meet President Zelensky.

The Report

Sean Penn won his third Academy Award on Sunday night, taking Best Supporting Actor for his portrayal of the bigoted Col. Steven J. Lockjaw in Paul Thomas Anderson’s One Battle After Another. He was not present to collect it. Presenter Kieran Culkin accepted the statuette on his behalf, telling the audience Penn “couldn’t be here this evening — or didn’t want to.”

Hours later, an AFP reporter observed Penn stepping out of a black car in central Kyiv, wearing sunglasses and carrying a box of cigarettes. A senior Ukrainian official confirmed his presence to AFP, describing the trip as personal. “He just wants to support Ukraine,” the official said. A second source indicated Penn is planning to visit the front lines in eastern Ukraine. He is expected to meet with President Volodymyr Zelensky later on Monday.

The win places Penn alongside Walter Brennan, Jack Nicholson, and Daniel Day-Lewis as the only men to win three acting Oscars. It is his first in a supporting category, following Best Actor wins for Mystic River in 2004 and Milk in 2009. He beat a field that included co-star Benicio Del Toro, Delroy Lindo, Jacob Elordi, and Stellan Skarsgård.

Penn’s absence surprised no one who has followed his career. He skipped ceremonies for all three of his prior nominations that did not result in wins — Dead Man Walking in 1996, Sweet and Lowdown in 2000, and I Am Sam in 2002. This awards season, he was also absent from the BAFTAs and the Actor Awards, where he won in the same category. “The award world is for me… hell,” he told Newsweek in a recent interview. “I’d rather not be nominated than be pressured to have to participate.”

His relationship with Ukraine predates any awards controversy. Penn was in Kyiv on February 24, 2022 — the first day of Russia’s full-scale invasion — filming what became the documentary Superpower, which profiled Zelensky’s transformation from comedian to wartime leader. He made seven trips to Ukraine over two years of production. In November 2022, he pulled his Mystic River Oscar from a duffel bag and handed it to Zelensky, calling it a loan: “When you win, bring it back to Malibu.” In 2025, he appeared on the Cannes red carpet alongside Bono and Ukrainian soldiers, calling Western hesitancy on Ukraine a “deviant, cowardly” betrayal.

One Battle After Another dominated the 98th ceremony, winning six of its thirteen nominations, including Best Picture and Best Director for Anderson — who had previously lost eleven consecutive Oscar nominations. Anderson’s acceptance speech for Best Picture ran four words: “Let’s have a martini.”

Penn’s representatives have not commented on his travel plans. Whether the Kyiv trip was timed to replace the ceremony or simply happened to coincide with it remains unclear — though his record suggests the ceremony was never the priority.

The Angle

The interesting thing about Penn’s absence is what it makes visible by contrast. An industry built on self-celebration handed its highest individual honour to a man who had already decided to be somewhere else — and the somewhere else was not a beach. It was a country entering its fifth year of war, with postponed peace negotiations and dwindling air defence stockpiles. Culkin’s quip landed well in the room. Outside it, the arithmetic is less comfortable: one man chose a war zone over an awards show, and the awards show carried on without noticing the implied judgement. The Academy does not require attendance. It has never had to reckon with what a conspicuous absence says about what it is asking people to attend.