The Oscar Went to Sean Penn — But Kieran Culkin Had to Sign for It

If you blinked, you might have thought the Best Supporting Actor announcement had gone wrong at the 98th Academy Awards. Sean Penn was named the winner for One Battle After Another, but when no one appeared from the wings, presenter Kieran Culkin stepped forward with a wry comment about Penn’s preference — or inability — to attend the ceremony. It was a moment that drew confused laughter from the audience before giving way to genuine applause.
Penn’s victory was his third Oscar, cementing his place in the record books alongside Jack Nicholson, Daniel Day-Lewis, and Walter Brennan — each of whom has also won three acting Oscars. Penn previously received the Best Actor prize for Mystic River in 2004 and Milk in 2009. No male actor in Oscar history has ever gone beyond three wins.
One Battle After Another gave Penn the role of an obsessively militaristic officer whose worldview ultimately becomes his undoing. Paul Thomas Anderson directed the film and also walked away with two awards — Best Adapted Screenplay and Best Director — in what many observers described as a long-overdue recognition of his filmmaking genius. The film swept several key categories.
Conan O’Brien was an energetic and thoughtful host, opening with a joke about AI and closing his introduction with an appeal to hope and unity. He noted that the nominees represented 31 countries across six continents — a point that spoke to the increasingly borderless nature of global cinema. His hosting style was both entertaining and, at times, genuinely moving.
Michael B. Jordan was named Best Actor for Sinners, beating Leonardo DiCaprio in a widely anticipated showdown. The 2026 Oscars had no shortage of memorable moments, but Penn’s empty-stage win was perhaps the most singular of all.