When Sean Penn won his third Oscar at the 2026 ceremony, he didn’t show up to collect the award – and Kieran Culkin made a dig at his expense.
Penn won the Best Supporting Actor trophy for his role in Paul Thomas Anderson’s One Battle After Another, having previously won Best Actor for Mystic River and Milk in 2004 and 2009, respectively.
However, after last year’s winner, A Real Pain star Culkin, announced six-time nominee Penn’s victory, he revealed that the actor wasn’t there to claim the award.
According to The New York Times, Penn was visiting Ukraine instead. The actor has been one of the most high-profile supporters of Ukraine’s President Zelensky during his country’s war with Russia.
In his usual wry tone, Culkin poked fun at Penn’s absence, telling the crowd: “Sean Penn couldn’t be here this evening. Or didn’t want to. So I’ll be accepting the award on his behalf.”
Viewers laughed along at Culkin’s comment at home, with one writing on X/Twitter: “Funniest thing said tonight. Kieran Culkin saying it like it is.”
“Oh Kieran you are iconic for this!” another added.
Host Conan O’Brien then joked about the situation, sarcastically stating: “We had a no-show in Sean Penn – this thing’s a humdinger; you’ve got to stay tuned!”
Penn’s victory arrives despite expressing disdain for the ceremony in the past. In 2024, he accused the Oscars of “limiting different cultural expressions” and said that ceremonies like the Oscars should be viewed as “television shows first”.
While receiving a career tribute at Marrakech Film Festival, he said: “The Academy have exercised really extraordinary cowardice when it comes to being part of the bigger world of expression, and in fact, have largely been part of limiting the imagination and very limiting of different cultural expressions.”
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He beat his One Battle After Another co-star Benicio Fel Toro, Delroy Lindo (Sinners), Stellan Skarsgård (Sentimental Value) and Jacob Elordi (Frankenstein), who were all present at the ceremony.
Penn also didn’t show up at several awards ceremonies in the run-up to the Oscars, including the Baftas, where he also won Best Supporting Actor. His win makes him the fourth male actor in history to receive three acting Oscars in total, joining Walter Brennan, Jack Nicholson and Daniel Day-Lewis.
