Kieran Culkin Wins Best Supporting Actor at the 2025 Oscars
Alright, let’s talk about one of the biggest wins of the 2025 Oscars—Kieran Culkin! If you’ve been following the awards season, this one shouldn’t come as a shocker. Culkin has been sweeping up trophies left and right, from the Golden Globe to the BAFTA and the Screen Actors Guild Award. And now, he’s got the biggest one of them all—the Oscar for Best Supporting Actor for his role in A Real Pain !
Now, if you haven’t seen A Real Pain yet, it’s a comedy-drama directed by Jesse Eisenberg. Culkin plays Benji, the troubled but charismatic cousin of Eisenberg’s character, David. The two embark on a journey through Poland, exploring their Jewish heritage, and along the way, there’s a mix of humor, emotion, and those deep, introspective moments that make a film unforgettable. Critics have been raving about Culkin’s performance, calling it both hilarious and deeply moving. And clearly, the Academy agreed!
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His acceptance speech? Pure Kieran Culkin—relaxed, funny, and full of heart. He gave a shoutout to Robert Downey Jr. for handing him the award and even had a little moment for his Succession co-star Jeremy Strong, calling him “f***ing great” in The Apprentice . And, of course, he didn’t forget to thank Jesse Eisenberg, calling him “a genius,” as well as his longtime agent, his mother, and his stepfather.
But the real kicker? Culkin made a hilarious callback to his Emmy-winning moment last year. At the time, his wife, Jazz Charton, had promised him a third child if he won. After that win, she upped the stakes—if he won an Oscar, they’d go for baby number four! On stage, Culkin made sure to remind everyone that she shook his hand on that deal. “No pressure,” he joked, “but let’s get cracking on those kids.”
Culkin’s journey to this Oscar has been incredible. Most people remember him as the younger brother of Home Alone star Macaulay Culkin, but he’s built an impressive career in his own right. From his breakout role in Igby Goes Down to his award-winning turn as Roman Roy in Succession , he’s proven time and again that he’s got the talent and the range. And now, with an Oscar in hand, he’s officially in Hollywood’s elite.
It’s been a massive night overall at the 2025 Oscars. Anora dominated, taking home Best Picture, with Sean Baker winning multiple awards, including Best Director and Best Original Screenplay. But Kieran Culkin’s win? That’s one of those moments that’ll be talked about for a long time.
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