Kieran Culkin's unexpected win at the 2025 Academy Awards for Best Actor in a Supporting Role has taken him by surprise, especially considering his initial skepticism about A Real Pain's success. Culkin recalled his manager's words suggesting the film might only reach a limited audience. This win follows a clean sweep at major awards, including the Golden Globes and BAFTAs. During his acceptance speech, Culkin expressed gratitude to his co-star Jesse Eisenberg and playfully referenced a promise made regarding having more children if he won an Oscar.
I thought it was going to be this thing that Jesse [Eisenberg] and I thought was cool, and at best it’s a movie that goes to Sundance.
Culkin's first Oscar marked the culmination of his sweep this year, adding to his collection of awards from the 2025 Golden Globes, the Critics Choice Awards, the BAFTAs, and the Screen Actors Guild Awards.
I have no idea how I got here, Culkin said in his acceptance speech on Sunday night. I've just been acting my whole life.
Culkin turned toward his wife, Jazz Charton, to remind her that she once told him they could have more children if he ever won an Oscar.
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