The Culkin family may be Hollywood royalty at this point, and on Hollywood’s biggest night,Macaulay Culkinmade it clear he was watching only one thing—the momentKieran Culkintook home his first Oscar. At the 2025 Academy Awards,Kieran wonBest Supporting Actorfor his role inA Real Pain, Jesse Eisenberg’sdramedy about two semi-estranged cousins reconnecting in Poland while grappling with intergenerational trauma.
It was the culmination of an impressive awards season run for Kieran, who had already secureda Golden Globe, BAFTA, Independent Spirit Award, and SAG Awardfor the role, anddelivered aSuccessionof tremendously off-the-cuff speechesfrom various podiums around the world.
While attending Vanity Fair’s annual Oscars afterparty,Macaulay, alongside fiancéeBrenda Song, spoke to hostTan Franceabout his brother’s win. And in true older brother fashion, he admitted he only tuned in for one category. “Just theBest Supporting Actor,” Macaulay said. “That’s the only thing I watched. True story, true story.”
Song backed him up, adding that theyknewKieran would win.“Of course. Let’s be real. We’re allowed to say that,” she said.Macaulay agreed, joking that his younger brother’s front-row, aisle seat placement meant there was no doubt:
“There was no way he was not going to win.”
And when the moment arrived, Macaulay revealed his reaction was deeply emotional. “I cried,” he admitted. “And I was like, ‘I’m gonna see you later.’”
A Long Line of Speeches from Kieran Culkin
Onstage, Kieran continued his run of charming acceptance speeches,making sure to thankJesse Eisenbergand his wife,Jazz Charton—while also reminding the latter of a past wager in a car park, which had the audience doubled over with laughter.
Kieran revealed he had won a bet with his wife where she had not only promised they would have a third child if he won an Emmy, but actually said they could have four if he somehow won an Oscar. Well…
“About a year ago, I was on a stage like this, and I very stupidly, publicly, said that I want a third kid from her because she said if I won the award, she would give me the kid.I turned to her and I said, ‘Really? I want four.’ She said, ‘I will give you four when you win an Oscar.’”
The 97th Academy Awards are now available to stream on Hulu.
