Macaulay Culkin had only one reason to watch the 2025 Academy Awards: to see his younger brother, Kieran Culkin, win Best Supporting Actor. Attending the Vanity Fair after-party with his fiancée, Brenda Song, he revealed that he only tuned in for that single moment—certain of the outcome.
“That’s the only thing I watched. True story, true story… I cried,” Macaulay said, recalling his reaction as Kieran’s name was announced. The recognition, earned for his performance in Jesse Eisenberg’s A Real Pain, marked the peak of an award season where he had already received the Golden Globe, SAG Award, BAFTA, and Critics’ Choice Award for the same role.
Macaulay, 44, pointed out that Kieran’s seat at the ceremony was a clear indicator of what was to come. “He was front row, aisle, closest to the stairs. There was no way he was not going to win,” he said.
Brenda Song echoed his confidence. “Of course. Let’s be real. We’re allowed to say that,” she added when asked if she expected Kieran’s victory.
Kieran, 41, recognized his family during his acceptance speech. He brought up a conversation with his wife, Jazz Charton, after winning an Emmy for Succession in 2024. At the time, she had promised to have a third child if he won, believing it was unlikely.
“After the show, we’re walking through a parking lot … and she goes, ‘Oh, God, I did say that!’” Kieran said in his speech. “I guess I owe you a third kid.”
But his response had gone further. “I turned to her and I said, ‘Really, I want four.’ She turned to me—this happened just over a year ago—and she said, ‘I will give you four when you win an Oscar.’”
From her seat, Charton nodded, confirming the promise. Kieran used the opportunity to remind her. “No pressure. I love you. I’m really sorry I did this again, and let’s get cracking on those kids.”
The award solidified his status after years of recognition for his work in Succession and a series of praised performances. His role in A Real Pain stood out throughout the season, earning him widespread acclaim from film organizations, including the New York Film Critics Circle and the Toronto Film Critics Association.
Macaulay, who started acting alongside Kieran as children, expressed pride in his brother’s achievement. While the Oscar belonged to Kieran, the celebration was a family affair.
