Macaulay Culkin ‘Cried’ Over Brother Kieran Culkin’s 2025 Oscar Win

Macaulay Culkin had an emotional reaction to brother Kieran Culkin taking home a trophy at the 2025 Oscars.

While at the Vanity Fair Oscar party on Sunday, March 2, Macaulay, 44, and fiancée Brenda Song gushed over Kieran 42, winning Best Actor in a Supporting Role thanks to his performance in A Real Pain. (Anora’s Yura Borisov, A Complete Unknown’s Edward Norton, The Brutalist’s Guy Pearce and The Apprentice’s Jeremy Strong were also nominated in the category.)

“Just the Best Supporting Actor, that’s the only thing I watched. True story, true story,” Macaulay quipped to Tan France when asked if he watched the awards show held at Los Angeles’ Dolby Theatre. As for whether he communicated with Kieran following the win, Macaulay said, “I cried. And I was like, ‘I’m gonna see you later.’”

Macaulay noted that he wasn’t sure whether he was going to cross paths with Kieran at the after party, joking that his brother is a “busy man.” Macaulay quipped, “He’s Academy Award-winning actor Kieran Culkin.”

Song, 36, gushed that the couple was “of course” expecting Kieran to take home the trophy. “Come on, let’s be real. We’re allowed to say that,” Song said, while Macaulay pointed to Kieran’s seating arrangement at the ceremony. “He was front row, aisle, closest to the stairs. There was no way he was not going to win.”

While accepting the award on Sunday, Kieran left out Macaulay from his speech — but gave a sweet shout-out to his wife, Jazz Charton.

“Please don’t play the music, because I want to tell a really quick story about Jazz. A year ago, I said that I want a third kid — because she said if I won the [Emmy] award [for Succession], she would give me the kid. Turns out she said that because she didn’t think I was going to win,” Kieran recalled. “People came up to me and were like, you know, really annoying her, it got to her. But anyway — after the show we’re walking through a parking lot, she’s holding the Emmy, she goes, ‘Oh, god, I did say that. I guess I owe you a third kid.’ I turned to her, I said, ‘Really, I want four.’ And she turned to me, I swear to god this happened, she said, ‘I will give you four when you win an Oscar.’ I held my hand out, she shook it and I have not brought it up once until just now.”

Kieran concluded, “You remember that, honey? Then I just have to say to you, Jazz, love of my life, ye of little faith, no pressure. I love you. I’m really sorry I did this again. And let’s get cracking on those kids, what do you say? I love you.”