Macaulay Culkin reveals emotional reaction to brother Kieran’s Oscar win

Kieran won best supporting actor for his role in Jesse Eisenberg’s ‘A Real Pain’

Macaulay Culkin revealed that watching brother Kieran’s first Oscar win made him quite emotional.

Speaking to host Tan France on the red carpet of the annual Vanity Fair Oscars afterparty in Los Angeles, the actor said that he only watched one category and cried when the Succession actor won.

Asked if he had watched the entire show, Macaulay replied: “Just the best supporting actor. That’s the only thing I watched. True story, true story.”

France asked if Macaulay had reached out to Kieran after the win. “I cried,” he replied. “And I was like, ‘I’m gonna see you later.’”

Asked if they expected Kieran to win, Macaulay’s partner Brenda Song said: “Of course. Let’s be real. We’re allowed to say that.”

“Yeah, absolutely,” Macaulay replied. “He was front row, aisle, closest to the stairs. There was no way he was not going to win.”

Macaulay Culkin revealed he cried watching brother Kieran’s first Oscar win (AFP via Getty)

Macaulay Culkin, left, and Kieran Culkin in New York City in February 2005 (Getty)

Kieran, 42, won the award for his role as Benki Kaplan in A Real Pain, opposite Jesse Eisenberg. They play two cousins on a Jewish heritage tour in honour of their late grandmother.

Kieran was the favourite to win after sweeping the awards season with best supporting actor wins at the Golden Globes, Critics’ Choice, BAFTAs, and SAG. He had been nominated alongside Guy Pearce for The Brutalist, Yuriy Borisov for Anora, Edward Norton for A Complete Unknown, and Succession co-star Jeremy Strong for playing Roy Cohn in the Donald Trump biopic The Apprentice.

Taking his award from Robert Downey Jr, Kieran started by praising Strong. “Jeremy, you're amazing in The Apprentice,” he said. “I love your work, it's f***ing...I'm not supposed to single anyone out, it’s favouritism, but you were great.”

He went on to thank his manager, his mother, Eisenberg, and his wife Jazz Charton, reminding her of a deal the couple had made.

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“About a year ago, I was on the 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," he said, recalling his speech from the Emmys last January.

After the show, “She goes, oh, God, I did say that. I guess I owe you a third kid. And I turned to her and I said, really? I want four.”

“She said, I will give you four when you win an Oscar,” said Kieran. “Jazz, love of my life. Ye of little faith. No pressure, I love you.”

Kieran Culkin was a favourite to win after sweeping the awards season with best supporting actor wins at the Golden Globes, Critics’ Choice Awards, SAG Awards, and BAFTAs (AFP via Getty)

A Real Pain, which premiered at the 2024 Sundance Film Festival, opened to generally good reviews, with The Independent critic Clarisse Loughrey writing in her four-star review: “A Real Pain is – and has been designed to be – Culkin’s film, and the exposed nerve quality of his performance has already seen him richly rewarded, most recently with a Golden Globe. Benji works so well as a character because the actor offers equal attention to his skittish, surface qualities and the deeper turmoil that drives them. He’s funny and unpredictable at first, even a little antisocial, but it hurts when all the pieces finally click tragically into place.”

Find the full list of the 2025 Oscar winners here.

This year’s Oscars competition was the closest in years, a three-horse race between Sean Baker’s critic’s darling Anora, Brady Corbet’s sweeping epic The Brutalist and Pope drama Conclave.

In the event, Anora became the evening’s big winner, taking home five trophies, including best picture.