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How Macaulay Culkin reacted to brother Kieran’s Oscars 2025 win

Brotherly love!

Macaulay Culkin, 44, was proud of his younger brother, Kieran Culkin, 42, after bringing his Oscar home at the 97th Annual Academy Awards on Sunday.

The “Home Alone” star revealed that Kieran “cryed” for the awards that he accepted the statue and praised his competitors Yura Bolisov (“Anora”), Edward Norton (“The Complete Unknown”) and Guy Pierce (“Brutalist”).

Kieran Culkin accepts Best Actor in the Supporting Role Award for “Real Pain” at Oscar 2025. Getty Images
Brenda Song and Macaulay Culkin will be taking part in the 2025 Vanity Fair Oscar Party. Getty Images

Macaulay discussed the brothers' victory at the hottest afterparty of the night – Vanity Fair's Post Oscar Bash – While walking down the red carpet with his wife, actress Brenda Song.

“I just had the best support actor, that's the only thing I've seen. He told correspondent Tan France about watching the star-studded ceremony. “I cried,” he said of his reaction to Kieran's victory. “And I was like, 'See you later.' ”

This was Kieran's first Oscar nomination, winning his role in Jesse Eisenberg's film “A Real Pain.”

This was Kieran Culkin's first Oscar nomination and victory. Ampas/AFP via Getty Images
Kieran Culkin and his wife, Jazz Charton, celebrate his victory. John Rocher/Invision/AP
Kieran Culkin poses with his golden statue. Reuters

In the flick, Kieran plays Benji Kaplan, who travels to Poland with his cousin (Eisenberg) to honor his grandma. However, meaningful vacations include some twists and turns as family tensions resurface.

Macaulay and Son said they had always known that Kieran would leave the winner at the 2025 Oscars. In fact, he swept the awards season, winning Golden Globes, Critics Choice Awards, BAFTA, and Screen Actor Guild Awards for his roles in the film.

When asked if they were confident in his victory, the song replied. Now, let's be real. We are allowed to say that. ”

Brenda Song and Macaulay Culkin. Vanity Fair Wire Image
Macaulay Culkin (L) and Kieran Culkin (R) in 2005. Getty Images

“Yeah, absolutely,” Macaulay added, noting the close placement of Kieran near the awards show stage.

Kieran sat in the “front row aisle, closest to the stage,” his brothers shared. “There was no way he wasn't going to win.”

Macaulay and Song were celebrating Kieran's victory at the Vanity Fair Party, but the Oscar winner was discovered in two separate bashes. He joined his wife Jazz Charton in the Governor Ballroom at the Dolby Theatre, at the Raided Dolby Ballroom, and the pair then headed out to search light an Oscar party at Cipriani Beverly Hills.

In the middle of the night, Kieran was photographed partying with Eisenberg and Emma Stone, the producer of “Real Pain.”

Kieran Calkin from Governors Ball follows the Oscar Show at the 97th Academy Awards in Hollywood. Reuters
Kieran Culkin and Alan Bergman posted an Oscar celebration at Cipriani Beverly Hills. Getty Images for Searchlight Pictures

Macaulay and Songs laughed when asked if they would meet Kieran on a big night.

“I don't know, he's a busy guy!” Macaulay said. “He's Academy Award-winning actor Kieran Culkin.”

Post film critic Johnny Olexinski wrote that the recent Oscar ceremony was a “slow” and “strange” event, but one of the highlights was Kieran's speech.

When accepting Oscars, the “Succession” alumni used the moment to remind his wife of what they had promised if they won an Academy Award.

Oscar winner Kieran Culkin. AFP via Getty Images
Kieran Culkin kisses his wife to celebrate. AFP via Getty Images

“This – I want to talk really briefly about jazz, so don't play music. About a year ago I was on a stage like this and I was very stupid and publicly said I wanted a third child from her.

“She said she didn't think I would win, so she came up to her and said she really seemed to bother her.

Kieran Culkin. FilmMagic

“Emily, you were there so you're a witness and she'll go. I think I owe you a third child,” I turned to her and I said, “I really want four.” And she turned to me and I swear to God that this had happened, and it was exactly a year ago, she said, “When you win the Oscar, I will give you four.” I held out my hand, she rocked it, and I've never raised it before,” Kieran added.

“You remember that, honey? You do it? Then I just say this to you, jazz, the love of my life, you are a little faith. There is no pressure. I love you. Sorry to try again. And let's crack those kids. What do you say? I love you!”

The pair got married in 2013 and share two children. At least for now!

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