Macaulay Culkin ‘Cried’ Over Brother Kieran’s Oscar Win and Only Watched His Category: ‘There Was No Way He Was Not Going to Win’

Macaulay Culkin shared an emotional moment at the Vanity Fair Oscars party, revealing that he cried when his younger brother, Kieran Culkin, won the Oscar for Best Supporting Actor at the 2025 Academy Awards. The heartfelt admission came during an interview with Entertainment Weekly, where Macaulay explained that the Oscars telecast was something he and his partner, actress Brenda Song, didn’t watch in its entirety. Instead, the only part of the ceremony they tuned in for was the Best Supporting Actor category.

“Just the Best Supporting Actor,” Macaulay Culkin said when asked about watching the show. “That’s the only thing I watched. True story, true story… I cried. And I was like, ‘I’m gonna see you later.’” The emotional moment showcased not only his pride for his brother’s achievement but also the close bond they share.

Kieran Culkin’s win was a major highlight of the 2025 Oscars. He took home the coveted statue for his performance in A Real Pain, a film directed by Jesse Eisenberg. Culkin’s portrayal in the movie garnered widespread acclaim, earning him the title of the frontrunner for the Best Supporting Actor category. His competition included notable nominees such as Yura Borisov for Anora, Edward Norton for A Complete Unknown, and Guy Pearce for The Brutalist.

Kieran’s win at the Academy Awards marked the culmination of a remarkable awards season, where he had already racked up numerous accolades, including wins at the Golden Globes, Critics’ Choice Awards, SAG Awards, and BAFTAs. His recognition at the Oscars solidified his status as one of Hollywood’s most talented and promising actors.

Macaulay Culkin’s heartfelt reaction to his brother’s victory only underscored the deep familial bond between the two actors, as they both continue to make their mark in the entertainment industry.

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