Kieran Culkin is on cloud nine after winning the Oscar for Best Supporting Actor for his performance in A Real Pain.

Did Macaulay Culkin and wife Brenda Song expect Kieran to win for ‘A Real Pain’? “Of course!” said Song. “Come on, let’s be real.”Macaulay Culkin is celebrating his brother Kieran Culkin’s big night at the Oscars.

Macaulay Culkin shared his reaction to his brother Kieran Culkin's Oscar win during the Vanity Fair Oscar Party livestream.

The Culkin brothers are just what the doctor ordered. While Kieran Culkin was winning his first Oscar for his performance in 'A Real Pain,' big brother Macaulay Culkin was watching it teary-eyed at home.

Macaulay Culkin is not at all surprised that younger brother Kieran Culkin won his first Oscar at the 2024 Academy Awards: 'I cried.'

Macaulay Culkin revealed at the Vanity Fair Oscars party (via Entertainment Weekly) that he cried when his younger brother Kieran Culkin won the Oscar for best supporting actor at the 2025 Academy Awards. It turns out that category was the only part of the Oscars telecast that Macaulay Culkin and his partner, fellow actor Brenda Song, watched.

Macaulay Culkin revealed he got emotional watching his little brother Kieran Culkin win Best Supporting Actor at the Oscars. “I cried,” he told Queer Eye fashion expert Tan France, who interviewed him and his partner,

Kieran Culkin reflects on nearly rejecting his role and the whirlwind of winning an Oscar.