Macaulay Culkin celebrated his brother Kieran Culkin's win at the 97th Academy Awards for his supporting role in Jesse Eisenberg's A Real Pain. When speaking at the Vanity Fair Oscars party on the red carpet,

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.

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.