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 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.