Kieran Culkin won the Oscar for best supporting actor Sunday at the 97th Academy Awards, completing a sweep of the category that followed his dominance in television awards last season. The award, for portraying the chaotic but endearing Benji in Jesse Eisenberg’s “A Real Pain,

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.