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

Kieran Culkin tried to quit the role of a lifetime. The actor took home the Academy Award for Best Supporting Actor on Sunday ...

Macaulay Culkin revealed at the Vanity Fair Oscars party (via Entertainment Weekly) that he cried when his younger brother ...

Though Kieran Culkin won Best Supporting Actor for A Real Pain at the 2025 Oscars, he originally tried backing out of the ...

Kieran Culkin won the best supporting actor Oscar on Sunday for playing a motor-mouthed American tourist in "A Real Pain." A ...

Proud sibling Macaulay Culkin is not at all surprised that his younger brother, Kieran Culkin, won his first Oscar at the ...

Selena Gomez and fiancé Benny Blanco made an early exit, and Kieran Culkin continued his quirky jokes. Here's what you didn't ...

After sweeping multiple awards bodies, Kieran Culkin wins Oscar for Supporting Actor for his role in Jesse Eisenberg's 'A ...

Kieran Culkin is taking home his first Oscar for his performance in the Jesse Eisenberg film “ A Real Pain .” Culkin, who was ...

The award, for portraying the chaotic but endearing Benji in Jesse Eisenberg’s “A Real Pain,” marked his first win and ...

The first and most widely predicted result of the night came to pass with Kieran Culkin’s win for his performance in “A Real ...

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.