Kieran Culkin is taking home his first Oscar for his performance in the Jesse Eisenberg film “ A Real Pain .” Culkin, who was a favorite to win best supporting actor heading into the 97th Academy Awards Sunday, has consistently won accolades for the role throughout awards season.

Kieran Culkin won Best Supporting Actor at the 2025 Oscars on Sunday for his role in Jesse Eisenberg’s movie, “A Real Pain,” a victory that wouldn’t have been achieved if the star had his way.

As Jesse Eisenberg’s “A Real Pain” heads into Oscars weekend with two nominations following a fruitful awards season as a critical darling, it’s hard to believe the film was once turned down by every single distribution company approached (bet they’re kicking themselves now).