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.

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 and Jesse Eisenberg both stopped separately on the 2025 Oscars red carpet and each chatted with Access Hollywood’s Mario Lopez and Kit Hoover. They were offered shots, and had different ways of drinking them!

The star, who nabbed the best supporting actor Academy Award, received some memorable feedback from his wife about his performance in 'A Real Pain.'

Kieran Culkin thanks Jesse Eisenberg's sister Hallie, the iconic '90s Pepsi girl, in SAG Awards speech for casting him in 'A Real Pain.'

She said, ‘I will give you four when you win an Oscar,’” Culkin, who has two kids with Charton, said to a chorus of laughs from the audience. “Jazz, love of my life, ye of little faith. No pressure. I love you.

Kieran Culkin took home the Oscar for Best Supporting Actor at the 2025 Academy Awards for his role as Benji Kaplan in Jesse Eisenberg's A Real Pain.