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.

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. When speaking at the Vanity Fair Oscars party on the red carpet,

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

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 proud sibling admittedly only tuned in to his brother's category during the live telecast.Proud sibling Macaulay Culkin is not at all surprised that his younger brother, Kieran Culkin, won his first Oscar at the 2025 Academy Awards.

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.

After dominating his category all awards season, Kieran Culkin completed the sweep Sunday, taking home the prize for Best Supporting Actor at this year’s Oscars. After accepting from last year’s winner Robert Downey Jr. Culkin thanked several people including Jesse Eisenberg with the kindest compliment.

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.

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