Kieran Culkin is all but guaranteed to win Best Supporting Actor at the 2025 Oscars for A Real Pain — and it'll break a streak going back to 2011.

ET looks back at Kieran Culkin through the years, from his early role in brother Macaulay’s breakout film, 'Home Alone,' to becoming an Oscar-nominated actor for his part in 'A Real Pain.' As a kid, Kieran had memorable roles in films like ‘Father of the Bride’ and ‘She’s All That.

Pearce said he has an acceptance speech he has "thought about for the last three months now – haven't used it once!"

The Best Supporting Actor prize went to A Real Pain’s Kieran Culkin, just as it did at the Golden Globes, the National Board of Review Awards, the New York Film Critics Circle Awards, and the Los Angeles Film Critics Association Awards,

Kieran Culkin wins Best Supporting Actor at the 2025 SAG Awards, making him the clear frontrunner for the Oscar race.

Heavy Oscar favorite Kieran Culkin won the Screen Actors Guild Award for Best Supporting Actor on Sunday for his performance as the spirited but tortured Benji Kaplan in Jesse Eisenberg‘s seriocomic buddy pic A Real Pain.

Kieran Culkin Explains His Adrien Brody DIG During SAG Awards Acceptance Speech (Exclusive) Kieran Culkin chats with ET's Nischelle Turner backstage after winning Outstanding Performance by a Male Actor in a Supporting Role for 'A Real Pain' at the 31st Annual Screen Actors Guild Awards,