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.

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,

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.

After much success this awards season, Kieran is now a favored contender to win the award for Best Actor in a Supporting Role at the 2025 Oscars. Scroll down for everything to kno