Kieran Culkin has officially cemented his place in Hollywood history by winning the Academy Award for Best Supporting Actor at the 97th Oscars for his performance in A Real Pain. Directed by Jesse Eisenberg, the film follows two estranged cousins who embark on a journey through Poland to explore their family’s past. Culkin’s portrayal of a sharp-witted yet emotionally vulnerable character resonated with audiences and critics alike, earning him widespread acclaim throughout the awards season.
A Long-Awaited Triumph
For years, Culkin had been known as a talented actor often overshadowed by his famous older brother, Macaulay Culkin, who became a household name as Kevin McCallister in Home Alone. While Kieran had his share of notable performances—particularly in Igby Goes Down and Scott Pilgrim vs. the World—it was his role as Roman Roy in HBO’s Succession that catapulted him into mainstream recognition.
Kieran Culkin wins best supporting actor for ‘A Real Pain.’ #Oscars pic.twitter.com/AoUzsWlMiI
— Ramin Setoodeh (@RaminSetoodeh) March 3, 2025
His performance as the youngest and most unpredictable member of the Roy family earned him multiple Emmy and Golden Globe nominations, with a Golden Globe win in 2024. However, his Oscar victory marks the pinnacle of his career, proving his versatility beyond television.
Almost Turned Down the Role
In a surprising revelation, Culkin shared that he almost withdrew from A Real Pain just two weeks before filming began. Coming off the exhausting shoot of Succession, he considered taking a break to spend more time with his family.
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However, producer Emma Stone, who also happens to be his ex-girlfriend, convinced him to stay on board. This decision proved to be a game-changer, as Culkin delivered what many critics called his most nuanced and heartfelt performance to date.
A Playful Yet Emotional Acceptance Speech
During his Oscar acceptance speech, Culkin brought both humor and heartfelt gratitude to the stage. He jokingly referenced a promise he and his wife, Jazz Charton, made about expanding their family:
“Babe, I guess we’re having another kid!”
The audience erupted in laughter and applause as Culkin acknowledged his wife and their children. He then turned emotional, thanking Jesse Eisenberg for his direction and Emma Stone for believing in him. He also gave a nod to his brother Macaulay, saying:
“Mack, we’ve come a long way, huh? Love you, man.”
It was a touching moment that highlighted both his personal and professional journey.
A Clean Sweep Across the Awards Circuit
Culkin’s Oscar win was the culmination of an incredible awards season. Prior to the Academy Awards, he had already taken home the Golden Globe, SAG Award, and Critics’ Choice Award for his role in A Real Pain. This dominance made him the clear frontrunner in the Best Supporting Actor category, and his victory was met with overwhelming support from fans and industry peers.
What’s Next for Kieran Culkin?
With an Oscar now under his belt, Culkin’s career trajectory is bound to reach new heights. While he has not announced his next project, there is already speculation that top directors and studios are eager to work with him. His ability to balance dark humor, emotional depth, and complex character dynamics makes him one of Hollywood’s most exciting talents today.
Additionally, there is curiosity about whether he will venture into directing or producing, following in the footsteps of many actors who have used their Oscar wins as a stepping stone for broader creative endeavors.
A Win Years in the Making
Kieran Culkin’s Oscar moment was more than just an individual achievement—it was a testament to perseverance, talent, and staying true to one’s craft. His journey from a child actor in his brother’s shadow to a critically acclaimed performer has been anything but conventional. Yet, with his unforgettable performance in A Real Pain, he has proven that he is a force to be reckoned with in Hollywood.
