A Real Pain Kieran Culkin wins Oscar for Best Supporting Actor

Following up on 2023’s Emmy win for Succession, Kieran Culkin won Best Supporting Actor at tonight’s Academy Award.

By Matt Schimkowitz  |  March 2, 2025 | 7:34pm
Photo: Mark Von Holden/The Academy
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A Real Pain Kieran Culkin wins Oscar for Best Supporting Actor

Twitching, mumbling, and brimming with insults, Kieran Culkin convinced another major awards body to show some sympathy for the irrepressible asshole. Not only that, he’s convinced them to reward the asshole with a man made of gold. Kieran Culkin has won the Academy Award for Best Supporting Actor for his role in A Real Pain, playing the titular real pain. 

Despite being mistaken by many for a sequel to the Damon Wayans military school comedy, Major Payne, A Real Pain stars Kieran Culkin as the obnoxious and antagonistic cousin to Jesse Eisenberg. Amid retracing their familial steps in the Polish town their grandmother fled in World War II, Eisenberg learns to love his annoying cousin, whom he describes as someone who “lights up a room and shits on everything inside it.” 

Culkin emerged atop a crowded field, beating out showier performances from Edward Norton, Guy Pearce, and Culkin’s Succession brother Jeremy Strong and a quieter one in Anora’s Yura Borisov. Yet, his victory over Strong solidifies Culkin as “the eldest boy.” Culkin also won Supporting Actor accolades at the BAFTA, Critics Choice, the Golden Globes, and the Screen Actors Guild Awards. 

A Real Pain didn’t net Eisenberg a nomination for acting, but writing such key phrases as that “lights up a room” line earned him a Best Original Screenplay nomination.

 
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