Kieran Culkin has made headlines by winning his first Academy Award for Best Supporting Actor for his role in "The Real Pain" at the Oscars held on March 2, 2025. This prestigious award was presented to him by Robert Downey Jr., who himself has won the award for his role in "Oppenheimer." Culkin's performance stood out as the favorite from the start, especially after receiving previous accolades from the Golden Globes, BAFTA, and SAG Awards, ironing out his status as one of Hollywood's significant rising stars.
This marks not just the fulfillment of Culkin's career aspirations but is also noteworthy as it’s his first Oscar nomination. At 42 years old, Culkin delivered a heartfelt speech where he took the opportunity to praise fellow nominee Jeremy Strong, his co-star from the acclaimed HBO series "Succession." He humorously recalled how his wife, Jazz Charton, had promised him their fourth child if he won the Oscar, which added both warmth and humor to the evening.
"I want to thank my wife Jazz for promising me our fourth child if I won the Oscar," declared Culkin, clearly emotional about the recognition he received from the film industry.
The film "The Real Pain," directed and written by Jesse Eisenberg, follows two cousins from New York on their trip to Poland to discover their late grandmother's roots. The storyline delves deep, exploring their emotional challenges stemming from personal losses and generational trauma. Culkin's portrayal of Benji, who contrasts with his anxious cousin played by Eisenberg, creates dynamic tension and comedy throughout the film.
The film has been recognized not only for its narrative and acting but also showcases Eisenberg’s insight as it pays homage to his Polish lineage. "It's been truly magical working on this film with Jesse Eisenberg, and I owe so much to my fellow nominees," Culkin said, reflecting on the collaborative spirit during the film’s production.
Culkin's move from being overshadowed by his brother Macaulay Culkin's early fame to stepping up on his own has been inspirational. Known for his role as Roman Roy on "Succession," which aired to much acclaim, his transformation as he embraced acting full-time at age 35 has captured audiences' attention and critics alike. Once treated as merely competitive with his brother, the two could not be more different, and Kieran has carved out his own identity within the industry.
Owen Gleiberman from Variety praised Culkin's role, describing it as "nothing short of sensational," underpinning how deeply the audience connects with Benji’s struggles and sense of humor.
A notable shift occurred for Culkin when he accepted the role, as he acknowledged the film’s unique requirement for intense emotional commitment. "This is probably the best written role I've ever encountered. It felt almost tailor-made for me," he said, reflecting on the challenges and fulfillment the project brought.
The humor interspersed with serious moments helps tackle poignant issues surrounding grief and trauma effectively, making it more relatable than many heavier productions. Culkin’s character engages both comedic and serious tones, challenging taboos on grief and communication.
This transformative chance for Kieran Culkin emphasizes his remarkable growth over the years—from child actor to celebrated performer capable of nuanced portrayals and layered emotional depth. The excitement around his Oscar win signals not just his current success but the promise of what’s to come.
Having spent decades within the industry, Kieran's victory at the Oscars may prove to be the launchpad for many future projects where his talent can continue to shine. The quintessential story of the "underdog rising to the top," Culkin’s win is foreshadowing to the coming years where he may redefine expectations for himself and others.
It is hard to ignore the cultural significance of "The Real Pain" and how artists like Culkin are reshaping narratives around loss and identity through relatable storytelling. With such accolades, he stands as a beacon of inspiration for many others battling personal and familial challenges—never forgetting where you come from, and embracing who you are. Kieran Culkin’s Oscar win is not just personal triumph; it’s testimony of triumph within the arts and cinema, reiterative of how our stories bind us even through pain.