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Arts & Culture
03 March 2025

Kieran Culkin Wins Best Supporting Actor Oscar For A Real Pain

Culkin's emotional acceptance speech celebrates perseverance and family promises.

Kieran Culkin has taken center stage at the 97th Academy Awards, winning the Oscar for Best Supporting Actor for his role as Benji Kaplan in the critically acclaimed film A Real Pain. The ceremony, hosted by Conan O'Brien, celebrated Culkin's transformative performance and marked the culmination of his triumphant awards season, which saw him securing wins at the Golden Globes, BAFTAs, and the Screen Actors Guild Awards.

The 2025 Oscars unfolded with O'Brien delivering his signature humor, touching on this year’s notable films and actors. Kieran Culkin’s name echoed throughout the evening, as he gracefully navigated the stage to accept his award, representing not just his triumph but also the stories of underdog actors striving for recognition. His emotional win underscored the narrative of perseverance within the competitive world of Hollywood.

Culkin’s portrayal of Benji is described as both charming and deeply vulnerable, embodying the conflicted essence of his character on a family pilgrimage to Poland, tracing truths of their grandmother’s past during the Holocaust. Critics and fans alike praised his ability to balance humor with poignant authenticity, making his role one of the standouts of the year.

“I cannot believe this,” Culkin exclaimed during his acceptance speech, as the audience erupted with applause. He opened by acknowledging fellow nominee Jeremy Strong, saying, “By the way, Jeremy, you were amazing in The Apprentice. I’m not supposed to single anyone out; that's favoritism... but you were great.” His laughter-filled speech transitioned smoothly to thank his wife, Jazz Charton, charmingly reminding her of her promise to have another child if he won the Oscar. “I love you, Jazz. This is, I have to thank my wife for giving my favorite people in the world,” he quipped, leading to laughter from the crowd.

Throughout this awards run, Kieran Culkin has demonstrated both charisma and wit, with his speeches becoming highlights at each event. At the SAG Awards, he joked about the trophy's weight, saying, “I don't think there’s any way anyone can hold this for 45 seconds.” His candidness and humor have endeared him to fans and observers alike.

The Best Supporting Actor category has traditionally recognized some of the most impactful performances, embodying roles often overlooked yet integral to narrative depth. Culkin triumphed over strong contenders including Edward Norton for A Complete Unknown, Yura Borisov for Anora, and Guy Pearce for The Brutalist. His win is especially notable as it highlights the Academy's appreciation for nuanced performances within collaborative stories.

Culkin's success seems to come full circle after years of hard work and determination. With roots tracing back to childhood as part of the Culkin acting family, Kieran shared the screen with his brother Macaulay in classics like Home Alone. Yet, it wasn't until the hit series Succession catapulted him to stardom, earning him multiple nominations and acclaim, including last year's Emmy win for Lead Actor.

The narrative continues to focus on Culkin's transformative role within A Real Pain, where his character helps unearth familial stories intertwined with the Holocaust’s stark realities. Culkin's performance has not only showcased his growth as an actor but has also sparked conversations about mental health, utilizing his personal experiences to lend authenticity to his portrayal.

This Oscar win marks the zenith of Culkin's career, signifying not only personal achievement but also shedding light on Hollywood's often-meandering path for actors who refuse to give up. His next steps seem poised toward greater artistic endeavors as he expressed his desire to continue pushing boundaries through his craft.

To mark the evening, Culkin wore a custom Kwiat Fred Leighton brooch featuring emerald, peridot, and purple sapphire, symbolizing his family. The subtle tribute was as heartfelt as his words, reflecting the tight-knit support behind his success. Culkin’s victory not only serves as a personal milestone but raises awareness for the importance of family, resilience, and the art of storytelling.

With the Oscar win, Culkin edges closer to becoming part of exclusive circles, possibly eyeing the elusive EGOT status, already having won multiple awards, including the Emmy. This remarkable triumph at the Oscars reaffirms belief for those who aspire to succeed against the odds.

Hollywood may have its skeptics, but Kieran Culkin is living proof of dedication paying off, standing proudly on the award’s stage waving his Oscar — not just for himself but as inspiration for countless others chasing their dreams.

Stay tuned for more coverage on the 2025 Oscars as this dynamic actor continues to shape his legacy, and perhaps, his family.