On March 2, 2025, the Dolby Theatre in Los Angeles hosted the 97th Academy Awards, a ceremony that celebrated global cinema and crowned Kieran Culkin as the winner of the best supporting actor category for his role in “A Real Pain.” At 42, the American actor, widely recognized for his portrayal of the irreverent Roman Roy in HBO’s “Succession,” took the stage to claim the coveted golden statuette, capping an impeccable awards season. Prior to the Oscar, he had already secured victories at the Golden Globes, Critics Choice, BAFTA, and SAG Awards, establishing himself as the clear frontrunner. His performance in the film, directed by Jesse Eisenberg and exploring themes of family memory and Jewish heritage, was hailed as the heart of the story, blending sharp humor with emotional depth that resonated with critics and audiences alike. Culkin’s win also marks a rare achievement: since Christopher Plummer in 2012, no actor had won this category without their film being nominated for best picture, underscoring the strength of his performance in an indie production like “A Real Pain.” In an emotional speech, he thanked the film’s team, Eisenberg, and his family, including his wife Jazz Charton and their two children, revealing a personal side that contrasted with the sarcasm of his signature roles.
Kieran Culkin began his career as a child, appearing in films like “Home Alone” alongside his brother Macaulay Culkin, but it was through bold choices in indie projects that he built a solid reputation in Hollywood. “A Real Pain” showcased his ability to balance levity and gravity, particularly in scenes addressing the Holocaust’s legacy.
The Oscar night wasn’t just about Culkin—it highlighted the power of supporting performances that elevated diverse narratives, with nominees like Edward Norton and Jeremy Strong also leaving their mark. Still, Culkin stole the spotlight with a role that had been celebrated since the film’s premiere at the 2024 Sundance Film Festival.
Journey of a versatile talent
Born on September 30, 1982, in New York, Kieran Culkin grew up in a family already under the spotlight due to his older brother Macaulay, the star of “Home Alone.” From an early age, he was on film sets, taking part in family-friendly productions and laying the groundwork for more complex roles. In the 1990s, he appeared in movies like “Father of the Bride” and “The Mighty,” but it was during his teenage years, with “The Cider House Rules” in 1999 and “Igby Goes Down” in 2002, that his talent began to shine. The latter earned him a Golden Globe nomination, an early sign he could move beyond being “Macaulay’s brother.” His preference for smaller projects and theater roles throughout the 2000s kept him out of mainstream attention, but it paved the way for his breakout success in “Succession,” where he played Roman Roy from 2018 to 2023, winning an Emmy and global acclaim.
In “A Real Pain,” Culkin brings to life Benji, a character reflecting on his Holocaust-survivor grandmother’s history during a trip to Poland with his cousin David, played by Jesse Eisenberg. The natural chemistry between the two, marked by improvised dialogue, was a standout, earning the film an 87% approval rating on Rotten Tomatoes after Sundance. Culkin’s performance, especially in moments like the train scene where he confronts his family’s Jewish past, was praised as a perfect blend of humor and melancholy, solidifying his shift from charismatic supporting actor to a major cinematic force.
Off-screen, Culkin keeps a low profile. Married to Jazz Charton since 2013, he is a father of two and often credits his family with keeping him grounded amid the awards season frenzy. His Oscar speech, referencing his kids’ school meetings, added a human touch that further endeared him to the audience.
The road to the golden statuette
The best supporting actor category at the 2025 Oscars was fiercely competitive, featuring performances that stood out in varied narratives. Edward Norton impressed as Pete Seeger in “A Complete Unknown,” bringing a restrained yet powerful energy to the Bob Dylan biopic, while Guy Pearce delivered an intense turn as a visionary architect in “The Brutalist.” Yura Borisov, from “Anora,” offered a raw and emotional portrayal of a young Russian, and Jeremy Strong, Culkin’s “Succession” co-star, brought a methodical Roy Cohn to life in “The Apprentice.” Despite the strong competition, Culkin entered the ceremony with an impressive track record: 15 wins from critics’ associations, including the Gotham Awards and New York and Los Angeles circles, plus victories at the SAG Awards on February 23, 2025, and the BAFTA in February.
Culkin’s frontrunner status wasn’t without discussion. Some debated whether his role in “A Real Pain” qualified him as a co-lead rather than a supporting actor, given his character’s weight in the story. However, the supporting category campaign prevailed, and his win was hailed as a historic moment. He became the first actor since 2012 to take this award without a best picture nomination for his film, a testament to his standout work in a movie that earned just two nods: supporting actor and original screenplay.
The awards season tested Culkin’s stamina, with dozens of appearances since January. His Critics Choice win on January 12, 2025, set the tone, with a speech blending humor and gratitude—traits that defined his Oscar moment as well.
The power of “A Real Pain” in indie cinema
Shot in Poland, “A Real Pain” blends personal storytelling with historical reflection, following two cousins tracing their grandmother’s Holocaust survival story. Directed and starring Jesse Eisenberg, the film premiered at the 2024 Sundance Film Festival, where it received a 10-minute standing ovation. Made on a modest budget, it grossed about 12 million dollars worldwide, a notable figure for an indie production without major studio backing. Filming in real locations like the Majdanek concentration camp and old Jewish cemeteries lent authenticity, while its minimalist score heightened the introspective tone.
The collaboration between Eisenberg and Culkin, friends since the early 2000s, was key to the film’s success. Scenes like the train confrontation, where Benji reflects on the disparity between modern comfort and ancestral suffering, were partly improvised, showcasing their mutual trust. Inspired by Eisenberg’s own Jewish roots, the story also sparked a 20% surge in demand for Poland travel itineraries featuring the film’s sites.
Beyond the numbers, the film’s sensitive take on the Holocaust legacy, paired with Culkin’s signature humor, made it a standout in a year dominated by blockbusters. With just two Oscar nods, “A Real Pain” proves indie cinema still shines at awards season.
Key moments in Culkin’s career
Kieran Culkin’s Oscar win is the pinnacle of a career spanning over three decades. His first notable role came at age 8 in “Home Alone” as cousin Fuller, but the 2000s saw him carve out his own path. “Igby Goes Down” in 2002 marked his shift to mature roles, while “Scott Pilgrim vs. the World” in 2010 showcased his comedic flair. His Emmy-winning run in “Succession” from 2018 to 2023 elevated his profile, building a global fanbase.
Here are some career highlights:
- 1990: Debut in “Home Alone” alongside Macaulay Culkin, at age 8.
- 2002: Golden Globe nod for “Igby Goes Down,” at 20.
- 2020: Emmy win for “Succession,” cementing his TV success.
- 2025: Oscar for “A Real Pain,” his first Academy Award.
Culkin also shone on stage, with roles like “This Is Our Youth” in 2014 reinforcing his versatility. His early focus on smaller projects built a foundation for the ultimate recognition with “A Real Pain.”