Kieran Culkin has made history by winning the Academy Award for Best Supporting Actor for his standout performance in the film A Real Pain. His victory capped off an incredible awards season, further solidifying his place among Hollywood’s most talented actors. Culkin’s win came after an impressive series of accolades, including victories at the SAG Awards, BAFTA Film Awards, Critics’ Choice Awards, Golden Globes, and the Independent Spirit Awards. His performance in A Real Pain, where he plays a charming yet exasperating Jewish man touring Holocaust sites with his uptight cousin, was met with widespread praise and recognition, culminating in the ultimate honor at the Oscars.
In his heartfelt acceptance speech, Culkin reflected on the unforgettable moment following his 2024 Emmy win for Best Actor in Succession. During his Emmy speech, Culkin had jokingly asked his wife, Jazz Charton, to have a third child if he won the award. “After the show, we’re walking through a parking lot… and she goes, ‘Oh, God, I did say that!’” Culkin recalled. “I guess I owe you a third kid.” Culkin, always the joker, then turned to his wife and said, “Really, I want four.” Charton humorously responded with, “I will give you four when you win an Oscar.”
At the Oscars, Charton, seated in the audience, confirmed that she had indeed made this promise, prompting Culkin to address his wife directly. “I just have this to say to you, Jazz — love of my life, ye of little faith — no pressure. I love you. I’m really sorry I did this again, and let’s get cracking on those kids. What do you say?” Charton, laughing, mouthed a firm “No,” to the delight of the audience. This light-hearted exchange added a personal touch to Culkin’s emotional acceptance speech, showcasing his sense of humor and his loving relationship with his wife.
Culkin’s Oscar-winning role in A Real Pain is a significant career milestone, but it’s not his only major achievement. Culkin also received a nomination for the same award last year, competing against notable actors such as Yura Borisov for Anora, Edward Norton for A Complete Unknown, Guy Pearce for The Brutalist, and his Succession co-star Jeremy Strong. Although Strong’s performance in The Apprentice was widely acclaimed, Culkin’s wit and charm shone through, earning him the award after a competitive season. His win was also seen as a continuation of his successful journey through the awards circuit, with many considering him a frontrunner for Best Supporting Actor.
In his acceptance speech, Culkin didn’t shy away from delivering a memorable, free-associative address, one of the highlights of the season. He humorously thanked the film’s writer and director, Jesse Eisenberg, calling him a genius before playfully clarifying, “I would never say that to your face. I’m never saying it again. So soak it up.” He also praised his co-star Jeremy Strong, although his words were partially bleeped for language. “Jeremy, you’re amazing in ‘The Apprentice.’ I love your work, it’s f***ing…” he began, before quickly stopping himself. “I’m not supposed to single anyone out. It’s favoritism. Anyway — but you were great!” His candid, off-the-cuff remarks resonated with audiences and added to his reputation as one of the most entertaining and charismatic figures in Hollywood.
Culkin’s journey to this Oscar win is the culmination of years of hard work and dedication. Despite his early start in Hollywood, having appeared in films such as Home Alone and Father of the Bride, Culkin truly made his mark with his first leading role in 2002’s Igby Goes Down. In this film, he showcased his unique ability to blend comic timing with a sense of deep emotional vulnerability — a skill he later brought to A Real Pain in his portrayal of a character struggling with personal and familial conflict. His performance in A Real Pain was praised for its depth, with Culkin bringing a mix of charm and exasperation to the character, leaving a lasting impression on critics and audiences alike.
Interestingly, Culkin almost backed out of his role in A Real Pain just weeks before filming was set to begin. Culkin was hesitant about being away from his wife and two children for a month while shooting on location in Europe. However, it was actress and producer Emma Stone who persuaded him to stay, using a bit of emotional leverage. As Culkin recounted in an interview with Vogue, Stone told him, “If you don’t do it, the entire movie falls apart. But that’s not your responsibility. You shouldn’t feel that burden at all.” This convincing argument led Culkin to move forward with the project, and his decision paid off in a major way, resulting in his first-ever Academy Award.
Culkin’s Oscar win marks the culmination of an extraordinary career that began in his youth and has blossomed into a series of acclaimed roles. As he continues to showcase his talent, audiences can expect more unforgettable performances from the actor who has mastered both dramatic and comedic roles. With his remarkable career trajectory and his undeniable charm, Kieran Culkin has solidified his place as one of the most versatile actors of his generation.
