KIERAN CULKIN – earlier roles of the actor that are WORTH knowing

I think this is the moment in Kieran Culkin ‘s career when he can finally say he has stepped out of the shadow of his brother Macaulay. This was, of course, a shadow of a purely commercial and iconic nature, making it highly subjective. Kieran’s film portfolio is full of serious, dramatically refined roles that emerged in his adulthood. Macaulay, on the other hand, experienced a boom in popularity as a child, which did not carry through to his maturity. What survived, however, is a legend that Kieran has painstakingly built upon in his career over the years—albeit more slowly and with greater focus on artistic craftsmanship. The Golden Globe for A Real Pain is the first concrete recognition of these efforts in film (he had previously been awarded for his role in the series Succession). However, Kieran earned this recognition through roles like the ones mentioned below.

Fuller McCallister, Home Alone (1990), directed by Chris Columbus

His character is marginal and has little significance to Kevin’s story. However, one might interpret Fuller McCallister’s existence as a way to highlight how little Kevin matters to the entire family, especially on such an important day as their departure for Christmas vacation. Nevertheless, Kieran had already encountered the big world of cinema, barely touching it but learning invaluable lessons for the future—lessons that paved the way for today’s Golden Globe.

Kevin Dillon, The Mighty (1998), directed by Peter Chelson

Perhaps Kieran’s best childhood role, and maybe even one of his best overall? He played a character with a heart too large for his body, both literally and figuratively—a condition that made living in the real world difficult. Kevin created an alternate world for himself, pulling a socially ostracized friend into it, thereby saving not his physical life but his mental and emotional one. The journey with Kevin was portrayed by Kieran with extraordinary sensitivity.

Buster, The Cider House Rules (1999), directed by Lasse Hallström

While this wasn’t a major role, it complemented the array of characters in The Cider House Rules. At this stage, Kieran was still finding his footing as an actor. Perhaps he hadn’t yet realized that he would take on challenging personalities with debatable entertainment value. Note his facial expressions as Buster, his slouched posture, restrained and subdued movements, and the scene where he runs to Dr. Larch, lying in a child’s pose with a mask on—a moment transporting him to a better world.

Igby, Igby Goes Down (2002), directed by Burr Steers

The star-studded cast didn’t help this film financially, and it is rarely referenced now by viewers or critics. Perhaps this is because it’s another story of a cheaper “rebel by choice,” given the tropes commonly used in coming-of-age dramas. However, in Kieran’s filmography, it is an important entry. The tragedy he portrays here has a temporal quality that is not necessarily more mature but distinct—deeply relatable to anyone who wants to experience life intensely.

Jimmy Bartlett, Lymelife (2008), directed by Derick Martini

The film’s main protagonist is Scott, played by Rory Culkin, Kieran’s younger brother. Jimmy’s role should be considered as background support, stabilizing the protagonist’s situation formally rather than thematically. Lymelife is almost forgotten and certainly underrated. Kieran’s role might not be the most colorful, but it’s worth noting that he wasn’t intimidated by his brother’s presence. He focused on his craft, demonstrating professionalism and confidence before the camera—qualities that led to his recent Golden Globe.

Neil, Movie 43 (2012), directed by Peter Farrelly and Elizabeth Banks

One of the short sketches in this outrageous film takes place in a supermarket. Neil, a quirky cashier, has an intense conversation with his ex-girlfriend, unaware of a live microphone nearby. Strong phrases are exchanged, involving hickeys, face drenching, and inserting fingers in unspeakable places. However, Kieran delivers these lines with such commitment and dramatic seriousness that they resonate regardless of the content.

Roman Roy, Succession (2018–2023), created by Jesse Armstrong

A complex role that requires deeper understanding to appreciate. Roman Roy is a sarcastic, defiant, and rebellious individual who has almost pathologically learned to benefit from his own humiliation and the humiliation of others—whether as the perpetrator or victim. Roman delights in degrading others and is vulgar towards those beneath him. Beneath this brash exterior lies deep insecurity caused by his father, which permeates his work, personal life, and sexuality. It could be said that Roman has a father complex, which Kieran portrays with remarkable nuance.