In 1990, Kieran Culkin made his screen debut in Home Alone. Culkin played Kevin’s (his brother, Macaulay Culkin) sweet, younger cousin, Fuller, who everyone was afraid to share a bed with due to his bladder issues after indulging in way too much soda before bedtime. It was an adorable film debut and Kieran certainly made a splash, so to speak. Nearly three decades later, he would land his acclaimed role on HBO’s juggernaut, Succession, as Roman Roy, the youngest son of Logan Roy (Brian Cox) vying for the family throne. Roman is best characterized as irresponsible, immature, and antagonistic, but he can deliver a one-liner like no other. He has been nominated for two Golden Globes and a Primetime Emmy for his role. Culkin has had a long list of roles since Home Alone, and it’s fun to look back and see hints of Roman Roy in some of his earliest projects. From small parts in big films to big parts in small films, and a dash of stage work, let’s take a look at some of his outstanding performances on his road from Fuller to Roman.
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Matty Banks – Father of the Bride
Just a year after Home Alone, Kieran appeared in the box office hit, Father of the Bride. Sharing the screen with legends such as Steve Martin, Diane Keaton, and Martin Short, Culkin is the ultimate scene-stealer. He plays the youngest son, Matty, who is wise beyond his years, which holds true for Culkin too. At a mere 9 years old, he holds his own in comedic timing with the maturity of a veteran actor. His car parking scene with his friend, Cameron, is an all-time classic.
Best Line – “How would you like to go through life with the name Cooper Banks-Mackenzie? The kid’s gonna sound like a law firm.”
Kevin ‘Freak’ Dillon – The Mighty
In The Mighty, an underrated indie film, Culkin stars as a terminally ill 12-year-old who tutors and befriends an older boy (Elden Henson) who could only be described as his polar opposite in every aspect. The film wasn’t financially successful, but it was a critical darling and seems to have gained more recognition over time. Culkin, again, impresses with his ability to mix deep, dramatic beats with sharp wit more than any 12-year-old actor should. His portrayal of ‘Freak’ is genuine in that he is a flawed person, but ultimately empathetic which makes his untimely demise all the more devastating.
Best Line – “Think of it as a business partnership: you need brains, and I need legs – and the Wizard of Oz doesn’t live in South Cincinnati.”
Tim Sullivan – The Dangerous Life of Altar Boys
Catholic schoolboys (and girls) being mischievous is a tale as old as time. However, in this film, Culkin and his group of trouble-making pals (including Emile Hirsch, Jake Richardson, Tyler Long, and Jena Malone) are just a bunch of teenagers who will do anything to avoid boredom. Culkin could easily make his character, Tim, one-note and stereotypical, but instead, he is layered with good intentions, even if they sometimes result in costly bad decisions. Working alongside Jodie Foster and Vincent D’Onofrio, Culkin fits in perfectly in this funny and poignant film.
Best Line – “Serious trouble beats serious boredom.”
Jason ‘Igby’ Slocum, Jr. – Igby Goes Down
Before Succession, this was probably Culkin’s most recognizable role. Nominated for a Golden Globe for his performance, Culkin portrays Igby, a modern-day Holden Caulfield type who is desperately trying to get away from his privileged upbringing to find meaning in the world. Culkin manages to prove, once and for all, that he can hold his own when leading a film, even with co-stars as big as Susan Sarandon, Bill Pullman, Jeff Goldblum, Claire Danes, and Ryan Philippe. The film itself is very quirky, and so is Igby, but even at his most obnoxious, Culkin makes it difficult to not root for him.
Best Line – “She’s a dancer who doesn’t dance. He’s a painter who doesn’t paint. It’s like the boho version of the Island of Misfit Toys.”
Justin Hammond – After Ashley
In this Off-Broadway play by Gina Gionfriddo in 2006, Culkin played Justin Hammond, a teenage boy navigating grief after he becomes semi-famous when the media gets a hold of his family’s tragedy. Culkin’s characterization of Justin proved that he was much more than a comedic actor. He showed his range by expressing his signature dark humor all the way to deep, emotional trauma. He was revered by audiences and critics alike, eventually being awarded an Obie for his performance.
Best Line – “Your decision to use my voice in your opening credits was very helpful to me. Financially helpful. I’m not using drugs anymore, but when I was, the royalty checks from your show helped cover the costs.”
Wallace Wells – Scott Pilgrim vs. the World
In Edgar Wright‘s adaptation of the graphic novel, Culkin really masters the art of smarm as Wallace Wells in this effortless portrayal of Scott Pilgrim’s (Michael Cera) roommate who is capable of being a good friend as well as giving the tough love that is so often needed. His unapologetic bluntness towards Scott is played with precision by Culkin who is the perfect counterpart for his romantic, and often whiny, friend, Scott. Wallace Wells is eternally likable and quotable and through it all, he roots for Scott, even though we can’t help but wonder if he’s just been hoping for chaos all along. With Culkin’s signature smug grin, it’s hard to tell.
Best Line – “I want to have his adopted babies.”
Rye Gerhardt – Fargo Season 2
A story of an ailing patriarch with three children who are competing for control of the dynasty, Culkin plays Rye, the youngest son who is a bit of a wild card. Sound familiar? Even with a similar premise to Succession, Rye Gerhardt is quite different from Roman Roy. Rye is volatile and leaves a trail of blood everywhere he goes. As with most characters in the Fargo universe, his time on screen is short but memorable. Culkin is able to deliver a fully formed malicious character in his episode that not only tells the audience about who he is, but a lot about the family he comes from. Rye’s presence is felt throughout the season and is the catalyst that drives the main narrative with Jesse Plemons and Kirsten Dunst’s characters.
Best Line – “That’s like Jupiter telling Pluto, ‘Hey, you’re a planet, too.’”
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