10 Best Macaulay Culkin Roles of All Time
✦ Edited and fact-checked by Senior Staff Writer Randy Harward.
What’s your favorite Macaulay Culkin performance? Whether you know him as the face of ’90s nostalgia or for his quirky adult renaissance, few actors have defined a generation quite like he did. While his recent star on the Hollywood Walk of Fame cemented his legacy, his filmography has been iconic for decades.
We’re revisiting our original TikTok video to highlight his most unforgettable characters. Whether he’s setting traps for burglars or exploring darker adult themes, Culkin’s range is criminally underrated. Here are the 10 best Macaulay Culkin roles you need to watch.
1. Home Alone (1990)
Of course, the top spot belongs to Home Alone. Whether you love it or scroll past it every Christmas season, there’s no denying its place in pop culture. Kevin McCallister is the role that made Culkin a global superstar, and his performance is the perfect blend of precocious charm and slapstick brilliance. It’s a movie that never gets old, no matter how many times we watch Harry and Marv get outsmarted.
2. My Girl (1991)
Ready for a tearjerker? My Girl is a coming-of-age film that’s both funny and tragic. Culkin plays Thomas J. Sennett, the allergy-prone best friend to Anna Chlumsky’s Vada. Their chemistry captures the innocence of childhood friendship perfectly, making the film’s emotional climax hit even harder. Oh boy, grab the tissues.
3. Uncle Buck (1989)
Culkin’s comedic chops were on full display alongside John Candy and fellow child actor Gaby Hoffmann in this John Hughes classic. Before he was left home alone, Culkin was Miles Russell, the interrogator-in-training who grills his uncle with rapid-fire questions. It’s a hilarious performance that proved he could hold his own against comedy legends, convincing Hughes to write Home Alone specifically for him.
4. The Good Son (1993)
Don’t let the angelic face fool you. In this psychological thriller, Culkin sheds his cute image entirely to play Henry Evans, a disturbed boy with a taste for violence. Watching him as a psychopath opposite Elijah Wood is genuinely chilling. He delivers his lines with a calm, cold malevolence that makes you forget he was ever Kevin McCallister. It was a bold, risky career move that proved he wasn’t just a comedy actor.
5. The Pagemaster (1994)
In The Pagemaster, Culkin stars as a timid boy who takes shelter in a library and gets swept into a fantastical storybook adventure. He brings a touching vulnerability to the role, grounding the story even as it shifts from live-action to animation to interact with literary classics. It’s a major nostalgic trip for ’90s kids, and it had a surprisingly difficult video game.
6. Richie Rich (1994)
As the wealthiest kid in the world, Culkin brings the classic Harvey Comics character to life with style. The premise of a kid running a corporation and saving his parents is absurd, but that’s what makes the movie stand out. I still love the whole “Mount Richmore” chase sequence. Plus, Culkin lends a grounded sweetness to Richie that makes him likable despite his billions. Richie Rich is also notable as the final major film before Culkin’s long hiatus began in 1995, marking the official end of his child star era.
7. Saved! (2004)
In this cult classic teen satire, Culkin plays Roland, a cynical student at a strict Christian high school. As a wheelchair user with a sharp tongue, he steals almost every scene he’s in with his dry wit and rebellious attitude, providing the perfect counterbalance to the film’s religious absurdity. It remains one of his most underrated performances as an adult actor.
8. Party Monster (2003)
Party Monster is where Culkin shed his child-star image completely, portraying the real-life club kid and murderer Michael Alig. It’s a gritty, flamboyant, and disturbing look at the New York City club scene of the late ’80s and early ’90s. His performance is fearless, diving deep into the drug-fueled chaos of a very broken character.
9. American Horror Story: Double Feature (2021)
Culkin made a massive splash in the TV world with his role as Mickey, a struggling writer and drug addict in Red Tide. Critics and fans alike hailed his performance as the highlight of the season, praising his vulnerability and tragic charm. It proved that he still has serious acting chops and left us wanting to see him in more horror projects.
10. The Righteous Gemstones (2022)
Culkin joined the cast of this hit HBO comedy as Harmon Freeman, the estranged son of Baby Billy (Walton Goggins). His chemistry with Goggins is electric, and his deadpan delivery fits perfectly into the show’s chaotic world. It’s a brilliant reminder of his ability to steal scenes with subtle, quiet humor.
FAQ about Macaulay Culkin’s best roles
What is Macaulay Culkin's most famous movie?
Without a doubt, Home Alone (1990) is his most famous film. It grossed over $476 million worldwide and is considered one of the greatest Christmas movies ever made.
Did Macaulay Culkin win an Oscar?
No, Macaulay Culkin has not won an Oscar. But he was nominated for a Golden Globe for Best Actor in a Motion Picture – Musical or Comedy for Home Alone.
Why did Macaulay Culkin stop acting?
After a rigorous schedule of filming multiple movies a year, Culkin took a hiatus in 1994 to have a "normal" life and attend high school. He returned to acting in the early 2000s with roles in Party Monster and Saved!.
