The 10 Most Underrated Macauley Culkin Movies, Ranked (From Least to Most Underrated)

Macaulay Culkin’s career stretches far beyond a single holiday classic. He started acting as a child in the late 1980s and worked across family adventures, thrillers, indie dramas, and ensemble comedies. His filmography includes lead roles and quieter supporting turns that show how often he was cast in different kinds of stories and budgets.

This list gathers ten films where he appears in roles that span precocious kids, troubled teens, and scene stealing side characters. You will find studio releases, indie projects, and even a filmed stage production. It gives a clear view of his collaborations with directors like John Hughes and Mary Lambert along with co stars such as John Candy, Anna Chlumsky, and Mandy Moore.

‘Getting Even with Dad’ (1994)

Culkin plays Timmy, a kid who disrupts a plan by his ex con father after a coin theft goes wrong. The film was directed by Howard Deutch and co stars Ted Danson and Glenne Headly. It was shot in and around San Francisco and centers on a scheme involving rare coins that draws in both family and police.

The movie opened in the summer of 1994 as part of a wave of kid driven live action comedies. Marketing leaned on Culkin’s star status at the time, and tie in promotions highlighted the father son premise. Home video and television reruns helped the film reach audiences that missed the theatrical run.

‘Richie Rich’ (1994)

Culkin headlines as Richie, the heir to the Rich fortune, in a story based on the Harvey Comics character. Donald Petrie directed, with John Larroquette, Edward Herrmann, Jonathan Hyde, and Joan Cusack in the cast. The plot follows a takeover attempt within the Rich empire and a rescue that uses high tech gadgets inside a mansion sized playground.

The production built elaborate sets for the Rich estate and used real locations like the Biltmore Estate to sell the world of a kid billionaire. The film arrived during the holiday season and later found a long life on cable. Its kid friendly gadgets and brand tie ins reflected mid 1990s studio family filmmaking.

‘George Balanchine’s The Nutcracker’ (1993)

This feature presents a filmed version of the New York City Ballet production, with Culkin appearing as the Nutcracker Prince. The project preserves Balanchine’s choreography and Tchaikovsky’s music for the screen. The cast includes members of the company and young performers who trained specifically for this staging.

The movie was designed to bring a seasonal stage experience to a wider audience. It was filmed with an approach that keeps the choreography intact while using close ups and edits to guide attention. Broadcast and home video releases made the production accessible far beyond the theater.

‘The Pagemaster’ (1994)

Culkin stars as Richard Tyler, a cautious kid who is drawn into an animated world of classic literature after seeking shelter in a library. Joe Johnston handled live action direction, while Maurice Hunt directed the animated sequences. Christopher Lloyd appears in live action and voices a character, and the voice cast includes Whoopi Goldberg, Patrick Stewart, and Leonard Nimoy.

The film combines live action bookends with a traditionally animated adventure that moves through genres like fantasy, horror, and swashbuckling tales. Production involved two pipelines that had to meet in composited transitions. The soundtrack and merchandising leaned into the library theme to engage young readers.

‘Party Monster’ (2003)

Culkin portrays Michael Alig in a narrative based on the New York club scene of the 1990s and the events that followed. The film was directed by Fenton Bailey and Randy Barbato and features Seth Green, Chloë Sevigny, and Dylan McDermott. It adapts material from a memoir and a documentary on the same subject.

The production was an independent feature with a modest budget and a focus on costume, makeup, and period music to recreate club culture. It premiered at festivals before a limited theatrical release. The film’s soundtrack and visual design drew on contemporary accounts of the era’s nightlife.

‘The Good Son’ (1993)

Culkin plays Henry, a boy whose behavior becomes increasingly alarming after his cousin moves in with the family. Joseph Ruben directed, and the cast includes Elijah Wood, Wendy Crewson, and David Morse. The story unfolds in a coastal New England setting that frames a series of escalations and confrontations.

The film’s production involved location shooting on rocky shorelines and a mix of practical stunts and visual effects. It released in the early fall of 1993 and generated attention for pairing two prominent young actors of the time. Home media releases included behind the scenes looks at specific set pieces.

‘Saved!’ (2004)

Culkin appears as Roland, a student who uses a wheelchair and navigates the social circles of a Christian high school. Brian Dannelly directed, with Jena Malone, Mandy Moore, and Eva Amurri in the ensemble. The story follows students dealing with faith, friendship, and senior year changes.

Filmed primarily in Canada, the production used real school locations and a modest budget with a focus on dialogue and character interactions. It premiered at festivals and then rolled out in theaters in limited release. The soundtrack features early 2000s tracks that fit the time and setting.

‘My Girl’ (1991)

Culkin co stars as Thomas J., a friend to Vada in a coming of age story set in a small town during the early 1970s. Howard Zieff directed, and the cast includes Anna Chlumsky, Dan Aykroyd, and Jamie Lee Curtis. The narrative follows family changes, summer activities, and the challenges of growing up.

The production filmed on location to capture a lived in neighborhood feel and used period details in wardrobe and props. The movie opened in late 1991 and connected with audiences who later discovered it on home video. A follow up film arrived with returning cast members and continued the story.

‘Uncle Buck’ (1989)

Culkin appears as Miles in a family comedy written and directed by John Hughes. John Candy stars as the title character, with Jean Louisa Kelly and Gaby Hoffmann rounding out the family dynamic. The plot centers on an unplanned visit that turns into a crash course in babysitting and household chaos.

The production shot in the Chicago area and used a mix of location homes and sets. The film became part of a larger wave of late 1980s Hughes projects and introduced Culkin to a wide audience. Specific sequences with quick fire questions and hallway gags became widely quoted in later broadcasts.

‘Jacob’s Ladder’ (1990)

Culkin plays Gabe, the son of Tim Robbins’ character, in a psychological drama directed by Adrian Lyne. The film follows a Vietnam veteran dealing with disturbing visions and fragmented memories that connect to his past. Elizabeth Peña and Danny Aiello appear in key supporting roles.

Production involved practical effects and in camera techniques to achieve unsettling images without heavy digital work. The movie opened in the fall of 1990 and later gained a strong afterlife on cable and home video. Its editing approach and visual design influenced many films and music videos that explored similar themes.

Share your own picks and where you first saw these movies in the comments.