The film centers around Jason "Igby" Slocumb (Culkin), a misanthropic and wealthy New York City teenager who attempts to break free of the clutches of his overprotective, drug-addicted mother (Sarandon). The film was warmly received by critics, many of whom drew comparisons to J. D. Salinger's The Catcher in the Rye.
This film provides examples of:
- Big Applesauce
- The Cameo: Gore Vidal as a priest.
- Driven to Suicide: Mimi.
- Hot Guy, Ugly Wife: H.D. and his wife Bunny.
- Ivy League for Everyone: Igby's older brother Ollie goes to Columbia.
- Jewish American Princess: Igby refers to Sookie as a "JAP" to her dismay.
- Trophy Wife: H.D. has a trophy mistress named Rachel (played by Amanda Peet) who he even invites to the same party as his wife.
- True Art Is Incomprehensible: Russell's performance art.
- Unfortunate Names: Igby and Sookie.