- Directors: Burr Steers
- Producers: Lisa Tornell, Trish Hofmann, David Rubin
- Writers: Burr Steers
- Genres: Comedy, Drama
- Actors: Kieran Culkin, Claire Danes, Jeff Goldblum, Bill Pullman, Susan Sarandon
Kieran Culkin plays Jason “Igby” Slocumb, a sarcastic seventeen year old boy, rebelling against the oppressive world of his strict East Coast “old money” family. His father Jason (Bill Pullman) suffering from schizophrenia has been committed to an institution; Igby fears a mental breakdown like his father. His mother Mimi (Susan Sarandon) is self-absorbed and distant. Igby mockingly describes his ambitious older brother Ollie (Ryan Phillippe) as a facist or alternatively a Young Republican, and that he studies Neo-Fascism (Economics) at Columbia University.
Igby figures there must be a better life out there, and he sets out to find it, rebelling against his family at every opportunity. After happily flunking out of several prep schools, he ends up in a brutal military academy where he gets beaten by his fellow students. After escaping and spending time in a Chicago hotel courtesy of his mothers credit card Igby is sent to New York for the summer to his godfather D.H. Banes (Jeff Goldblum). While working construction for D.H. he first encounters Rachel (Amanda Peet) a “dancer who doesn’t dance”, his godfather’s heroin-addicted trophy mistress. Rather than return to school, he escapes into the bohemian underworld of Manhattan, hiding out with Rachel and her friend Russel (Jared Harris) “an artist who doesn’t paint”. He hooks up with terminally bored, part-time lover Sookie (Claire Danes), only for her to later leave him for his brother Ollie.
Director Burr Steers’ uncle Gore Vidal has a brief cameo as a Catholic priest.