Igby Goes Down

Igby Goes Down is a 2002 comedydrama film that follows the life of Igby Slocumb, a rebellious and sardonic New York City teenager who attempts to break free of his familial ties and wealthy, overbearing mother. The film was written and directed by Burr Steers, and stars Kieran Culkin, Claire Danes, Jeff Goldblum, Susan Sarandon, Amanda Peet, Ryan Phillippe, Bill Pullman, and Jared Harris. It was given a limited theatrical release through United Artists on September 13, 2002 in the United States.

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 classmates. 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., Igby first encounters Rachel Amanda Peet, his godfathers heroinaddicted trophy mistress. Rather than return to school, he escapes into the bohemian underworld of Manhattan, hiding out with Rachel and her performance artist friend Russel Jared Harris. Eventually, he and Rachel have sex. After being suspected and assaulted by D.H., he then hooks up with terminally bored, parttime lover, Sookie Claire Danes, only for her to later leave him for Ollie. ........

Source: Wikipedia