When Dean Stiffle (Billy Elliot's Jamie Bell) discovers the body of his best friends, Troy (Josh Janowicz), hanging in his bedroom, he doesn't bother telling any of the parents in his postcard perfect California neighborhood, figuring they wouldn't care. Dean shows no outward signs of remorse, and his father (William Fichtner), author of best-selling pop psychology books with titles such as The Happy Accident, treats his son with all the affection of a lab rat. "Dad," Dean deadpans, "If you write about me again in one of your stupid books, I'm going to kill you."

While Dean shrugs his way through high school wearing a psychic cloak of invisibility, his best friend Troy - the school's leading drug dealer - throws the community's carefully maintained psychotherapeutic balance into disarray when he hangs himself during on of his mother's pool parties. At school, in an effort to get their hands on Troy's stash, Dean's classmates Billy (Justin Chatwin), Crystal (Camilla Belle), and Lee (Lou Taylor Pucci) plot kidnapping scheme : they'll abduct Dean's younger brother, Charlie (Rory Culkin), and hold him for ransom in exchange for Dean retrieving Troy's pills. Only, the hapless gang kidnaps the wrong boy, snatching Charley Bratley (Thomas Curtis) instead. Son of divorced parents - police officer Lou Bratley (John Wilson), and interior decorator Terri (Rita Wilson) - Charley's dissapearance goes unnoticed by his mother, who is too consumed with the planning of her elaborate second wedding to town mayor Michael Ebbs (Ralph Fiennes), to realize her son has gone missing.

The kids and adults of Hillside live their lives entirely separately - like two opposing camps - a mournful divide played out in a visual scheme of sun-dappled, hallucinatory realism. Deciding both whether and how to negotiate these two worlds is Dean, a character whose very name purposely invokes the entire history of troubled teenage movie outsiders, from James Dean in Rebel Without A Cause to Christian Slater's J.D. in Heathers...