After stabbing an autistic boy, the sixteen year old troubled and pessimist Leland P. Fitzgerald is sent to a juvenile detention. His teacher and aspirant writer Pearl Madison gets close and tries to understand him, first with intention of writing a book, and later becoming his friend. Leland slowly discloses his sad vision of world.
The film begins with a flashback narrated by Leland P. Fitzgerald (Gosling), describing how he couldn't remember the details of the day that he killed a mentally retarded boy named Ryan Pollard (Michael Welch). Leland is arrested while the rest of the town reacts with shock to the senseless murder. Ryan's parents (Martin Donovan and Ann Magnuson), sisters Becky (Jena Malone) and Julie (Williams), as well as Julie's live-in boyfriend Allen (Klein) grieve the loss of their loved one. Leland's divorced mother (Lena Olin) is desperate to see her son, while his father, famous writer Albert Fitzgerald (Kevin Spacey), discovers his son's fate in a newspaper and returns home to be there for the trial.
