On an ordinary school day in California, a seemingly ordinary student named Leland Fitzgerald (Ryan Gosling) commits a devastating, inexplicable crime . . . and everything changes forever . . . not only for Leland but his family, friends and the teacher who becomes obsessed with trying to figure out why. Sent to juvenile hall to await trial, Leland says little to clear up the compelling mystery of how a young man of such promise could turn to cold-blooded violence; that is, until he meets Pearl (Don Cheadle), a compassionate but jaded teacher at the prison.
Pearl has never come across anyone like Leland. The son of famous author Albert Fitzgerald (Kevin Spacey), Leland had everything going for him. He seems like the last person on earth who would choose to commit murder, and as smart and insightful as Leland is, the first person to have a clear explanation for what he did. Even more than that, Leland appears to Pearl to be the perfect subject for a novel about the frailty and complexity of the human condition. If he can only get to the heart of what makes this kid tick, Pearl is certain his long-lived dream of becoming a writer as renowned as Albert Fitzgerald will be fulfilled. Defying prison protocol, Pearl arranges to meet with Leland in a series of secret counseling sessions.
As Pearl pushes Leland to disclose the full background of his crime, like a detective, he uncovers an increasingly intricate web of people involved in the story. There are Leland’s parents, the intellectually aloof Albert and his wife Marybeth (Lena Olin), who seem as stunned as anyone by Leland’s sense of alienation. Then, there is Becky Pollard (Jena Malone), both the victim’s sister and the troubled girlfriend who dumped Leland right before the murder, breaking his heart. The victim’s family –including Becky’s accomplished sister Julie (Michelle Williams) and her live-in boyfriend Allen (Chris Klein), as well as the murdered boy’s parents (Martin Donovan and Ann Magnuson) – bring yet another dimension to the story.