Leland Fitzgerald (Ryan Gosling) is a quiet, shy sixteen year old who has commit a heinous murder. Leland is scorned by his community and is sentenced to serve time in a near by juvenile detention facility. Leland’s days are wasted and marred in monotony and boredom until he meets an aspiring writer and prison teacher, Pearl Madison (Don Cheadle). Madison believes that by becoming close with the boy and understanding his motives, he can write his masterpiece and change his life forever. In addition, Leland’s father is himself a world renowned writer, so the family’s name should propel the books sales. Madison gets more than he bargained for when he Fitzgerald become close and form an inseparable bond.