A man has one day to put his life in order before a long stretch in prison in this drama directed by Spike Lee. Monty Brogan (Edward Norton) is a man who came from a working class family in New York. Monty's best friends Jacob (Philip Seymour Hoffman) and Slaughtery (Barry Pepper) went on to distinguished careers as, respectively, a high school teacher and a bonds trader, but Monty took a different path and began dealing drugs. While Monty's trade has made him plenty of money, it hasn't brought him much respect from his family and friends, and while Jacob and Slaughtery have stayed in touch, Monty's lifestyle has led them to keep their distance. One night, Monty is relaxing at home with his girlfriend Naturelle (Rosario Dawson) when the police show up; Monty is arrested, and after a trial he's sentenced to seven years in prison. On his last day of freedom before he goes to jail, Monty tries to make amends with his father (Brian Cox) and goes out on the town with Jacob and Slaughtery. With both of his friends facing emotional crises of their own, Monty finds himself wondering where his life took a wrong turn and if there's any way left to redeem himself. Along the way, Monty begins to suspect that Naturelle may have turned him in, and he has to deal with Kostya Novotny (Tony Siragusa), an ill-tempered drug supplier who has unfinished business with him.