A car pulls up at night on a
New York City street. Monty Brogan and his friend Kostya get out to look at an injured dog lying in the road. Monty intends to perform a
mercy kill but changes his mind after looking the dog in the eye. Years later, Monty is one day away from starting a seven-year prison sentence for drug dealing. On his last day of freedom, he walks the city with Doyle, the dog he rescued, and visits his old high school, where he played varsity basketball as a freshman. Later, he plans to meet childhood friends at a club — Frank Slaughtery, a boorish Wall Street trader, Jacob Elinsky, an introverted high school teacher, and his live-in girlfriend, Naturelle Riviera. In a flashback, Monty remembers the night he was arrested.
DEA agents raid Monty's apartment and, knowing where to look, quickly find the drugs he was selling for Uncle Nikolai, a Russian mobster. Kostya tries to persuade Monty it was Naturelle who betrayed him, since she knew where he hid his drugs. Monty visits his father, James, a former firefighter and recovering alcoholic, at his bar, which has been funded by Monty's drug money. James remorsefully sneaks a drink when Monty goes to the restroom. Facing himself in the mirror, Monty lashes out in his mind against New York ethnic groups, against corporate criminals, and against
Osama bin Laden before finally turning on himself for stupidly not giving up his drug business before he was caught. Frank and Jacob meet at Frank's apartment overlooking the
World Trade Center site. Jacob muses about seeing Monty again when he is released in seven years. Frank impatiently tells Jacob that, after this night he will never see Monty again. In a police interview, agents tell Monty that Naturelle is the one who sold him out. They seek to get him to turn on Nikolai by threatening the prospect of a long prison term, and of prison rape. Monty refuses. He recalls how he met Naturelle when he was hanging around his old high school. He asks Frank to find out if it was Naturelle who betrayed him. Outside the club, Jacob sees Mary, a student he is infatuated with. Monty invites her in, although she is underage. Frank and Monty discuss prison. Frank tries to be encouraging, but Monty is convinced he'll be a victim of rape and have no future when he's released. Mary flirts with Jacob, which causes him to follow her to a bathroom and attempt a kiss, but Mary is frozen in shock and Jacob quickly leaves, considering the consequences. Frank accuses Naturelle of living on Monty's money despite knowing its origins, and suggests it was she who ratted out Monty. Naturelle slaps him and leaves. Monty and Kostya go to see Nikolai, who gives Monty advice on surviving in prison. Nikolai reveals that it was Kostya who betrayed Monty, and offers him a chance to kill Kostya in exchange for protecting his father. Monty refuses, reminding Nikolai that the mobster was the one who told Monty to trust Kostya in the first place. Monty walks out, leaving Kostya to be killed by the Russian mobsters. Monty returns to his apartment and apologizes to Naturelle for mistrusting her. He hands Doyle over to Jacob in the park. He again admits that he is terrified of being raped in prison, whereupon he asks Frank to beat him, believing that he might have a chance at survival if he enters the prison ugly. Frank refuses, but Monty goads him into taking out his frustrations, and is left bruised and bloody, with a broken nose. Naturelle tries to comfort him as Monty's father arrives to take him to
Federal Correctional Institution, Otisville. On the drive to prison in upstate New York, Monty again sees a parade of faces from the streets of the city. As they drive up the
Henry Hudson Parkway, James suggests they take the
George Washington Bridge to go west, into hiding, and gives Monty a vision of a future where he avoids imprisonment, reunites with Naturelle, starts a family, and grows old. When the vision stops, they are past the bridge, still driving toward the prison. ==Cast==