25th Hour - Plot

Plot

A canary yellow vintage Super Bee pulls up short on a New York City street, and Monty Brogan gets out with his buddy Kostya to look at a dog lying in the road. The animal was mauled in a dogfight and Monty intends to shoot him but changes his mind after he looks him in the eye and decides to take him to a nearby clinic instead.

Fast forward to late 2002, and Monty is about to begin serving a 7 year prison sentence for dealing drugs. He sits in the park with his dog, Doyle, thinking of his last day of freedom. He plans to meet his childhood friends Frank and Jacob that night at a club with his girlfriend Naturelle. Frank Slaughtery is a hot shot investment banker on Wall Street and Jacob Elinsky is an introverted high school teacher from a privileged family, with a crush on one of his 11th grade students. He visits his father, James, a former firefighter and recovering alcoholic who owns and runs a bar, to confirm their plans to drive to the prison the following morning. Though Monty's drug money helped him keep the bar, James is full of remorse, and he sneaks a drink when Monty goes to the bathroom. Monty, facing himself in the mirror, lashes out in his mind against everyone else: all the New York stereotypes he can think of, from the cabbies to the firefighters, the corner grocers to the mobsters, as if he hates them all.

Monty sold drugs for Uncle Nikolai, a Russian mobster, along with Kostya. Kostya tries to persuade Monty it was Naturelle who turned him in since she knew where he hid his drugs and money. Monty refused to turn state's evidence against Nikolai but he's not sure what Nikolai will do when he meets him at the club that night. He remembers how he met Naturelle when she was 17, hanging around his old school, and how happy they were before he was arrested. He persuades Frank to help him find out if it was Naturelle who betrayed him.

When they all meet at the club, Jacob sees his student, Mary, and Monty invites her in with them. Monty and Frank talk about what kind of a future he can have after prison, and Frank says they can open a bar together, even though he told Jacob he believes Monty's life is over and he deserves his sentence for dealing drugs. Frank baits Naturelle by accusing her of living high on Monty's money, and not caring where it came from, but she reminds him that he knew as well and said nothing. Jacob, meanwhile, finds the courage to kiss Mary, but both of them appear to be in shock afterwards and go their separate ways. Monty and Kostya go down to talk with Uncle Nikolai, who gives Monty advice on surviving in prison. Then Nikolai tells him it was Kostya, not Naturelle, who betrayed him, and offers him the chance to kill Kostya in exchange for protecting his father's bar. Monty refuses, reminding Nikolai that he asked Monty to trust Kostya in the first place, and he tells them he's done, and that his father is done with them, and he walks out.

After they leave, he tells Naturelle that he's sorry he mistrusted her, and he has one last thing to do. He goes to the park with Jacob and Frank, and asks Jacob to look after Doyle. Then he admits that he is terrified of being raped in prison, and asks Frank to beat him, saying if he goes in ugly he might have a chance at survival. Frank refuses, and Monty tries to provoke him, until Jacob intervenes and Monty attacks him. Frank grabs Monty, who goads him into taking out his frustration in a fistfight, leaving Monty bruised and bloody, with a broken nose, and Frank in tears. Monty gets up and goes home.

Naturelle tries to comfort him, but Monty's father arrives to take him to Otisville. As his father drives him to the prison, James suggests they go west, into hiding, giving Monty one last vision of freedom. Once again Monty sees a parade of faces from the streets of the city, all the people he will miss; and together, they envision a future where Monty escapes imprisonment, reunites with Naturelle, starts a family, and grows old. As the fantasy ends, we see that their car has gone past the turn off to head west.