25th Hour

The film begins with Monty Brogan and his friend Kostya (Tony Siragusa) saving a dog that he found abandoned in the street. As he drives away, the opening credits roll over shots of the Tribute in Light at the World Trade Center site. The film then cuts to the present (approximately four years have passed) and Brogan is walking the streets of New York with Doyle (the dog he saved). He goes to his old school, where he meets up with his best friend, English teacher Jacob Elinsky (Hoffman), and discusses a get-together at a local club planned later that evening. Elinksy then calls their mutual best friend, Wall Street trader Frank Slaughtery (Pepper).

Monty then goes home to his girlfriend Naturelle (Dawson) and they discuss the fact that this is his last night before prison. Through a series of flashbacks, we learn that he has been busted for being a drug dealer, and he is looking at seven years in Otisville prison.

Monty visits his father James (Cox), who blames himself for his son's plight, at his Irish pub in Bay Ridge, Brooklyn. Monty goes to the bathroom and sees profanity written on a mirror; this prompts a hateful rant against everyone in the city that ends with Monty condemning himself. He and his father then discuss whether it was Naturelle who tipped off the police about him.

Jacob goes to Frank's apartment and talk about Monty going to prison. Jacob can't believe it's happening, but Frank claims that he deserves it because he has become rich through the misery of others. He then says that after tonight, they'll never see him again. Jacob and Frank go to a Chinese restaurant and they both confront each other about how they don't live in reality. They both meet Monty and Naturelle at a bar before going to the club.

At the club, Jacob runs into one of his students, Mary (Paquin), who goes with them into the club. Monty and Frank discuss what will happen to him in prison, and Frank promises him that they'll open a bar together once he is released. Frank and Naturelle also discuss how Monty got to this position, but Frank accuses her of not doing anything because she got used to the life his drug money afforded. He then insinuates that it might have been her who tipped off the cops. Monty and Kostya then go to speak to a group of Russian mobsters, run by Uncle Nikolai (Levan Uchaneishvili), who gives Monty some advice on how to survive in prison. Then it is revealed that it was Kostya who sold Monty out. Monty decides to leave, asserting that he'll never come back and leaving Kostya at the hands of the gangsters.

While all this is happening, Jacob kisses Mary, but her stunned reaction shows Jacob that making a move on her was a mistake. He leaves, shellshocked.

They all leave the club and go to a park, where Monty gives Doyle to Jacob. Monty then admits that he is terrified of being raped in prison, and gets Frank to beat him up, saying if he goes in looking ugly he might have a chance at survival. Frank does it reluctantly, giving Monty a black eye and a lot of cuts and bruises to his face. Monty then leaves his friends for the last time, as Jacob confronts a hysterically sobbing Frank.

Back home, James arrives and says that he'll take him to Otisville. While Jacob and Frank are still at the park reflecting on all that has happened, Monty is on his way to prison. On the way he looks out of his window and sees all the people who he ranted against standing along the road, smiling at him. He then sees a little boy on a bus and they each write their name on the window.

As they come to the George Washington Bridge, James says that if Monty wants it, he will make a left turn, leave New York, and drive through the desert until they find a town, where Monty will make a new life for himself. He will never come back to New York, but after a few years he will send for Naturelle, and they will start a family. Many years later, Monty will gather his whole family together and he'll tell them the whole story and who he is and where he comes from. Then he'll ask them if they know how lucky they are to be here, because it came so close to never happening.

The film cuts back to the present, as Monty and James continue driving, heading north towards upstate New York with the George Washington Bridge in the background.