It is Monty Brogan's (Edward Norton) last day of freedom before he begins serving a seven-year prison sentence for dealing drugs. He plans to spend his last night of freedom at a club with his childhood friends Jacob Elinsky (Philip Seymour Hoffman) and Frank Slaughtery (Barry Pepper), his girlfriend Naturelle (Rosario Dawson), and his father, James (Brian Cox). Frank, Monty's best friend since they were both three, is an investment banker on Wall Street. Jacob is a quiet, dorky high school teacher who comes from a privileged background.
This is one of Spike Lee's most acclaimed films. It was second on AV Club's top films of the decade and is on the Roger Ebert Great Movies List.
- Awesome McCoolname: Naturelle Riviera. Lampshaded by Mary during a drunken Just for Pun moment.
- Big Applesauce
- Brick Joke: While rescuing the abused dog on their way to a drug deal, Monty gets bitten, prompting Kostya to make a statement referencing Murphy's Law, but he mistakenly calls it Doyle’s Law. Monty is confused until he realizes Kostya’s mistake. Later, we see that Monty has named the dog he rescued "Doyle".
Kostya: Always everything that can go wrong, go wrong. It's not just you and me anymore, when we go out... it's you and me and Doyle.
Monty: Who's Doyle?
Kostya: Doyle! Doyle's Law. What?
Monty: It's Murphy.
Kostya: Who is Murphy?
Monty: Who's Murphy? Who's Doyle! It's Murphy's Law..."whatever can go wrong, will go wrong"?
Kostya: Him, yes!
- Cluster F-Bomb: Monty gives a five-minute monologue in the mirror that is basically a "fuck you" to everyone in New York.
- Deadpan Snarker: Frank.
- Dream Sequence: Even if you really want it to be true, the sequence at the end where Monty leaves town, meets up with Naturelle again, and they grow old and have kids together is just a dream Monty has while in the car on the way to jail to serve his sentence.
- Extremely Short Timespan: See title.
- Facecam: Used in a deleted scene consisting of a montage of all of the main characters discussing what “sway” means to them.
- A Good Name for a Song: The title of the Fall Out Boy song "Champagne for My Real Friends and Real Pain for My Sham Friends" is from a quote said by Edward Norton’s character during his going-away party.
- Hit Me Dammit: Monty asks Frank to hit him so that he won't look too attractive in prison.
- I Take Offense to That Last One: This exchange:
Monty: You fat Russian fuck.
Kostya: Fat Ukrainian fuck!
- The Informant: At first, Monty suspects that Naturelle was the one who ratted him out to the DEA. Then he finds out it was really Kostya.
- Jail Bait/Jail Bait Wait: Mentioned by Frank and Jacob when Jacob mentions that he’s attracted to one of his students. Frank tells him that he only needs to wait seven months.
- The Mafiya: Uncle Nikolai, the mobster Monty and Kostya work for.
- The Man in the Mirror Talks Back: During Edward Norton’s "fuck you" monologue, his reflection is seen speaking, moving and reacting, whereas he isn't.
- Metaphorgotten: Kostya's full of these. There are plenty of notable moments in the opening scene, including the Brick Joke conversation above.
- Pet the Dog: At the beginning of the film, Monty spots an abandoned, injured and dying dog in the street. At first, he wants to shoot it in order to put it out of its misery…but once he sees that the dog still has the spirit to live, Monty rescues it and essentially adopts it.
- Post Nine Eleven Terrorism Movie: At the time Twenty Fifth Hour was released, it was amazingly risqué to show five minutes worth of a character's first hand view of Ground Zero being cleaned up. To be fair, considering the rest of the movie's downer tone, it was used devastatingly well.
- Prison Rape: A major fear discussed by Monty and his friends. Monty’s afraid that this will happen to him in prison, and his friends seem to think the same. Monty tells Frank and Jacob, "I need you to make me ugly," asking them to rough him up so that there’s less of a chance of him getting raped in prison because he’s a "pretty boy".
- Rage Against the Reflection: Monty has a long monologue into a bathroom mirror, complaining about all of New York until he finally lays into himself. He never actually attacks the mirror, but he comes as close as one can without.
- Teacher-Student Romance: There's a kiss between Jacob and Mary. It seems mostly to be a Hot for Student situation, though.
- Wastebasket Ball: Present in the scene where Frank is introduced.