A pair of foster brothers named Charlie (Harrelson) and John (Snipes) work as transit cops in the New York City subway system. While John is doing pretty well for himself, Charlie is living in something of a downward spiral. Eventually Charlie winds up losing his job, getting berated by his brother, and gets the crap kicked out of him by a Loan Shark for unpaid debt. In an effort to pay off his debts and turn his life around, Charlie implements a plan to steal the "money train," an armored train carrying the New York Subway's weekly revenue.
This movie contains examples of:
- Action Girl: Grace is a tough, no-nonsense female cop who can keep up with her male coworkers.
- An Asskicking Christmas: The events of the movie happen on late December, with the heist occurring during New Year's Eve.
- Ax-Crazy: Torch.
- Berserk Button: For both the brothers it's calling Charlie a fuck up.
- Cool Train: The titular money train is a rolling vault.
- Cruel and Unusual Death: Torch is set on fire with his own gasoline and then run over by a train.
- Drunk Rolling: Charlie is a transit cop who plays a decoy drunk to foil a suspected heist, but a couple of prostitutes try to roll him. Grace, a female cop, has to intervene, pretending to be his enraged girlfriend.
- Evil Old Folks: All of the climax happens because Charlie encounters a little old lady who happens to be a pickpocket while he's on his way to pay the loan shark.
- Fanservice: Jennifer Lopez has a sex scene and her breasts are shown.
- The Gambling Addict: Charlie. The incredible hostility of Mr. Brown, the loan shark he owes money to, makes an important part of the plot.
- Happily Adopted: On the backstory, Charlie was adopted by John's family when he was a kid and (current vitriol aside), Charlie always looked up to John. He does say at one point, however, that he always felt his foster mother loved John best. He treats that as kind of inevitable, as John was her biological son, but apparently he does feel a little irked by it.
- High-Altitude Interrogation: Right after Charlie loses at cards to Mr. Brown, Brown's goons hold Charlie over the side of a building while they wait for John to arrive. Amusingly, when John learns that Charlie owes far more than he let on, John pretends to give the mobster permission to drop Charlie.Mook: Hey Charlie, let me get ya a fuckin' parachute!
Mr. Brown: Charlie, your brother had better get here soon or he's going to be an only child.
Charlie: [After John arrives] You brought the money, right?
John: Three hundred.
The Dragon: That motherfucker owes Mr. Brown fifteen thousand.
John: Fif- fifteen thousand?! You know what? [Holsters his gun] Drop him.
Charlie: He's kidding!
John: The hell I am. Drop the motherfucker.
- Hoist by His Own Petard: Part of Torch's death is setting himself on fire. Very fitting, considering his MO.
- I Will Punish Your Friend for Your Failure: After Charlie loses the money he was going to pay his Loan Shark with, (because some random pickpocketing lady stole it while he was riding the subway) he reaches the Despair Event Horizon and accepts the beating to come and the chance that he might well be killed by the loan shark's goons. The loan shark sees this and sees that threatening to hurt or kill Charlie is no longer going to get him paid, so threatens to go after John. This is what drives Charlie to attempt the heist.
- Patterson. The man oversees the running of the money train on time and with its full money reserve (which he goes as far as to call "his" money) as something more important than human lives. Early on he doesn't even apologizes for the train's guards shooting dead a small-time, unarmed crook that was running at them (while running away from John) and during the climactic heist his big plan to stop the train (although probably he believed it was the Godzilla Threshold, seeing that a thick steel barricade didn't stop it earlier) was to keep a passenger train on the same route and allow the money train to crash with it, even going so far as to radio the money train and tell John and Charlie that the resulting crash would be their fault. He also belittled Grace just for being a Latino woman, for which she gets her due payback by arresting him in the end for endangering innocent lives, and immediately suspects John and Charlie when the train runs several thousand short on a run that they were helping protect (and when it turns out that someone else did it, he doesn't apologizes and wants them fired for comments they did when he accused them of stealing).
- Mr. Brown the evil loan shark threatens to kill both brothers throughout the film unless Charlie pays up — he was okay with just hurting Charlie, but at the climax he threatens to kill John (and calls him the n-word as well) because Charlie had accepted his fate.
- Karma Houdini: The old lady pickpocket that took Charlie's money.
- Letterbox Arson: Torch pours gasoline through the exchange slot of a token booth, soaking the attendant and the compartment's interior. Torch then demands all the cash while thumbing a lighter. He gets the loot, then ignites the booth anyway, For the Evulz.
- Love Triangle: Foster brothers John and Charlie are both interested in their new coworker Grace Santiago. Trouble is that while she gets along with Charlie well enough and even calls out John for his initial reluctance to save Charlie near the end of the film, romantically speaking she's only interested in John.
- Nose Nuggets: The two brothers get even with a Jerkass who spat at Wesley Snipe's character by simultaneously punching him out and then firing off two snot rockets at him while he's down.
- Pre-Mortem One-Liner: Torch thinks he's doing this to John.Torch: Now... You see what happens when you play with fire?John: You get burned.
- Playing with Fire: Played straight by Chris Cooper's character, aptly named "Torch". He commits robberies with use of flammable materials, pouring gasoline into the station of a subway attendant and threatening to set them on fire if they don't give him the cash they have. He's so much of a psycho and a firebug, however, that he may go ahead and set off the fire anyway, just to see it burn.
- Politically Incorrect Villain:
- Patterson refers to John as a "Negro" the first time he has Charlie and John in his office, (which visibly pisses off John) and later mocks Grace by pronouncing her last name Santiago with an exaggerated accent.
- Mr. Brown calls John the n-word when talking to Charlie. Later, when John comes goes into Brown's club and beat the crap out of him and his goons to make them back off on Charlie, he gives Mr. Brown a little extra beating for that.
- Red Oni, Blue Oni: Charlie and John, respectively. Charlie is impulsive, emotional, and has control issues. John is by no means The Stoic, but he keeps far better control of himself, doesn't wear his heart on his sleeve, and has his life in much better shape than Charlie.
- Runaway Train: Oh, do tell. The money train becomes this for part of the climactic heist because John and Charlie, in a moment of desperation, deliberately sabotage the train so Patterson can't stop it and catch them... and after their sabotage, they can't stop it either. Patterson, not knowing this and assuming the thieves can still stop the train, decides to leave a passenger train on the same track, forcing them to either stop the train or crash and derail both trains. John and Charlie must then devise a way to make the train stop without it getting them or the innocent people on the passenger train killed.
- Salt and Pepper: The usual roles are inverted. John is the straight laced guy who has his life together, while Charlie is the wild card prone to making bad choices.
- Small Role, Big Impact: The loan shark Mr. Brown is only on screen for a couple of minutes with a handful of lines. If not for the debt that Charlie owes him and more importantly, his threat to start going after John because of Charlie's inability to pay his debt, the heist at the end of the film (which is the culmination of Charlie's downward spiral) would have never happened.
- Threat Backfire: Lampshaded and subverted by Mr. Brown the Loan Shark when he comes to threaten Charlie in the third act: he sees Charlie is completely tired of living and knows that threatening to hurt him at this stage wouldn't work, so he threatens to hurt Charlie's brother John instead, leading to Charlie deciding to perform the climactic heist on the money train.
- Turn the Other Fist: With a two-man twist. One brother will stop the other from hitting someone and pretend to play peacemaker... only for the second brother to use this opportunity to get in a sucker punch himself. Near the end of the movie Charlie and John stop each other from hitting Patterson... and then they both punch him together.John: [Stops Charlie from hitting a Jerkass cop who had insulted Charlie] Charlie, you're not going to hit him!
Charlie: Why not?
John: Because I'm going to hit him! (Lands surprise shot on the unprepared jerk ass)
- Vehicle Title
- Vitriolic Best Buds: Charlie and John, foster brothers. Their constant bickering is a Running Gag that runs as far as a good chunk of the credits, but when the going gets tough they work together.
- Yank the Dog's Chain: John goes into his savings and gives Charlie some money to pay off his gambling debts. Charlie's life is finally giving him a chance at a clean slate... and then Charlie legitimately loses the money to a pickpocket. Nobody believes him, the loan shark's goons kick the crap out of him, and John assumes he just gambled it away.