Miles Cullen (Gould) is a bank teller realizes the bank is about to be robbed after noticing a Mall Santa casing the joint. Cullen secretly steals money from the bank before the robbery, and fakes giving it over to the robber when he finally makes his move. However, the robber, psychopathic career criminal Harry Reikle (Plummer), realizes this and starts trying to intimidate Cullen into giving him the money. This leads to a dangerous cat-and-mouse game between the two thieves.
Provides examples of:
- All Girls Want Bad Boys: Downplayed with Elaine, who winds up ditching the psychotic thief Reikle for the affable Gentleman Thief Cullen at the first opportunity.
- Ax-Crazy: Reikle is an unhinged psychopath with a propensity for violence.
- Bad Santa: Before his initial bank robbery, Reikle dresses as a mall Santa to disguise himself.
- Big Bad: Harry Reikle schemes to rob the bank that Miles Cullen works at, and when Cullen steals the money for himself, Reikle spends the movie trying to intimidate him into giving it back.
- Bittersweet Ending: Cullen manages to escape with the money, gets Reikle killed, and finally gets together with Julie, but Elaine is still dead.
- Chekhov's Gun: The silent alarm that goes off when $100 bills are removed, which Cullen uses to get Reikle killed.
- The Chessmaster: Cullen, who quickly proves to be a master of Xanatos Speed Chess.
- Deadpan Snarker: Cullen.
- Depraved Bisexual: Reikle's implied to be one. He wears eyeliner, sports long fingernails, dreams of Cullen, and dresses in drag in the finale.
- Faux Affably Evil: Reikle is polite, but it's paper-thin and barely masks the monster he really is.
- The Film of the Book: Adapted by screenwriter Curtis Hanson from Danish author Anders Bodelsen's 1969 novel Think of a Number.
- Gentleman Thief: Cullen is polite and affable, and always dresses in a suit (albeit because that's the wardrobe required of a bank teller).
- Out-Gambitted: Cullen consistently manages to outwit Elaine and Reikle, and even gets Elaine to turn against Reikle when he points out that she has no real reason to stay with him if he'll kill them both For the Evulz.
- Pop-Star Composer: The film's score was composed by Canadian jazz legend Oscar Peterson.
- Redemption Equals Death: Downplayed, since Cullen is also a thief, but Reikle murders Elaine after she turns against him and decides to help Cullen.
- Smug Snake: Reikle, who's nowhere near as clever as he thinks.
- Straw Misogynist: Reikle, who often shows a derogatory attitude towards women and on some occasions reveals an outright hatred of them that results in him doing some pretty horrific things to several women he encounters; he rapes and nearly kills a teenage girl at the start of the film and is wanted by the police for that, and it's heavily implied Reikle's done things like this before