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Derailed is a 2005 American thriller/drama film based on a James Siegel novel by the same name adapted by Stuart Beattie. The film is directed by Mikael Håfström and stars Clive Owen and Jennifer Aniston.

Plot

Spoiler warning: Plot and/or ending details follow.

The protagonist, Charles Schine (Clive Owen), is a married advertising executive in Chicago. The introductory scenes of the movie reveal that Charles' marriage is deteriorating due to the stresses of caring for a teenage daughter who is seriously ill with diabetes.

While on a commuter train, Charles encounters an alluring woman named Lucinda (Jennifer Aniston). The attraction is mutual, and the two begin meeting more frequently. Ultimately, the two are intent on consummating their affair in a shady hotel. Just as Charles and Lucinda are about to have sex, an armed man later named as Philippe LaRoche (Vincent Cassel) bursts into the hotel room, beats Charles and brutally rapes Lucinda. Charles and Lucinda agree not to report the crime, as they do not want their spouses to learn of the affair. Shortly after the incident, Charles is blackmailed by LaRoche, who demands money in order to keep quiet about the situation.

The attacker demands $20,000, which Charles pays by taking money from an account meant to provide for the daughter's medical treatment. But a month later, the attacker calls again, demanding $100,000 -- and he's calling from Charles' house. Charles rushes home to find LaRoche visiting with his wife and daughter, posing as a business associate.

Charles has a friend, Winston Boyko, who works in the mailroom at work (RZA) who has done jail time, and enlists him to help scare off LaRoche. Winston is a friend of Charles, and as he discusses with Charles about his stay in jail, he admits to killing a man while in prison. As they prepare to approach LaRoche in Winston's car, Winston shows Charles the shank (make-shift knife) he used in prison. He gives it to Charles for good luck. But LaRoche is a step ahead, and kills Winston in his car. The murder is almost discovered by a couple of corrupt cops flirting with a prostitute- and Charles barely escapes being implicated in the murder. Charles has to clean up the crime scene, so that he won't be suspected of the murder himself. He does this by driving the car into a nearby body of water.

The next day, Charles is questioned by a police detective, who is also Winston's uncle, about his coworker. Later, Charles receives a call from LaRoche -- he's got Lucinda at gunpoint, and will kill her if Charles doesn't bring the $100,000 immediately. Charles does. The payoff complete, he and Lucinda say a tortured goodbye.

That night, Charles confesses everything to his wife. She's not happy.

Before another meeting with the suspicious detective, where Charles plans to tell the whole story, he decides he first has to let Lucinda know. He stops by her office, where he discovers she's not who she said she was.

Charles learns that Lucinda was in on the scam from the beginning; it was a setup. Charles tracks Lucinda and LaRoche back to the hotel, where they're setting up another mark. Charles breaks in, a gunfight ensues and it appears that everyone but Charles dies. Charles slips away. On the way out - as the police are emptying the hotel safe - Charles sees his old briefcase. He reclaims it and finds that it still has his $100,000 in it.

The next day, Charles gets busted for embezzling at work (he scammed $10,000 to pay his coworker to help him), and is sentenced to community service, teaching at a prison. It turns out that LaRoche survived the gunfight, and is an inmate at the prison. He lures Charles into the laundry room, taunts him, only to find that Charles tracked him here on purpose, to finish the job. Charles stabs LaRoche to death. He claims he was attacked and acted in self defense, but the suspicious police detective from earlier, Winston's uncle, isn't so sure. He recognizes the shank as Winston's and does not turn in Charles.