Derailed is a 2005 American thriller/drama film based on the novel of the same name by James Siegel. The film is directed by Mikael Håfström and stars Clive Owen, Jennifer Aniston, Vincent Cassel, Melissa George, Addison Timlin, Giancarlo Esposito, RZA and Xzibit. The film is set in Chicago.

Plot

The protagonist, Charles Schine (Clive Owen), is an advertising executive married to a schoolteacher in Chicago, whose tale is being written down in pencil in a notebook. The introductory scenes reveal Charles' marriage deteriorating due to both parents having busy careers, further stressed by their adolescent daughter's poorly controlled diabetes.

While on a commuter train, Charles encounters an alluring woman named Lucinda (Jennifer Aniston) when she pays for his forgotten fare. She is also married and has a daughter, whose wallet picture she shows him. Their mutual attraction grows, 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 threatens to kill Charles' family if he doesn't pay $20,000, which Charles promptly pays. But a month later, the attacker calls again, this time demanding $100,000—and calling from Charles' house. Charles rushes home to find LaRoche visiting with his wife Deanna (Melissa George) and daughter Amy (Addison Timlin), posing as a business associate and, much to his disgust, being exceptionally pleasant to his family.