Advertising executive Charles Schine's marriage to his wife Deanna is deteriorating, and his daughter Amy suffers from diabetes, requiring expensive medication. Charles' story is being written down by a man in a prison cell.
On a commuter train, Charles strikes up a conversation with Lucinda Harris, an alluring woman who is a married financial adviser. The two show each other photographs of their respective daughters. A mutual attraction develops, and the two begin meeting frequently. Ultimately, they decide to consummate their affair and wind up in a seedy hotel. An armed man—later identified as Philippe LaRoche—bursts into the hotel room, beats Charles, and brutally rapes Lucinda. Charles and Lucinda, not wanting their spouses to learn of the affair, agree not to report the crime. Shortly after, LaRoche contacts Charles, threatens to kill his family, and blackmails him into paying him $20,000. A month later, LaRoche calls again, this time demanding $100,000.
Charles explains his situation to his friend Winston, an ex-con who works as a repairman in his building. Winston agrees to scare off LaRoche for ten percent of the payout. Charles embezzles $10,000 from his company and he and Winston plot to get the drop on LaRoche at his specified meeting location. However, LaRoche surprises them, shoots Winston dead, and takes Winston's payout. Charles disposes of Winston's body and gives a false alibi when he is questioned about the murder by police detective Franklin Church, who also happens to be Winston's close relative. Later, Charles receives a call from LaRoche; he is holding Lucinda hostage and will kill her if he doesn't deliver the $100,000. Charles takes the money from an account meant for his daughter's medical treatment and makes the payoff to LaRoche and his partner Dexter, who works at the motel.
Detective Church questions Charles again after uncovering his friendship with Winston, putting mounting pressure on Charles to come clean about the blackmail. First, he goes to Lucinda's company to warn her and is introduced to the real Lucinda Harris. The woman he met on the train is Jane, a temp who had worked there briefly. He goes to Jane's apartment; it is actually in the process of being rented out. Seeing that Jane's photograph of her daughter was actually a cut out of a stock picture in a brochure, he realizes Jane was in on the scam.
Charles tracks Jane down and sees her kissing LaRoche, and later observes her seducing Sam Griffin, another unsuspecting businessman. He rents a room in the same seedy hotel as before and waits for Jane to ensnare her target and bring Sam to a hotel room. Determined to retrieve his stolen money, Charles knocks LaRoche unconscious outside the hotel room door, disarms him, and reveals to Sam the scheme Jane was about to set him up for. Dexter arrives to back up LaRoche and a gunfight ensues; nearly everyone is fatally shot but Charles, who watches Jane die, returns to his room and convinces the police he is merely a bystander. Before leaving the hotel, Charles claims his briefcase and gets back the money for his daughter's treatments.
Later, Charles' boss Eliot confronts him about the $10,000 he embezzled when he paid Winston. He is arrested for stealing from the company and sentenced to six months of community service, teaching in a prison. During one of his classes, he comes across the story about him written on one of the students papers. The writer instructs him to go to the laundry room. There, Charles finds LaRoche, who survived the gunfight. LaRoche threatens to continue to disrupt Charles' life, but Charles reveals that he has planned the encounter. He stabs RaRoche to death with a shank which Winston had given him.
Charles walks away from the encounter by claiming to Detective Church that LaRoche attacked him and he reacted in self-defense. Church is all but certain LaRoche's death was premeditated murder. However, he has pieced together LaRoche's crimes and is not inclined to seek justice for Winston's killer; instead, he allows Charles to return to his family.
Derailed opened in 2,443 theaters for an opening weekend gross of $12,211,986. The film made a domestic gross of $36,024,076 and an international gross of $21,455,000, giving it a worldwide gross of $57,479,076.
Derailed received mainly negative reviews and has a "rotten" score of 20% on Rotten Tomatoes based on 125 reviews with an average rating of 4.6 out of 10. The critical consensus states "With miscast stars, a ludicrous plot and an obvious twist, Derailed embodies its name all too aptly." The film also has a score of 40 out of 100 on Metacritic based on 34 critics indicating "mixed or average reviews."
Roger Ebert of the Chicago Sun-Times awarded the films two and a half out of four stars and believed that Owen's and Aniston's performances were intriguing. Ebert said, "Clive Owen was my candidate for James Bond, and can play hard and heartless rotters (see Closer), but here he is quiet and sad, with a sort of passivity. He lets his face relax into acceptance of his own bad fortune. Jennifer Aniston does that interesting thing of not being a stereotyped sexpot but being irresistibly intriguing. That works with a man like Charles. Happily married, in debt, worried about his daughter and his job, he would be impervious to a sexy slut."
- "Johnny" - Rular Rah
- "I Love You" - Thea Van Seijen
- "Sabotage" - Maurice Featuring HottWheelz
- "Winston's Theme" (Orchestral) - Edward Shearmur
- "50 Ways To Leave Your Lover" - Grayson Hill
- "Really Want None" - Free Murda
- "I'm Sorry" - Maurice
- "Charles' Theme" (Orchestral) - Edward Shearmur
- "Better Man" - Maurice
- "My Love" - Thea Van Seijen
- "Better Man" (Guitar Remix) - Maurice
- "Trouble" - Pink
The film was remade in Hindi as The Train and a Sinhala film adaptation titled Dakina Dakina Mal.
In 2010, the film was remade in Ghana by filmmaker Frank Rajah Arase as Temptation. It stars Majid Michel and Frank Artus.
Also a Tamil movie Pachaikili Muthucharam was adapted from the book.