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Plot Summary

Discover the intricate plot of Derailed (2005). From unexpected twists to emotional highs and lows, this detailed summary breaks down every moment to give you a deeper understanding of the film’s story.


Charles Schine, played by Clive Owen, is an advertising executive based in Chicago, whose intense story unfolds as an unidentified man documents it from a prison cell. A series of flashbacks reveal Charles’s turbulent home life, where he grapples with a crumbling marriage and the challenges of his daughter’s diabetes, which necessitates costly medication.

While commuting, Charles meets the captivating Lucinda Harris, portrayed by Jennifer Aniston, a married financial adviser. An undeniable attraction sparks between them, leading to frequent clandestine meetings. The tension culminates in a rendezvous at a shabby hotel, where their affair takes a dark turn. An armed intruder, later known as Philippe LaRoche, played by Vincent Cassel, storms in, violently assaults Lucinda, and leaves Charles battered.

In a pact of silence to protect their spouses from discovering the affair, they decide against reporting the incident. However, things escalate when LaRoche blackmails Charles, initially demanding $20,000 and subsequently increasing the ransom to $100,000 while threatening his family. Desperate, Charles confides in Winston Boyko, an ex-con portrayed by RZA, who proposes to intimidate LaRoche for a fee. In a moment of desperation, Charles embezzles $10,000 from his workplace to pay Winston.

Tragically, Winston is murdered by LaRoche, prompting an investigation led by Detective Franklin Church, played by Giancarlo Esposito. Just when things couldn’t seem worse, LaRoche contacts Charles and reveals that he has Lucinda at gunpoint, demanding the remaining sum. To save her, Charles uses funds set aside for his daughter’s medical expenses, bidding a heart-wrenching goodbye to Lucinda after handing over the money.

In a shocking twist, Charles discovers that the woman he fell for on the train was not Lucinda but Jane, a lookalike temp. Realizing he has been duped, he tracks Jane and catches her in a compromising position with LaRoche. Determined to reclaim his stolen $100,000, he confronts Jane and her accomplices at a hotel, leading to a gripping shootout where he emerges as the sole survivor.

Though he retrieves his money, Charles faces arrest for the embezzlement he committed to pay Winston. His sentencing involves six months of community service, during which he comes across a story about himself that was being penned at the film’s outset. The narrative takes a climactic turn when he discovers LaRoche, who survived their earlier encounter, leading to a final confrontation that leaves LaRoche dead at Charles’s hands.

Ultimately, as Charles steps into the outside world, he crosses paths with Detective Church once more. Although the detective harbors suspicions, he allows Charles to return to his family, setting the stage for a life forever altered by the choices he made.

Timeline

Track the key events of Derailed (2005) with a comprehensive timeline. Perfect for understanding the sequence of major plot points, this feature offers clarity on how the story unfolds.


Charles's Turbulent Home Life

Charles Schine, an advertising executive, struggles with his crumbling marriage and the pressures of his daughter's diabetes. The constant worry about his daughter's costly medication adds to the strain at home, creating a sense of desperation in his life.

Chicago

An Unexpected Meeting

While commuting, Charles encounters Lucinda Harris, a captivating married financial adviser. Their attraction is instantaneous, sparking a deep connection that will lead to a series of secret meetings.

Train

The Affair Begins

Charles and Lucinda commence an affair, meeting regularly despite the risks involved. Their relationship quickly intensifies as they indulge in stolen moments away from their spouses.

Shabby hotel

Violent Intrusion

The affair takes a dark turn when an armed intruder, Philippe LaRoche, bursts into their rendezvous. The attack leaves Lucinda assaulted and Charles severely battered, marking a point of no return for Charles.

Shabby hotel

The Pact of Silence

In a desperate attempt to shield their spouses from the truth, Charles and Lucinda agree to remain silent about the violent incident. Their decision sets off a chain reaction of fear and blackmail.

Blackmail Begins

Philippe LaRoche starts blackmailing Charles, initially demanding $20,000. As the pressure mounts, the ransom escalates to $100,000, heightening Charles's desperation as he fears for his family's safety.

Seeking Help

Desperate for solutions, Charles confides in Winston Boyko, an ex-con who offers to intimidate LaRoche for a fee. Feeling trapped, Charles embezzles $10,000 from work to pay for Winston's help.

Charles's workplace

Tragedy Strikes

Winston is brutally murdered by LaRoche, leaving Charles in a precarious position. The murder triggers a police investigation led by Detective Franklin Church, intensifying the stakes for Charles.

Chicago

The Final Demand

LaRoche reaches out to Charles, revealing that he has taken Lucinda hostage and demands the remaining ransom. In a heart-wrenching decision, Charles sacrifices funds meant for his daughter's medication to save her.

The Truth About Lucinda

Charles learns that the woman he was involved with, who resembled Lucinda, was actually named Jane, a lookalike temp. Frustrated and feeling betrayed, he tracks Jane down in a compromising situation with LaRoche.

Hotel

Confrontation and Chaos

In a tense showdown, Charles confronts Jane and her associates at a hotel aiming to retrieve his stolen money. The confrontation escalates into a shootout, where Charles tragically emerges as the only survivor.

Hotel

Facing Consequences

Despite retrieving his money, Charles faces legal repercussions for the embezzlement he committed. He is sentenced to six months of community service, reflecting the price he pays for his decisions.

Court

A Story Unfolds

During his community service, Charles encounters a narrative about himself, echoing the film's opening. This narrative leads him to a shocking discovery that brings his tumultuous journey full circle.

The Final Showdown

In a climactic return, Charles confronts LaRoche, who survived their earlier encounter. Their confrontation culminates in LaRoche's death, bringing closure to Charles's torment.

A Changed Man

As Charles steps back into the outside world, he encounters Detective Church once more. Although Church harbors suspicions, he allows Charles to reunite with his family, marking a new chapter in Charles's life forever altered by his choices.

Chicago

Characters

Meet the characters that bring Derailed (2005) to life. Dive into detailed profiles of the cast and their roles, exploring their motivations, relationships, and arcs within the story.


Charles Schine (Clive Owen)

Charles Schine is a complex character battling the demons of his personal life, including a failing marriage and the burden of his daughter's health issues. His initial charm and ambition give way to desperation as he navigates a harrowing situation involving infidelity and blackmail. Charles's choices, steeped in moral ambiguity, reveal the depths he is willing to plummet to in order to protect his loved ones.

👨‍💼 Executive 🥺 Father 😟 Desperate

Lucinda Harris (Jennifer Aniston)

Lucinda Harris is a captivating yet flawed character, caught in a web of attraction and danger. As a married financial adviser, her affair with Charles brings excitement but ultimately leads to significant peril. Lucinda's tragedy stems from her choices, as she becomes entangled in a violent confrontation that changes her life forever.

💔 Lover 😬 Complicated 🤔 Temptress

Philippe LaRoche (Vincent Cassel)

Philippe LaRoche is a menacing antagonist whose violent actions drive the film's conflict. His predatory nature reveals a dark side of humanity, escalating the tension surrounding Charles's precarious situation. LaRoche's ability to manipulate and coerce highlights the theme of evil lurking in ordinary situations, making him a formidable foe.

😈 Villain 🔫 Threat ⚠️ Manipulative

Setting

Uncover the settings of Derailed (2005), from iconic locations to the time period that shapes its world. See how these elements add depth and context to the movie’s narrative.


Time period

The film presents a contemporary setting where modern challenges intersect with personal crises. The prevalence of technology, financial pressures, and complex relationships reflect real-world issues that resonate with current audiences. Themes of deception and moral dilemmas are explored against this backdrop of modern society.

Location

Chicago

Chicago, known for its vibrant culture and stunning architecture, serves as the primary backdrop for Charles Schine's turbulent life. The city's bustling atmosphere contrasts sharply with the personal turmoil Charles faces, from his crumbling marriage to his involvement in a dangerous affair. Its urban landscape accentuates the intense psychological drama unfolding in Charles's life.

🏙️ City

Themes

Explore the core themes of Derailed (2005). From its commentary on social issues to its emotional undertones, delve into the deeper messages woven into the film’s story.


💔

Love and Betrayal

The theme of love and betrayal stands central to the narrative, as Charles's affair with Lucinda leads to devastating consequences. Their initial attraction quickly morphs into a cycle of secrets and manipulation, highlighting the fragility of trust in relationships. Ultimately, the choices made in the name of love lead to heart-wrenching sacrifices.

🔫

Crime and Consequences

Derailed explores how one man's desperate choices lead him deeper into a world of crime and violence. Charles's embezzlement and subsequent blackmail reflect the extreme lengths individuals may go to in protecting their loved ones. The film starkly illustrates the notion that crime often spirals out of control, resulting in unforeseen consequences.

😔

Desperation

Desperation is a prevailing theme, encapsulating Charles's downward spiral as he grapples with overwhelming pressures from his family and transgressions. The film examines how dire circumstances can compel individuals to make morally questionable decisions, often leading to tragic outcomes. Charles's struggles are a testament to the lengths one will go for hope and redemption.

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