The narrative centers on Jack, a serial killer with an artistic flair, as he operates over a span of twelve years, showcasing the evolution of his heinous acts. Throughout this journey, he engages in philosophical dialogues with Verge, delving into themes of ethics and his own worldview.
1st Incident
While driving, Jack (portrayed by Matt Dillon) encounters a woman, Lady 1, stranded due to car trouble. As they share light-hearted banter, she jokingly insinuates he could be a serial killer. Agreeing to assist her, he takes her to his mechanic, Sonny. Despite fixing her tire jack, it falters again during their attempt to get the car running. As she requests another ride, Jack seizes the opportunity; he uses the tire jack to murder her before concealing her body within an industrial freezer he had secured just for such purposes. The woman's car is hidden partially out of sight in the bushes, lying in a secluded area where the police remain oblivious, lucky enough that it sits on the border of two states – an area often ignored.
2nd Incident
Jack adopts a new guise and knocks on the door of another woman, Lady 3, claiming to be a police officer with information regarding her deceased husband's pension. As the situation escalates, he poses as an insurance agent, offering her enticing cash promises. After luring her in, he chokes her but isn’t able to finish the job initially. When she awakens, he offers her a glass of water with disintegrated donuts in hopes of inducing choking, but to no avail. He ultimately resorts to strangulation before stabbing her directly in the heart. As the police become suspicious, represented by Ed Speleers, Jack hastily wraps her corpse and drags it to the freezer, leaving behind a gruesome trail of blood that, by sheer chance, the rain washes away later that night.
3rd Incident
In a chilling episode, Jack takes his girlfriend Jacqueline, along with her two sons, Grumpy and George, for a deceptive hunting lesson. In a calculated move, he murders the boys from a distance using a sniper rifle. Continuing his gruesome spree, he ultimately kills their mother and, leveraging his taxidermy skills, alters Grumpy's face into a grotesquely eternal smile.
4th Incident
After meeting Jacqueline (played by Riley Keough), whom Jack dubbed "Simple" due to his perception of her naivety, he fabricates tales of his murderous exploits, claiming to have killed sixty people as the notorious "Mr. Sophistication." Though she dismisses it as a mere boast, he makes his intentions clear by marking her with red circles, ultimately leading to her brutal demise. His depravity knows no bounds, as he goes so far as to sever and display one of her breasts on a police car, crafting the other into a grotesque wallet.
5th Incident
Jack finds himself orchestrating a macabre assembly, detaining six victims tied up in a row, intending to take them all out with a single bullet. However, misfortune hits as he discovers the bullets procured from Al aren't suitable. Desperation drives him to a man named S.P. ([David Bailie]), with whom he has a lethal encounter, ultimately acquiring the necessary bullet. In a moment of dark irony, he dons S.P.'s red bathrobe, hoping to elude the police who are closing in. Once captured, he embarks on a violent path while constructing a makeshift house out of bodies, mirroring the chaos in his mind.
Epilogue: Katabasis
Echoing Dante’s Inferno, Verge, who is revealed to be Virgil, guides Jack through branches of Hell. In a climactic moment, Jack discovers a broken bridge leading away from the depths of despair, while Verge warns him against the risks of navigating the treacherous cliffs. Ignoring the sage advice, Jack attempts the perilous climb but ultimately plummets into the fiery depths below, sealing his fate in a world forged by his own monstrous decisions.
