A group of thieves steal a rare gem, but in the process, two of the men double cross the leader of the thieving group, Patrick (Sean Bean), and take off with the precious stone. Ten years later, prominent psychiatrist Nathan Conrad (Michael Douglas) is invited to examine a disturbed young woman named Elisabeth (Brittany Murphy). Patrick immediately kidnaps Nathan’s daughter, forcing Nathan to attempt to get Elisabeth to reveal a secret number which will ultimately lead Patrick to the whereabouts of the precious gem that has eluded him.

Dalton is an expert “cooler” — a barroom bouncer who can break up fights without getting himself killed in the process. Frank Tilghman, the owner of the Double Deuce in Jasper, Missouri, has hired Dalton away from a bar in Memphis, because Tilghman needs someone who can handle the nightly outbreaks of violence at the Double Deuce, and teach the rest of the Double Deuce’s bouncers how to handle it. There’s even a cage protecting the bar’s band from the customers. The band is led by Dalton’s old friend Cody, who is blind. Dalton is injured on his first night on the job and is treated by Elizabeth “Doc” Clay, the local doctor. Dalton and Doc soon fall in love with each other, and this angers Brad Wesley, a crime boss that Doc was once involved with — and may still be involved with. Wesley is also responsible for a lot of the violence at the Double Deuce, and for some time, Wesley has had the sheriff in his pocket, giving him complete control of the town of Jasper. Wesley is out to get rid of Dalton, who has already made some friends in Jasper — Dalton has rented a room from a man named Emmet, and has befriended local auto parts store owner Red Webster, and has also befriended Pete Stroudenmire, the owner of Stroudenmire Ford, a local car dealership. Wesley, who wants money from these people, has his henchmen burn down Red’s store, run a big foot truck through the showroom of Pete’s dealership, and set Emmet’s home on fire. Dalton is pleasantly surprised when his mentor and old friend, legendary cooler Wade Garrett, arrives in town and helps him beat up the guys who are vandalizing Tilghman’s liquor shipment because Wesley wants to be the one to supply Tilghman’s liquor, and take money from Tilghman. A couple of days after Wade’s arrival, Wesley has Wade murdered in order to get a point across to Dalton. In retaliation, Dalton storms Wesley’s mansion, with every intention of freeing the town from Wesley.

New York City homicide detective Vincent LaMarca has forged a long and distinguished career in law enforcement, making a name for himself as a man intensely committed to his work. But on his latest case, the stakes are higher for Vincent—the suspect he’s investigating is his own son. He and Joey have been painfully estranged ever since Vincent divorced his wife and left the decaying boardwalks of Long Beach, Long Island for the anonymity of Manhattan and a successful career with the NYPD. He lives his life in solitude, keeping his girlfriend at arm’s length; the closest relationship he maintains is with his partner, Reg—and Vincent makes sure that stops at the precinct door. As long as Vincent lives in the protection of the present, he doesn’t have to deal with the pain of his past—or his sorrow over his broken relationship with Joey. But this murder investigation is drawing Vincent home to Long Beach, the self-proclaimed City by the Sea, where the past has been waiting for him to return. The agonizing memory that has tortured him all his life—the death of his father, a convicted murderer who was executed when Vincent was just a boy—still plagues him. In the course of the investigation, he discovers that his own unresolved pain and failures as a father have deeply influenced Joey’s life, and now his 18-month-old grandson may be fated to follow their self-destructive paths.

Gigli, a lowly and inept hitman, is assigned a job by the mob to kidnap a mentally retarded brother of a California district attorney. Gigli abducts the brother from his mental hospital and holds him hostage in his apartment. Ricki, a “lesbian assassin”, is sent to oversee Gigli’s job and make sure he doesn’t screw it up. Comedic high jinks ensue as the two go on the lam and start to fall in love.

“Sin City” is Four stories inter-weaved telling tales of corruption in Basin City. The First Story (The Customer is always right)is short, and is based on the depression of women that they need to pay a man to feel loved when they commit suicide. The Next Story is Part 1 of “That Yellow Bastard” starring Bruce Willis as a cop who needs to save a young girl from being raped. The Third Story (The Hard Goodbye) features Mickey Rourke and his revenge on a heartless killer who murdered his one-night stand. The fourth story (The Big, Fat Kill) stars Clive Owen as a man who must dispatch of a cop’s body, but it will be a tough ride to do it. Following that are two conclusions to Sin City, the ending of “That Yellow Bastard” which is set 8 years later, and a short story that ends Sin City.

Childhood friends Jimmy Markum (Penn), Sean Devine (Bacon) and Dave Boyle (Robbins) reunite following the death of Jimmy’s oldest daughter, Katie (Rossum). Sean’s a police detective on the case, gathering difficult and disturbing evidence; he’s also tasked with handling Jimmy’s rage and need for retribution.