The film begins in medias res, with the suspects getting caught and being interrogated. Then it flashes back to three years earlier and the film continues forward from there, interspersed with occasional bits from the interrogation.
Ariane Felder is pregnant. This is all the more surprising since this examining magistrate is an old-fashioned single person. But even more surprising is the fact that, according to DNA tests, the father is no other than Bob, a criminal prosecuted for atrocious assault and battery. Ariane, who does not remember anything, tries to understand what happened.
As a young ne'er-do-well named Lightfoot (Jeff Bridges) steals a car, an assassin attempts to shoot a preacher delivering a sermon at his pulpit. The preacher escapes on foot. Lightfoot, who happens to be driving by, inadvertently rescues him by running over his pursuer and giving the preacher a lift.
Simon (McAvoy), an art auctioneer, becomes an accessory to the theft of a painting–Goya's Witches in the Air–from his own auction house. When a gang attacks during an auction, Simon follows the house emergency protocol by packaging the painting. The gang's leader Franck (Cassel) then takes the package from him at gunpoint. Simon attacks Franck, who delivers him a blow to the head that leaves him with amnesia. When Franck gets home, he discovers that the package contains only an empty frame. After ransacking Simon's apartment and trashing his car, the gang kidnaps and unsuccessfully tortures him. But he has no memory of where he has hidden the painting. Franck decides to hire a hypnotherapist to try to help him remember.
In the spring of 1969, Anthony Curtis (Larenz Tate) is about to graduate from high school. Anthony is not going to college, and needing to get away from home to find himself, he enlists in the U.S. Marine Corps shortly after graduation. He is sent to Vietnam, leaving behind his middle-class family, a pregnant girlfriend (Rose Jackson), and small time crook Kirby (Keith David), who is like a second father.
A deadly firefight and a fire aboard a ship docked in the San Pedro Bay leaves only two survivors: a Hungarian criminal named Arkos Kovaz hospitalized from severe burns, and a small-time con artist, Roger "Verbal" Kint (Kevin Spacey), a pathetic cripple. Separately, FBI agent Jack Baer (Giancarlo Esposito) and Customs agent Dave Kujan (Chazz Palminteri) arrive in San Pedro, lured by reports of a large cocaine shipment, and Kujan's personal vendetta against Dean Keaton (Gabriel Byrne), a formerly corrupt police officer who has since given up his life of crime but who was supposedly involved in the massacre. While Baer is at the hospital attempting to get security for Kovaz, Kovaz begins yelling in Hungarian, and mentions the name Keyser Söze, which stops and stuns Baer. As Verbal later explains, Söze has a near mythical and vengeful reputation, having killed his own family when they were held hostage by a Hungarian gang and then killing all but one of the gang members before disappearing underground, keeping his true identity secret by insulating himself from his agents, who usually do not know for whom they are working.
A group of grifters rip off their latest mark and celebrate, while de facto leader of the group Jake Vig (Edward Burns) explains the art of the con. When one of the four (Louis Lombardi) is found shot to death, the other three learn that the latest money they stole actually belonged to a local L.A. crime lord called The King (Dustin Hoffman). Jake proposes that the grifters work for the King and steal money from Morgan Price (Robert Forster), a rival who owns a bank.
Ty Hackett (Columbus Short), an armed service veteran, is now an employee of Eagle Shield security, as a member of one of their many armored car transport teams. Now the legal guardian of younger brother Jimmy (Andre Kinney), the Silver Star recipient struggles to make ends meet. In a bar after an armored car prank heist played on Ty, his co-workers recount several historical attacks on armored cars. It is explained that Ashcroft (Fred Ward), their immediate supervisor, was once involved in an ambush, becoming the only survivor as he single-handedly killed five assailants. This story was topped by "a better" one of an armored car jacking in '88, wherein the guards surrendered the funds they were escorting in order to prevent the killing of a fellow guard; it concluded in the safety of all the guards and escape of the hijackers. The thieves were never caught, and the crew speculates that the escort team staged the attack.
Benjamin Jahrvi (Fisher Stevens), now unemployed, is peddling sophisticated toy robots that he makes himself by hand on the street corners of New York City. One robot wanders away from his stand and by chance makes its way into the office of Sandy Banatoni (Cynthia Gibb), a scout for a major toy company. Sandy tracks Ben down and orders 1,000 of his toys. Overhearing this offer is con artist Fred Ritter (Michael McKean), who smooth-talks his way into becoming Ben's business partner in the deal and later acquires the funding Ben needs to get his assembly line started from a loan shark.
A cleaner goes into the office of a banker. He tells the staff to leave then proceeds to change into a suit and place a picture on the desk of two brothers. Lardier, a courier, arrives and the man proceeds to explain to him that he has several financial options available. However a cell phones rings and Lardier hands it over to the man. The caller, who is angry, shouts down the phone. Uncomfortable the man tries to leave but is shot with a silenced pistol several times by Lardier. The man who died was the brother of Cash.
During the worst recorded rainstorm in the history of the Midwestern United States, armored truck drivers Tom (Christian Slater) and his uncle Charlie (Edward Asner) collect the money from local banks affected by the rising flood waters. In the small town of Huntingburg, Indiana, which has been evacuated, Tom and Charlie drive into a ditch and become stuck, and Charlie calls dispatch to alert the National Guard. They are then ambushed by Jim (Morgan Freeman) and his gang of armed robbers, Kenny (Michael Goorjian), Mr. Mehlor (Dann Florek) and Ray (Ricky Harris). Kenny accidentally shoots Charlie dead, as Tom gets away with the $3 million in cash and hides it in a cemetery.
Parker and Longbaugh are at a sperm donation facility, where they overhear a telephone conversation detailing a $1,000,000 payment to a surrogate mother for bearing the child of Hale Chidduck. Parker and Longbaugh resolve to kidnap the surrogate, Robin, but their attempt escalates into a shootout with her bodyguards, Jeffers and Obecks. The kidnappers are able to elude the bodyguards, who are arrested.
Outside of Las Vegas, Michael (Kurt Russell), a recent parolee, stops at a run-down desert motel. There, he finds a boy named Jesse (David Kaye) stealing the air valve caps off his car's wheels and chases him, meeting his mother, Cybil (Courteney Cox Arquette) whom he later beds. Later that night he is picked up by four men, all dressed in Elvis costumes, Murphy (Kevin Costner), Hanson (Christian Slater), Gus (David Arquette), and Franklin (Bokeem Woodbine), and they set off the next day headed into a casino holding an Elvis convention intent on robbing it. Michael rigs the elevator while the others rob the cages and counting room, and after a grotesquely violent firefight, Franklin dies during their escape.
U.S. Coast Guard Lieutenant Jordan (Joey Forman) responds to a number of pleas for help from civilian pleasure boat sailors off the coast of Southern California. This type of event is typical of what the Coast Guard deals with on a regular basis, and is one of the reasons why Jordan has requested to transfer to a new station. He is handing over the reins to Ensign Tom Garland (Robert Morse), a polite but remarkably clumsy fellow who will now report to Commander Taylor (Don Ameche), a man who fought in World War II with Garland's father and holds him in high regard.