In 1950, attorney Charles Phalen is contacted by an elderly man named "Brushy Bill" Roberts. Brushy Bill tells Phalen that he is dying and wants to receive a pardon that he was promised 70 years before by the Governor of New Mexico. When asked why he wants the pardon, Brushy Bill claims that he is really William H. Bonney aka "Billy The Kid", whom "everyone" knows to have been shot and killed by Pat Garrett in 1881. Phalen then asks if Bill has any proof that he is the famous outlaw.
In 1984, ten-year-old Tre Styles lives with his single mother Reva in Inglewood, California. After Tre gets involved in a fight at school, his teacher informs Reva that Tre is rather intelligent, but he is immature and lacks respect. Worried about Tre's future, Reva sends him to live in the Crenshaw neighborhood of South Central Los Angeles with his father, Furious Styles, from whom she hopes Tre will learn valuable life lessons. In Crenshaw, Tre reunites with his friends, Darrin "Doughboy" Baker, Doughboy's maternal half-brother Ricky, and Chris, their mutual friend. That night, Tre hears his father shooting at a burglar who tried to rob the house. Police officers arrive more than an hour later, and while the Caucasian officer is civil, the African-American officer treats Furious with disrespect and contempt.
A religious Las Vegas magician and wannabe gangster Buddy "Aces" Israel (Jeremy Piven) is hiding out in a Lake Tahoe hotel penthouse with his entourage. His agent and lawyer, Morris Mecklen (Curtis Armstrong), discusses a potential immunity deal with FBI Deputy Director Stanley Locke (Andy Garcia). Agents Richard Messner (Ryan Reynolds) and Donald Carruthers (Ray Liotta) learn that ailing Las Vegas mob boss Primo Sparazza (Joseph Ruskin) has issued a bounty on Israel worth $1 million; a mysterious assassin known only as The Swede has sworn that he will bring Israel's heart to Sparazza. A number of assassins also seek the reward, including Lazlo Soot (Tommy Flanagan), who specializes in disguises and impersonations; Sharice Watters (Taraji P. Henson) and Georgia Sykes (Alicia Keys), two hitwomen hired by Sparazza's underboss, Victor "Buzz" Padiche (David Proval); Pasquale Acosta (Nestor Carbonell), a calm torture expert and mercenary; and the psychotic neo-Nazi Tremor brothers, Darwin (Chris Pine), Jeeves (Kevin Durand), and Lester (Maury Sterling).
The film opens with a group of thieves led by Anthony Fait attempting to steal diamonds for a Frenchman named Christophe, who serves as the middleman for a mysterious employer. When Fait contacts Christophe, a Taiwanese Intelligence Agent named Su intercepts the conversation and attempts to identify the criminals.
During the film's opening credits, two bookies are separately ambushed and murdered by their unseen killers, and, elsewhere, a young man is killed by a sniper. In a bus terminal, a young man is approached by Goodkat (Bruce Willis), who tells the story of Max and the Kansas City Shuffle: two decades earlier, Max borrowed money from the mob to bet on a fixed horse race, only for the horse to die mid-race. To set an example to make sure nobody else would try to bet on a fixed race, the mob killed Max, his wife and young son Henry. Goodkat concludes that a "Kansas City Shuffle" is a misleading double bluff, and so tricks and kills the young man, before loading his body into a truck.
Anna Ivanovna, a British-Russian midwife at a London hospital, finds a Russian-language diary on the body of Tatiana, a 14-year-old girl who dies in childbirth. She also finds a card for the Trans-Siberian Restaurant, which is owned by Semyon, an old vor in the Russian Mafia. Anna thus sets out to track down the girl's family so that she can find a home for the baby girl, having meetings with Semyon, whom she initially regards as friendly. Anna's mother Helen does not discourage her, but Anna's Ukrainian uncle and self-described former KGB officer, Stepan, whom Anna asks for help with the translation of the diary, urges caution. Through translation of the diary, Anna comes to learn that Semyon and his ignorant therefore unstable son Kirill had abused the girl, addicted her to heroin, forced her into prostitution, and raped her. Ultimately, Anna realizes that the baby was fathered by Semyon (in several scenes it is made clear that Kirill is impotent and never had sex with Tatiana).
In 1931, the Bondurant brothers—Forrest, Howard and Jack—are running a successful moonshine business in Franklin County, in the Virginia Piedmont region. They use their gas station and restaurant as a front for their illegal activities, and their friend Cricket Pate assists them in their endeavors. One day, Jack witnesses mobster Floyd Banner shooting a competitor, and Jack and Floyd exchange looks.
The film begins with found footage from a Police dash camera of a car chase which ends in two police officers killing several gang members. This is all narrated by a monologue about what it means to be a police officer.
In 1988 in Brooklyn, New York, Bobby Green (Joaquin Phoenix) is the manager of the successful El Caribe nightclub in Brighton Beach that is frequented by Russian black market gangster and drug lord Vadim Nezhinski (Alex Veadov), and owned by Marat Buzhayev, Vadim's uncle and Bobby's boss.
Near the completion of his sentence in Sing Sing prison, Paul Vitti's life is threatened by assassins and corrupt guards while incarcerated. He fakes insanity and starts singing showtunes from West Side Story to get the attention of Ben Sobel, who previously hung up on him while attending his father's funeral. The FBI calls in Ben to see if Vitti is really insane. This appears to be the case, and the FBI approves Ben taking Vitti out of prison, into his own custody, for further therapy. On their way out in Sobel's car, Vitti reveals that he faked it. Needing some therapy himself after his father's death, a grieving Sobel talks Vitti into finding a regular job (as requested by the FBI). Vitti attempts to find a legitimate job (he tries a car dealer, a restaurant, and a jewelry store), but his rude manners and paranoia only complicate things further (which end up in him getting fired each time).
When Bobby Saint (James Carpinello) and Mickey Duka (Eddie Jemison) meet with European arms dealer Otto Krieg at the Tampa, Florida seaport, the FBI intervenes and Saint is killed while Duka is jailed. "Krieg", supposedly killed in the shootout, is actually undercover FBI agent and former U.S. Army Delta Force operator Frank Castle (Thomas Jane). Shortly thereafter, he retires from the FBI and attends a family reunion at his father's (Roy Scheider) oceanside home in Aguadilla Bay, Puerto Rico. Tampa crime boss Howard Saint (John Travolta) is enraged by the death of his son, and with right-hand man Quentin Glass (Will Patton) bribes the FBI for confidential information about "Krieg". Saint orders Castle murdered, and Saint's wife, Livia (Laura Harring), demands Castle's entire family be killed as well to "settle the score.
Michael Felgate is an English auctioneer living in New York where he manages the Cromwell auction house. He proposes marriage to his girlfriend Gina Vitale, but is shocked to be turned down. Gina tearfully explains that her father Frank and most of her cousins and uncles are gangsters deeply involved in a Mafia crime family, and she is worried that Michael may be sucked into their world. Michael retorts that he will not let this happen, but barely is their engagement party over before he is unwittingly involved in a money laundering scam, and soon the FBI takes an interest in him.
Rose Cooper is a San Antonio Police Department officer whose work ethic has made her too intense in her personal life. While out on a date, she scares the guy away after she defensively pulls a gun on him.
In the middle of the Great Depression, Clyde Barrow (Warren Beatty) and Bonnie Parker (Faye Dunaway) meet when Clyde tries to steal Bonnie's mother's car. Bonnie, who is bored by her job as a waitress, is intrigued with Clyde, and decides to take up with him and become his partner in crime. They pull off some holdups, but their amateur efforts, while exciting, are not very lucrative.
The Irish American fraternal twin brothers, Connor and Murphy MacManus, attend a Catholic Mass, where the priest mentions the fate of Kitty Genovese. Later, while celebrating St. Patrick's Day with friends, the two get into a bar brawl with three Russian mobsters who want to close the pub and take over the land it is built on. The two brothers try to reason with the mobsters, but they respond with violence, only to be quickly and embarrassingly dispatched by the brothers and other patrons of the bar. The next morning, two of the Russians seek revenge on Connor and Murphy, who kill the mobsters in an act of self-defense.