In Marin County, two gas company men are lured by a scantily-clad woman to a remote spot in Mill Valley and killed by Bobby Maxwell (DeVeren Bookwalter). Maxwell's gang, the People's Revolutionary Strike Force (PRSF), plans to use the gas men's uniforms and van as part of an ambitious series of crimes that will make them rich.
In World War II, British prisoners arrive by train at a Japanese prison camp in Burma. The commandant, Colonel Saito (Sessue Hayakawa), informs them that all prisoners, regardless of rank, are to work on the construction of a railway bridge over the River Kwai that will connect Bangkok and Rangoon. The senior British officer, Lieutenant Colonel Nicholson (Alec Guinness), reminds Saito that the Geneva Conventions exempt officers from manual labour.
Hank Grotowski (Billy Bob Thornton), a widower, and his son, Sonny (Heath Ledger), are corrections officers in a local state prison. They reside in Georgia with Hank's ailing father, Buck (Peter Boyle), a racist whose wife committed suicide.
On January 18, 1960, Frank Morris (Clint Eastwood) arrives at the maximum security prison Alcatraz, having been sent there after escaping from several other prisons. He is sent in to meet the warden (Patrick McGoohan), who curtly informs him that no one has ever escaped from Alcatraz. Eventually he meets his old friends, bank robber brothers John and Clarence Anglin (Fred Ward and Jack Thibeau), and he makes the acquaintance of the prisoner in the cell next to his, car thief Charley Butts (Larry Hankin). Morris befriends numerous other inmates, including English (Paul Benjamin), a black inmate serving two life sentences for killing two white men in self-defense; the eccentric Litmus (Frank Ronzio) who keeps a pet mouse and calls himself Al Capone, and the elderly artist and chrysanthemum grower Doc (Roberts Blossom).
Paul "Wrecking" Crewe is a former star pro football quarterback, who walks out on his wealthy girlfriend Melissa in Palm Beach, Florida. He takes her Maserati-engined Citroën SM without permission and leads police on a car chase, choreographed by Hal Needham. Crewe is eventually caught and sentenced to 18 months in Citrus State Prison.
John Matthews (Dwayne Johnson), owner of a construction company, receives a call from his ex-wife Sylvie Collins (Melina Kanakaredes). His estranged son Jason (Rafi Gavron) is being charged with distribution of narcotics; while Jason is not actually a dealer, his friend set him up in a sting operation to reduce his own sentence after being caught. Jason's charges carry a minimum of 10 years in prison. John feels responsible because he was not there for his son, and becomes desperate as he realizes that Jason may be killed before he finishes his prison sentence.
In 2024, inventor and professional computer programmer, Ken Castle (Michael C. Hall), has revolutionized the gaming industry with his self-replicating nanites that replace brain cells and allow full control of all motor functions by a third party. Castle's first application of this technology is a game called Society, which allows gamers to control a real person in a pseudo community (much like The Sims or Second Life). This allows players to engage in all manner of debauchery, such as deliberately injuring their "characters" and engaging in rough sex with random people. As a result, those who work as "characters" in Society are paid very well in compensation.
Miami liquor wholesaler Michael Gallagher (Newman), who is the son of a deceased criminal, awakes one day to find himself a front-page story in the local newspaper, indicating that he is being investigated in the disappearance and presumed murder of a local longshoreman union official, Joey Diaz.
The film is set in Washington state in 1964 and focuses on Selma Ježková (Björk), a Czech immigrant who has moved to the United States with her son, Gene Ježek (Vladica Kostic). They live a life of poverty as Selma works at a factory with her good friend Kathy (Catherine Deneuve), whom she nicknames "Cvalda" (which means "chubby" in Czech). She rents a trailer home on the property of town policeman Bill Houston (David Morse) and his wife Linda (Cara Seymour). She is also pursued by the shy but persistent Jeff (Peter Stormare), who also works at the factory.
Matthew Poncelet has been in prison for six years, awaiting his execution by lethal injection for killing a teenage couple. Poncelet, held in the Louisiana State Penitentiary, committed the crimes with a man named Carl Vitello, who received life imprisonment. As the day of his execution comes closer, Poncelet asks Sister Helen, with whom he has corresponded, to help him with a final appeal.
David Gale is a prisoner on death row in Texas. With only a few days to his execution, his lawyer negotiates a half million-dollar fee to tell his story to Bitsey Bloom, a journalist from a major news magazine known for her ability to keep secrets and protect her sources. He tells her the story of how he ended up on death row, revealed to the movie audience through a series of lengthy flashbacks.
Moltès, a killer in prison, plays the lottery every week and sends the tickets with Reggio, a guard, so that the latter's wife, Pauline, can have them validated. One day the ticket is a winner, but Pauline is at a party rally in Africa, carrying the ticket with her. Moltès wanting to recover his due, escapes and forces Reggio (the ball) to accompany him. However, he becomes the target of his nemesis, another gangster nicknamed "The Turk" (whose brother was killed by Moltès), and his bodyguard named Requin, a giant with teeth of steel.
In 1969 a mysterious man (Robert Redford) arrives at Wakefield State Prison in Arkansas. As an inmate, he immediately witnesses rampant abuse and corruption, including open and endemic sexual assault, torture, worm-ridden diseased food, insurance fraud and a doctor charging inmates for care. Brubaker eventually reveals himself—during a dramatic standoff involving a deranged prisoner who was being held in solitary confinement—to be the new prison warden to the amazement of both prisoners and officials alike.
Paul Armstrong (Sean Connery), a liberal Harvard professor opposed to capital punishment, is persuaded to go to Florida, to investigate the conviction of Bobby Earl Ferguson (Blair Underwood) for murder. Ferguson, a former Cornell University student, is a highly intelligent, charming, and articulate black man who was convicted of raping and murdering a young white girl. Armstrong must save him from being executed in the electric chair. Ferguson tells Armstrong that he was tortured by two police detectives to get a confession. As Armstrong digs deeper into the case, he discovers that Tanny Brown (Laurence Fishburne), the chief detective on the case, did indeed coerce Ferguson's confession.
On October 6, 1970, while on holiday in Istanbul, Turkey, American college student Billy Hayes straps 2 kg of hashish blocks to his chest. While attempting to board a plane back to the United States with his girlfriend, Billy is arrested by Turkish police on high alert due to fear of terrorist attacks. He is strip-searched, photographed and questioned. After a while, a shadowy American (who is never named, but is nicknamed "Tex" by Billy due to his thick Texan accent) arrives, takes Billy to a police station and translates for Billy for one of the detectives. On questioning Billy tells them that he bought the hashish from a taxicab driver, and offers to help the police track him down in exchange for his release. Billy goes with the police to a nearby market and points out the cab driver, but when they go to arrest the cabbie, it becomes apparent that the police have no intention of keeping their end of the deal with Billy. He sees an opportunity and makes a run for it, only to get cornered and recaptured by the mysterious American.