Lorenzo "Shakes" Carcaterra (Jason Patric), Thomas "Tommy" Marcano (Billy Crudup), Michael Sullivan (Brad Pitt), and John Reilly (Ron Eldard) are four childhood friends who grew up in Hell's Kitchen, New York City in the mid-1960s. Hell's kitchen was an immigrant neighborhood and life was tough. Domestic violence was a daily occurrence, but the Kitchen also protected its own from outside criminals. During this time, the local priest, Father Bobby Carillo (Robert De Niro), plays a very important part in their lives and keeps an eye on them. They served as altar boys at the church. However, early on they start running small errands for a local gangster, King Benny (Vittorio Gassman). The boys also had a competition going on who could play the boldest prank. Mostly it was innocent stuff like sitting in the priest's chamber of the confession booth, or poking holes into walls to ogle at naked women changing clothes in the change rooms. On a summer day in 1967, their lives take a sharp turn when they almost kill a man after pulling a prank on a hot dog vendor. They accidentally roll the cart down a set of subway stairs, severely injuring an elderly man. As punishment, they are all sentenced to serve time at the Wilkinson Home for Boys in Upstate New York. Shakes is given six-to-twelve months, while the others are given 12-to-18 months. The juvenile center is full of hard-core offenders, with no method for rehabilitation. There, the boys are systematically beaten, abused, and sexually assaulted by guards Sean Nokes (Kevin Bacon), Henry Addison (Jeffrey Donovan), Adam Styler (Lennie Loftin), and Ralph Ferguson (Terry Kinney). These traumatic events change the boys and their friendship forever. Father Bobby visited the boys regularly, but Nokes warned them not to say anything else the reprisals would be severe. Father Bobby gives Shakes the strength to keep going. Mr. Carlson (John Slattery) is the English teacher at the facility and appreciates the interest that Shakes shows in the subject. Guard Marlboro (James Pickens Jr.) is the only one who tries to protect the boys a little bit from the brutality of the predators. When at the facility, the boys participate in Wilkinson's annual football game between the guards and inmates. Michael convinces inmate Rizzo Robinson (Eugene Byrd) to help win the game. Humiliated, the guards move the boys to solitary confinement for weeks, where they are systematically beaten. Rizzo does not survive, and his family is told he had died of pneumonia. In spring 1968, shortly before Shakes's release from Wilkinson, he suggests the boys publicly report the abuse. The others refuse, with Michael asserting that no one would believe them or care, and they vow to never speak of it again. The night before Shakes is released, Nokes and the other guards arrange a "farewell party", in which the four boys are brutally sexually assaulted worse than they have been before. Fourteen years later in 1981, John and Tommy, now gangsters, find Sean Nokes in a Hell's Kitchen pub. When John and Tommy confront him, he dismisses the abuse he put them through. They both shoot him dead in front of several witnesses. Mike, now an assistant District Attorney, arranges to be assigned to the case, secretly intending to botch the prosecution to use it as a means of getting revenge. Moreover, he and Shakes begin forging a plan to get their revenge on all the guards who abused them. Together with many of their lifelong friends, especially Carol (Minnie Driver), a social worker, and King Benny, they manage to carry out their revenge using information on all the Wilkinson guards compiled by Mike previously. Benny spreads the word not to touch Mike and forbids any hits on Mike for taking the case against John and Tommy. Mike says that all Juvenile records are destroyed after 7 years, so there is no link between them and the guards anymore. They hire Danny Snyder (Dustin Hoffman), a washed-up, alcoholic lawyer, to defend John and Tommy to make it seem as if the case is hopeless, allowing them to carry out their plan without being watched. Benny gets involved and 2 of the 4 witnessed change their minds about testifying against John and Tommy. Mike provides all the research to Danny to prove that one of the witnesses who testifies to have seen both John and Tommy walk out of the pub, was drunk at the time of the shooting. However, to clinch the case they need a key witness who can give John and Tommy an alibi. Shakes has a long talk with Father Bobby and tells him about the abuse they suffered at Wilkinson. Mike calls Ralph Ferguson as a character witness in court. Again, Danny has been provided a detailed list of questions to expose Ferguson and Nokes as serial abusers of kids at the juvenile facility. Ferguson breaks down under the strain of the questions and his oath and admits to all accusations against him and Nokes. After a few days of soul-searching, Father Bobby agrees to lie on the stand about where John and Tommy were on the night of the shooting; the priest swears under oath that they were with him at Madison Square Garden at a New York Knicks basketball game. As a result, they are acquitted. The remaining guards are also punished for their crimes: one, Henry Addison, is killed by the drug gang run by the older brother of Rizzo (who was informed by Benny about Addison's crimes against Rizzo), a boy killed years before in the Wilkinson Home; the other, Adam Styler, a corrupt policeman accused of extorting and killing a drug dealer, is exposed, and arrested. Mike and Shakes had provided all the evidence against Adam to a detective, who was Benny's cousin. After the case is over, Mike quits his job as an attorney and moves to the English countryside where he becomes a carpenter; John drinks himself to death and Tommy is eventually murdered, both within a few years of the acquittal.
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