Plot
In 1975, after serving 5 years of a 30 year prison sentence, Carlito Brigante (Al Pacino) is freed on a legal technicality exploited by his close friend and lawyer, Dave Kleinfeld (Sean Penn). Carlito vows to be through with his criminal activities but is persuaded to accompany his young cousin Guajiro (John Ortiz) to a drug deal held at a bar. Guajiro is betrayed and killed by his suppliers and Carlito is forced to shoot his way out. Afterwards, Carlito takes Guajiro's $30,000 from the botched deal and uses it to buy into a nightclub owned by a gambling addict named Saso (Jorge Porcel) with the intent on saving $75,000 to retire to the Caribbean.
As nightclub co-owner, Carlito declines several offers for a business partnership with an ambitious, albeit obnoxious, young gangster from the Bronx named Benny Blanco (John Leguizamo). Carlito also rekindles his romance with his former girlfriend Gail (Penelope Ann Miller), a ballet dancer who moonlights as a stripper. Kleinfeld develops a love interest with Benny's girlfriend, Steffie, a waitress at Carlito's nightclub. Benny's frustration with Carlito's constant rejections boils over and he confronts Carlito one night at his table. Carlito publicly humiliates Benny, who reacts by manhandling Steffie. Fueled by his now extensive use of alcohol and cocaine, Kleinfeld brazenly pulls out a gun and threatens to kill Benny, but Carlito intervenes. Despite being personally threatened by Benny himself, Carlito lets Benny go unharmed; a decision which alienates Carlito's gangster friend and personal bodyguard Pachanga (Luis Guzmán).
Kleinfeld, who stole one million dollars in payoff money from his Italian mob-boss client, Anthony "Tony T" Taglialucci, is coerced into providing his yacht to help Tony T break out of the Rikers Island prison barge. Kleinfeld begs for Carlito's assistance in the prison break, and Carlito reluctantly agrees. Under cover of night, Carlito, Kleinfeld, and Tony T's son, Frankie, sail to a floating buoy outside of the prison barge where Tony T is waiting. As they pull Tony T aboard, Kleinfeld unexpectedly bludgeons him to death then slits Frankie's throat and dumps both of their bodies in the East River. Carlito immediately severs his ties with Kleinfeld and decides to leave town with Gail. The next day, Kleinfeld barely survives a retaliatory assassination attempt when he's stabbed in the chest at his office by two mobsters.
Carlito is apprehended by police and taken to District Attorney Norwalk's (James Rebhorn) office where he is played a tape of Kleinfeld making a deal and offering to testify to false criminal allegations against Carlito. Norwalk advises that he is aware of Carlito as an accomplice to the Taglialucci murders in an attempt to leverage him into betraying Kleinfeld to save himself, but Carlito refuses. Carlito visits Kleinfeld under police protection in the hospital, where Kleinfeld confesses to selling him out; Carlito warns Kleinfeld that he's crossed the line from being a lawyer to acting like a gangster, and other gangsters will treat him accordingly. Having noticed a suspicious man dressed in a police uniform waiting in the lobby, Carlito deftly unloads Kleinfeld's revolver and parts ways with him. The man turns out to be Tony T's other son, Vinnie (Joseph Siravo), seeking vengeance for his brother and father. Vinnie sneaks into Kleinfeld's room and executes him without incident because of Kleinfeld's empty gun.
Carlito then buys train tickets to Miami for himself and Gail, now pregnant. When he stops by his club to get the stashed money, Carlito is met by a group of Italian mobsters led by Vinnie. The Italians plan on killing Carlito, but he manages to slip out through a secret exit. The Italians pursue him throughout the city's subway system and into Grand Central Terminal where they engage in a gunfight. Carlito kills all of his pursuers except Vinnie, who is shot and killed by police attracted by the gunfire.
As Carlito runs to catch the train where Gail and Pachanga are waiting for him, he is ambushed by a disguised Benny, who shoots Carlito several times in the abdomen with a silenced gun. Pachanga admits to the dying Carlito that he is now working for Benny, only to be shot as well. Carlito hands a tearful Gail the money and tells her to escape with their unborn child and start a new life elsewhere. As he is wheeled away on a gurney, Carlito stares at a billboard with a Caribbean beach and a picture of a woman. The billboard then comes to life in his mind, and the woman, who is clearly Gail, starts dancing as Carlito slowly passes away.
Read more about this topic: Carlito's Way
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