Carlito's Way is a 1993 gangster film based on the novels Carlito's Way and After Hours by Judge Edwin Torres. The film adaptation was scripted by David Koepp and directed by Brian De Palma. It stars Al Pacino, Sean Penn, Penelope Ann Miller, John Leguizamo, Jorge Porcel and Viggo Mortensen.
The movie's featured song, "You Are So Beautiful", was performed by Joe Cocker. The film is based on After Hours, but used the title of the first novel to avoid it being confused with Martin Scorsese's 1985 film of the same name, and focuses on Carlito's activities once he is released from prison. Carlito Brigante, a fictional Puerto Rican criminal vows to go straight and to live life as a law-abiding citizen. However, his past will not let him, and he unwittingly ends up being dragged into the same criminal activities that got him imprisoned in the first place. The film received a mixed response from critics, with a similar lukewarm result at the box office, but has subsequently been better received by both critics and film fans. Both Sean Penn and Penelope Ann Miller received Golden Globe nominations for their performances. A prequel called Carlito's Way: Rise to Power, based on the first novel, was filmed and released direct-to-video in 2005.
The story takes place in 1975 as Carlito Brigante (Al Pacino) is released from prison with the help of his close friend, and lawyer, Dave Kleinfeld (Sean Penn). Carlito makes a surprising announcement to Kleinfeld: he intends to go straight. Carlito visits his old neighborhood and is disturbed by how much has changed during his years in jail and how few people he knows. He runs into Pachanga (Luis Guzmán), a friend and fellow gangster, who runs down a laundry list of their friends who have either died or been sent to prison. Carlito, reluctantly, accompanies his young cousin, Guajiro (John Augstin Ortiz), on his way to a big drug deal. However, the gang have already killed Guajiro's boss, and betrays and kills him as well. Carlito ends up having to shoot his way out and once the dust settles he flees from the scene, taking the money from the deal. He buys into a nightclub owned by a gambling addict named Saso (Jorge Porcel) and acting as a nightclub promoter, begins to save every penny possible. He brings in his friend Pachanga as his right hand man and encounters Benny Blanco (John Leguizamo), a young gangster from the Bronx.
Away from the club, Carlito looks up Gail (Penelope Ann Miller), a former girlfriend, and they meet up with some awkwardness. Lalin (Viggo Mortensen), a former friend, arrives in the club wearing a "wire" in an attempt to get evidence against Carlito. This is dealt with quickly, and Carlito follows up on a comment made by Lalin about Gail in a stage show. Gail is discovered dancing, not in a play but rather on stage, in a strip show. Their relationship eases somewhat after that, as Carlito proves tolerant of it and some of the anxiety Gail had is lifted. Kleinfeld, now doing cocaine and drinking extensively, meets with a mob boss client, Tony "Tony T" Taglialucci (Frank Minucci). He believes that Kleinfeld stole a million dollars from him that was supposed to be used for a payoff. He gives Kleinfeld an ultimatum; help him break out of prison, or have a mob hit put on him. Meanwhile, Blanco grows frustrated with Carlito's rejection of champagne, and events escalate when Kleinfeld sparks a love-interest with Blanco's girlfriend, Steffie (Ingrid Rogers). After Carlito tells Benny what he thinks of him, Benny manhandles Steffie, spurring Kleinfeld to pull out a gun in Benny's face and threaten to kill him on the spot, causing chaos. Carlito is forced to take action and, with the help of Pachanga, takes Benny out the back where Pachanga and another bouncer beat him up. Carlito threatens to kill Benny if he is seen in the club again, and then orders Pachanga to let him go, as Carlito has rejected the violence of his youth.
Kleinfeld begs Carlito for his help with the escape attempt for Tony T. However, in the escape attempt, the increasingly erratic Kleinfeld kills both Tony T. and his son. Carlito realizes the severity of the transgression and decides that the only thing to do is to grab the money and leave town with Gail. Carlito is taken into Norwalk's office where he hears a tape of Kleinfeld offering to testify against Carlito. They know that Kleinfeld and Carlito were involved in the incident with Tony T., and in fact there was already an attack on Kleinfeld, which has put the lawyer in the hospital. The prosecutor offers Carlito a deal; testify against Kleinfeld and he can walk. Carlito refuses and goes to the hospital to learn the truth from Kleinfeld. On the way in he notices a suspicious man dressed as a police officer. Kleinfeld admits to selling out Carlito and while pretending to help Kleinfeld with his gun, Carlito deftly unloads it and leaves. The police officer turns out to be Tony T.'s other son, Vincent "Vinnie" Taglialucci (Joseph Siravo), who has come to finish off Kleinfeld. With his gun unloaded, Kleinfeld has no chance, and is fatally shot in the head. Carlito returns to the club intent on getting the money and getting out; once there, however, he is greeted by a group of Italian gangsters led by Pete Amadesso (Richard Foronjy), and Vinnie Taglialucci, who spotted Carlito earlier in the hospital.
The Italians know that he is involved, but before they have a chance to do anything, Carlito manages to slip out through a back way. A wild chase ensues where the Italians pursue him throughout the city subway system and into Grand Central Station, where the train Carlito and Gail will be taking is waiting. Carlito nearly manages to give them the slip, but is spotted and drawn into a wild gunfight where he manages to kill off all of his pursuers, except Vinnie. Vinnie is finished off by police. However, as he meets up with Pachanga and Gail, Carlito is ambushed by someone he did not expect: Benny Blanco, who shoots him in the abdomen with a silenced gun. Pachanga admits to be working with Blanco to set Carlito up, to lookout for his own future, just before he himself is shot by Blanco, who then runs off.
A dying Carlito hands Gail the money and tells her to escape with their unborn child, and live a new life elsewhere. The film ends with Carlito being wheeled away on a gurney as he stares at a billboard with a Caribbean beach and a dancing woman frozen in shot. He thinks about his wishes for Gail to get out and his own death. The billboard comes to life and the woman, who is Gail, starts dancing as he slowly closes his eyes.