Carlito Brigante (Al Pacino) is released from jail after serving five years of a much longer stretch. He vows to go straight and to live life as a fine, upstanding citizen. He even rekindles a romance with his ex-lover (Penelope Ann Miller). However, Carlito’s associates cannot seem to leave him in peace…his nephew involves him a pool-room gunfight, his lawyer (Sean Penn doing his best Dershowitz impression) asks him for “favors” which spiral out of control, and even an old friend tries to get him into trouble with the law. Carlito decides to make a run for Florida and the promise of a new life, but has one final dramatic escape to make from some hoods who believe (wrongly) that he was behind the murder of their boss. John Leguizamo gives a great turn as Carlito’s nephew.
Director Brian De Palma wanted to shoot the climax of the film at the World Trade Center in New York but it was the target of a bombing, and he had to shoot it in “another railway station again.” (De Palma’s The Untouchables (1987) also featured a scene at a railway station.)
The name of Carlito’s (Al Pacino’s) nightclub is “El Paraíso”, the same name as the food stand that Pacino’s character operated in Scarface (1983).
The exterior of the hospital where Carlito visits his bedridden attorney is the same one where Vito Corleone is taken in The Godfather (1972), also starring Al Pacino.
Sean Penn took the role of David Kleinfeld just for the money so he could use it to fund his second film The Crossing Guard (1995).
Carlito’s Way is adapted from the novel “After Hours” by ‘Edwin Torres’. However, it took the title from Torres’ first novel about the rise of crime boss Carlos Brigante so that it would not be confused with Martin Scorsese’s New York club-based comedy-drama, After Hours (1985).
The word “fuck” is said a total of 139 times.
Al Pacino had difficulty with his scenes with Jorge Porcel, who played Saso, the club owner. The actor, who was primarily a television comedian, spoke no English and learned his lines phonetically.
Directors John McKenzie and Abel Ferrara were considered before De Palma was hired. De Palma was originally reluctant to accept the job because he did not want to make another film about a Latino gangster as he did in Scarface (1983). But the script convinced him otherwise.
Pacino first met Judge ‘Edwin Torres’ in 1973 while he was preparing for Serpico (1973). At the time, Torres was in the midst of writing the novels on which the film is based and discussed them with Pacino. Twenty years later, Torres took Pacino to East Harlem to help him prepare of the role of Carlito.
In 1989, film producer Elliott Kastner filed a lawsuit against Pacino for allegedly backing out of a deal to star in a film as Carlito with Marlon Brando as Kleinfeld. The suit was eventually dropped.
According to John Leguizamo in his autobiography, he and Penelope Ann Miller did not get along during filming. He claims he got revenge on her by having the wardrobe department take in her clothes an inch at a time causing Miller to go on a crash diet.
Michelle Johnson screen tested for the role of Gail.
A traditional Jewish mezuzah can be seen in the background of Kleinfeld’s office: a small, thin bar affixed to the doorpost turned diagonally facing the entrance.