Trivia / Carlito's Way

  • Actor-Inspired Element/Dyeing for Your Art: It was Sean Penn's idea to shave a receding hairline into Kleinfeld's head.
  • Harpo Does Something Funny: John Leguizamo improvised many of his lines. He actually turned down the role four times and only accepted when he was allowed to ad-lib.
  • Hostility on the Set: John Leguizamo revealed in his autobiography that 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.
  • Money, Dear Boy: 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.
  • Production Posse: Brian De Palma reused several actors from Scarface (1983): Al Pacino, Al Israel, Ángel Salazar, Jorge Porcel, Michael P. Moran, and Caesar Cordova.
  • Romance on the Set: Al Pacino and Penelope Ann Miller became romantically involved during filming. Miller spoke publicly about their romance in interviews. But Pacino was in a relationship with Lyndall Hobbs at the time. Pacino attended the film's premiere with Hobbs and avoided Miller entirely.
  • Wag the Director: According to Brian De Palma, Sean Penn demanded 30 takes of the shot of Kleinfeld asking Carlito to help him with Tony T's escape. When De Palma wanted to move on to the next shot, Penn screamed at De Palma. He continued to yell at De Palma on the ride back to New York City. He later called De Palma on the phone to continue yelling at him. De Palma said that was the only argument they had on the film.
  • What Could Have Been:
    • Charlie Sheen was considered for David Kleinfeld. At an early stage, Marlon Brando was to play the role.
    • 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 also featured a scene at a railway station.)
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