Trivia / Carlito's Way

  • 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.
  • 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.
  • Throw It In: John Leguizamo improvised many of his lines.
  • 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.
    • 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.)