One of the reasons why Sir Michael Caine agreed to appear in this remake to one of his best movies as it afforded him the chance to work with his friend, Sylvester Stallone. The two had bonded when they made John Huston's À nous la victoire (1981).
Franchise Pictures was reluctant to cast Mickey Rourke, in light of his troubled past as a Hollywood bad boy. Friend Sylvester Stallone, who put Rourke up for the role, guaranteed a portion of his salary, so if Rourke did cause any delays or problems, the production would be covered. Rourke turned up every day on time, and was a complete professional. His work impressed Franchise enough that they hired him shortly after for their next movie, The Pledge (2001).
The original screenplay, on which Sylvester Stallone signed, was much more violent, and focused more on the "revenge" element. The book is even more severe.
For the flashback scenes that show Richie's murder, Stephen Kay wanted the film to look grainy and damaged, so he asked Deluxe, the film processor, to think outside the box. Happy to oblige, the techs at Deluxe tied the film to the back of a car and drove it around their parking lot, creating the scratched look. The experiment was short-lived when a Deluxe executive saw it, and ordered them to stop, fearing it would give the company a bad name.
Sir Michael Caine, who plays Cliff Brumby in this movie, played Jack Carter in La loi du milieu (1971).