Was originally supposed to be directed by Martin Scorsese. Rocco Klein would have been the main character, played by Robert De Niro. Scorsese changed his mind, opting instead to direct Casino (1995), and De Niro went with him. Scorsese then asked Spike Lee if he wanted to direct. Lee accepted (and decided that Strike, not Rocco, would be the primary character), and Scorsese was given an executive producer credit.
The film's poster, designed by Art Sims, is an homage to the poster for Anatomy of a Murder (1959) which was designed by Saul Bass. Bass was not pleased with the poster and stated in an interview "when anyone steals something, they call it an 'homage'".
Spike Lee's previous film, Crooklyn (1994), featured the song "Crooklyn" over the end credits. This film features a remix of the same song during the opening scene in the courtyard. While the original version of the song was nostalgic and wistful, matching the tone of Crooklyn (1994), the version featured here is grim and pessimistic, in keeping with the mood of this film.