Several incidents in the film are based on actual testimony given by captured mobsters. The meeting in the restaurant with the Italian mobster and the dead man's hand sequences are based on the recollections of various New York gangs.
Director Phil Joanou introduced his then-girlfriend Uma Thurman to actor Gary Oldman on the set, and she became Oldman's second wife shortly after the film premiered. The marriage only lasted 18 months before Uma filed for divorce in March 1992.
The scene where Jackie introduces his girlfriend to Terry, music by the band 'U2' can be heard playing in the background. Director Phil Joanou previously directed their live concert film U2: Rattle and Hum (1988) and, later, their music video for the single "One."
Another actor was originally cast in the part eventually played by Ed Harris. Harris had trouble accepting the role because he was still recovering from the injuries he suffered on the set of The Abyss (1989).