Final collaboration between producer Joel Silver and actor Bruce Willis. The making of this film, as well as Die Hard 2 (1990) and Hudson Hawk (1991), took a toll on their professional relationship. Coupled with Silver's ousting from Fox due to production delays and budget overruns on Die Hard 2, Silver was no longer involved in further Die Hard films.
Tony Scott hated working with producer Joel Silver so much that he based the character Lee Donowitz (Saul Rubinek), movie producer and cocaine user and dealer in his next movie True Romance (1993) on Silver and he made sure for him to look and act just like Silver did.
A riot nearly occurred during filming at the Los Angeles Coliseum. Hundreds of extras were recalled for a second day of shooting, but a last minute decision was made to cancel the recall. The extras were not informed of the decision and arrived expecting a day of work. They were refused pay by the production, and as discontent grew, they began to surge against the barrier that surrounded the set. Riot police were called in to disperse the crowd.
In a New Yorker profile, Joel Silver said that the making of this film was "one of the three worst experiences of his life." Tony Scott also spoke about how miserable production was, largely because Silver and Bruce Willis took over the production, altered parts of Shane Black's script, and made him shoot scenes he hated under threat of being fired and having to forfeit his salary.
The conversation between Joe and Jimmy about the 650 dollar pants was taken from a deleted scene in Lethal Weapon (1987). Murtaugh's daughter is wearing an expensive dress for a New Year's Eve party and he asks, "It doesn't have a little television in it?" She says, "No", and Murtaugh mutters, "I am very old."