In a New Yorker profile, producer Joel Silver said that the making of this film was "one of the three worst experiences of (his) life." Director 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 movie that Darian is watching on TV is Lethal Weapon (1987) which was also written by Shane Black and produced by Joel Silver. Specifically, she's watching the scene in which Mel Gibson is being tortured by Al Leong who was also one of the terrorists in Die Hard (1988), also starring Bruce Willis. Ironically Mel Gibson was offered the role of John McClane in Die Hard and Bruce Willis was offered the role of Martin Riggs in Lethal Weapon (1987) but they turned it down and it went to each other vice versa.
Tony Scott hated working with producer Joel Silver so much that he based the character Lee Donowitz, movie producer and cocaine user and dealer in his next movie True Romance (1993) on Joel Silver and he made sure for him to look and act just like Silver did.
With this film, Shane Black became the first writer to sell a spec script for $1 million. According to Time magazine, he was originally offered $2.25 million by Carolco Pictures, but decided to go with Warner Brothers for the lower (but record-setting) bid of $1.75 million so that he could work with Joel Silver, who had also produced his script for Lethal Weapon (1987). This record stood for 67 days until Carolco purchased a screenplay by Joe Eszterhas, which became Basic Instinct (1992), for $3 million.
In the original script, the entire third act was set on water. Also, Hallenbeck's grudge with senator Baynard was completely different from the movie. In the script, Hallenbeck was working security for the Baynard family when Louis Baynard, President Baynard's son, kills a mother and her child in a drunken car accident. When Hallenbeck refuses to cover for the president's son, they plant half a kilo of crack cocaine in his house. Louis Baynard was also a villain in the script, and in the end both he and his father die.
The conversation between Joe and Jimmy about the $650 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 TV in it?" She says, "no" and Murtaugh mutters, "I am very old."
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 an interview with Tony Scott, he mentions that a stray cat managed to get into Bruce Willis's trailer and started humping Bruce's hairpiece. The piece was mangled but they managed to get it looking wearable again.
Due to the all behind the scenes arguments and production problems, Warner Bros. brought in editor Stuart Baird to heavily re-edit the movie. For the same reasons, Baird also re-edited Tango & Cash (1989), another Warner Bros. movie which had even more problems during filming and post production. Some alternate scenes can be seen in the theatrical trailer; alternate angle for dialogue scene between Joe and Jimmy in car when they are driving towards Joe's house and alternate angle for other dialogue scene during the car chase where both of them and Darian are running from Milo and his henchmen.
The card that Darian gives Jimmie to autograph was produced by Pro Set, a trading card company based in Dallas,TX. The card is a fictitious one, but appears to be of similar design to a real set of cards made by Pro Set. In 1990, the company produced a Super Bowl commemorative set. Superbowl Supermen, the headline of the card, was a legit part of the set.
This wasn't the first time that Bruce Willis and Damon Wayans co-starred together. They "co-starred" the year before in Look Who's Talking Too (1990), voicing the thoughts of two toddlers. Willis voiced Mikey while Wayans voiced Eddie.
This is one of two films directed by Tony Scott with a sports theme, plus a white actor and a black actor who shared top billing. American football was the sports theme in this film, which starred Bruce Willis and Damon Wayans. In 1996 Scott directed The Fan, the sports theme was baseball, which starred Robert De Niro and Wesley Snipes.
According to reports from members of test audience who saw earliest workprint version of The Last Boy Scout (possibly before it was re-edited by editor Stuart Baird on the orders by producer Joel Silver and Warner Bros. studio), it had different (temporary) music score and extended violent scenes (these scenes had to be cut down after the movie originally rated NC-17). Biggest difference between workprint and theatrical version was the opening song, which in the workprint was "Are You Ready For Some Football Tonight" by Hank Williams Jr, while in the theatrical version song "Friday Night's A Great Time For Football" by Bill Medley was used.