Although they play buddies in the film, Bruce Willis and Damon Wayans hated working with each other.
Assistant director James W. Skotchdopole later recalled how some of the production problems were caused due to the "Overabundance of alpha males on that project". As he said in an interview; "Bruce was at the height of his stardom, so was Joel, so was Tony and so was Shane. There were a lot of people who had a lot of opinions about what to do. There were some heated, early-Nineties, testosterone charged personalities on the line. It was a 'charged environment', shall we say."
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 Silver and he made sure for him to look and act just like Silver did.
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."
Composer Michael Kamen hated the film when he first saw it. The only reason he provided the score was out of his personal friendships with Bruce Willis and producer Joel Silver.
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.
With this film, Shane Black became the first writer to sell a spec script for one million dollars. According to Time magazine, he was originally offered 2.25 million dollars by Carolco Pictures, but decided to go with Warner Brothers for the lower (but record-setting) bid of 1.75 million dollars, 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 three million dollars.
Shane Black's original script was very different from the final film. It had more darker tone with more violence, and almost the entire second half of the script was completely different. Besides many differences with the plot and characters, Black's script also included more focus on the two main villains Milo and Shelly Marcone. Milo, for example, was an even nastier villain than he is in the film. In the script, besides being a hit man for Marcone, he also had a job as director of snuff films in which his men would kill kidnapped women in very violent ways. There was also a scene in the script where he brutally kills an entire family who accidentally showed up near the place where a meeting between his and Baynard's men took place. Other parts that were changed include: a big boat chase scene with Joe and Jimmy trying to escape from Milo and his men chasing them through the fog until their boat and helicopter crash into each other, a shootout and fight scene between Joe and Marcone's men in Joe's house, another shootout in Marcone's mansion in which Joe sneaks in after killing several guards, Joe and Jimmy saving Joe's wife Sarah from being killed with a chainsaw in one of Milo's snuff films, and different final showdown between Joe and Milo which took place outside Joe' office and after he chases and tries to shoot Joe while on foot, Milo gets killed by Sarah who shoots him with Joe's gun.
Joe Eszterhas was so incensed by news that the film's script sale dethroned his rank as highest paid screenwriter in Hollywood that he committed himself to reclaim his mantle with a new work. The resulting work, which paid him $3 million, nearly doubling Shane Black's $1.75 million sale for The Last Boy Scout, was Basic Instinct (1992).
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, this is why Silver was not involved in producing further Die Hard films.
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 in his house. Louis Baynard was also a villain in the script, and in the end, both he and his father die.
The movie that Darian is watching on television, 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 thieves in Die Hard (1988), also starring Bruce Willis and also produced by Joel Silver. Mel Gibson was offered the role of John McClane in Die Hard (1988), and Bruce Willis was offered the role of Martin Riggs in Lethal Weapon (1987).
Shane Black and Tony Scott both said in later years how the original script was far better than the final film.
Billy Cole's last words "Ain't life a bitch?", before committing suicide, were originally "I'm going to Disneyland.", a common phrase among Super Bowl winners.
Shane Black wrote the script after having taken a two-year break from writing, triggered in part by the end of a relationship.
Due to the behind-the-scenes arguments, and production problems, Warner Bros. brought in 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; different shot/angle for a dialogue scene between Joe and Jimmy in the car when they are driving toward Joe's house, an alternate shot/angle for another dialogue scene during the car chase where both of them and Darian are running from Milo and his henchmen, and shot of deleted sex scene between Jimmy and Cory.
The paraphrased-line of "There are no more heroes in the world" is also used in Lethal Weapon (1987) - both movies are written by Shane Black.
Joe Hallenbeck is physically assaulted twelve times throughout the movie. Seven times hit in the face. Three times hit on the back of the head. Once tasered, and once stabbed.
Damon Wayans trained with Los Angeles Raiders quarterback, Vince Evans, in preparation for his role as a former NFL quarterback
According to reports from members of test audience who saw earliest workprint version (possibly before it was re-edited by editor Stuart Baird on the orders by producer Joel Silver and Warner Bros.), it had different (temporary) music score and extended violent scenes (these scenes had to be cut down after the movie originally rated NC-17). The 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.
Marty Stratton and Hugo Martin, creators of Doom (2016), have largely credited Shane Black's script with inspiring the self-aware humor and style of the game's narrative.
The card that Darian gives Jimmie to autograph was produced by Pro Set, a trading card company based in Dallas, Texas. The card is fictitious, 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. Super Bowl Supermen, the headline of the card, was a legitimate part of the set.
Danielle Harris, who played Bruce Willis' daughter, said in a 2018 interview that this is still one of her favorites roles.
In the opening credits sequence, footage is taken from the 1990 Holiday Bowl (Texas A&M vs. BYU) and the final game in the movie itself.
Joe (Bruce Willis) mentions "reindeer goat cheese pizza", which Willis also mentioned in Hudson Hawk (1991).
A scene from Lethal Weapon (1987) is playing on television. Damon Wayans would later play Roger Murtaugh on the television series Lethal Weapon (2016).
The football scene at the end of the movie was filmed during the 1990 holiday bowl between the BYU Cougars and Texas A&M Aggies.
Joel Silver said in a Q&A for The Nice Guys (2016) that Shane Black's original title was "Die Hard". Silver asked if he could take the title for a project he was working on at the time called "Nothing Lasts Forever", which eventually became Die Hard (1988).
Taylor Negron described Joel Silver as extremely hands on and involved himself in every aspect of the production
Tony Scott wanted Grace Jones to play the small part of Cory, but the producers opposed the idea and Halle Berry was cast instead.
The line "Your show, ace" was also used in The Monster Squad (1987), which was co-written by Shane Black.
In the opening football scene, the names on two of the football players' jerseys are "Josephson" and "Coates." Barry Josephson produced the movie and Kim Coates plays "Chet" in the movie.
Number of times a character is struck by another character: 31 (nine being applied to Joe Hallenbeck).
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. The other was The Fan (1996).
Kim Coates' character is killed by Bruce Willis. Willis would end up killing Coates' character again in Hostage (2005).
Joel Silver would cast Halle Berry yet again five years later in 'Executive Decision' (1996).
Released in U.S. theaters the day before the one-year anniversary of the day that Look Who's Talking Too (1990) was released in U.S. theaters. This film also starred Bruce Willis and Damon Wayans as buddies, although they simply provided the voices of two characters.
Joe Hallenback makes two references to being "old". He says to Jimmy Dix, "you don't think a guy like me can beat you" and at the discussion about the $650 he says, "I am very old". Bruce Willis is only 5 years older than Damon Wayans
Right after Joe Hallenbeck (Bruce Willis) kicks Jimmy Dix (Damon Wayans) out of his house, Jimmy talks to Joe's Daughter, Darian (Danielle Harris) and signs his autograph. Jimmy has an Arizona state flag on the sleeve of his jacket.
Joe Hallenbeck's office was filmed only 350 feet (170 meters) from the house in Charmed (1998). See filming locations.
Cory says to Jimmy that if she were a cat, she'd purr. Halle Berry later starred in Catwoman (2004).
A shot from the ending of The Last Boy Scout (1991) stood in as a shot from Die Hard (1988) in S2E4 of the TV series Love (2016-2018)
Damon Wayans' character in the end jokingly quips Arnold Schwarzenegger's trademark line, "I'll be back!" Willis will later go on to co-star with Arnold in "The Expendables". Bruce Willis' character also mentions hitting an opponent in the face with a surfboard. This was the same slapstick death in 'Lethal Weapon 2' (1989).
Bruce Willis, star of The Last Boy Scout (1991), also went on to star in Striking Distance (1993), which was set in Pittsburgh. This is also the birthplace of The Last Boy Scout writer Shane Black.
Bruce Willis will again play a lead character named "Joe." As retired soldier Joe Colton in 'G.I. Joe: The Rise of Cobra' (2009).
The Last Boy Scout (1991) writer Shane Black acted in a short called The Boy Scout (2002). So a variation in terms of titles, as "Last" is missing from the latter.
Bruce Willis and Halle Berry would later appear together, sixteen years later in Perfect Stranger (2007).