During halftime at a televised football game, L.A. Stallions running back Billy Cole receives a phone call from a mysterious man named Milo, warning him to win the game or he's "history". Cole ingests PCP and, in a drug-induced rage, brings a gun onto the field, shooting three opposing players to reach the end zone. Cole then shoots himself in the head. Meanwhile, private investigator Joseph Hallenbeck discovers that his wife Sarah is having an affair with his best friend, Mike Matthews. Mike gives Joe an assignment to act as bodyguard for a stripper named Cory. Afterwards, Mike is killed by a car bomb outside Joe's house.
Joe is approached by Cory's boyfriend, former Stallions quarterback Jimmy Dix, who was banned from the league on gambling charges and alleged drug abuse. After an argument where Joe and Jimmy scuffle, an annoyed Jimmy takes Cory from the stage while she is performing. Joe plans to wait outside, where he is knocked out by a team of hitmen. Jimmy and Cory leave the bar in separate cars while Joe is left to dispatch one of the hitmen. When Cory is struck from behind and stops to confront the other driver, she is killed by the hitmen. Jimmy is fired upon and pinned down, but is saved by Joe.
At Cory's house, Jimmy and Joe find a taped phone conversation between Senator Calvin Baynard, who is leading a congressional investigation into gambling in sports, and Stallions owner Shelly Marcone. When the tape is ruined in Joe's faulty car stereo, Jimmy realizes that Cory tried using the tape against Marcone to put Jimmy back on the team, prompting Marcone to send the hitmen. Joe saves Jimmy from a second car bomb, and manages to trick two hitmen into blowing themselves up. However, the explosion destroys the remaining evidence.
Joe reveals to Jimmy that when he was in the Secret Service, he witnessed Baynard torturing a woman in a hotel room and assaulted him to make him stop. Baynard retaliated by having Joe fired from the Secret Service for refusing to cover up the incident. At Joe's house, Jimmy meets Joe's abrasive daughter Darian. When Joe catches Jimmy attempting to use illegal painkillers in the bathroom, Joe kicks him out. As Jimmy leaves, Darian asks him to sign a football trading card, stating that Joe was a fan of Jimmy's and never watched another game after he was banned from the league. He leaves her with the signed card, "To the daughter of the last Boy Scout."
Upon learning of Mike's affair with Sarah, the police assume Joe killed him and move to arrest him. But Milo, Marcone's top henchman, captures Joe first and shoots an officer using Joe's gun. Marcone explains to Joe that he has been buying Senate votes to legalize sports gambling, but that Baynard tried to blackmail Marcone for $6 million. Being aware of Joe's history with Baynard, Marcone explains it would be cheaper to kill the senator and frame Joe for the murder. Joe is forced to hand a briefcase full of money to Baynard's bodyguards, who switched it with a wired briefcase. Joe is rescued by Jimmy and Darian, and acquires both briefcases after running the bodyguards and Milo off the road. However, Milo survives and kidnaps Darian after Joe leaves her to wait for the police.
Heading to the stadium to save Darian, they are caught and brought to Marcone's office. Jimmy creates a diversion, allowing them to fight their way free. Knowing Milo will attempt to shoot Baynard, Joe goes after Milo while sending Jimmy to warn the senator. Grabbing the game ball, Jimmy throws it at Baynard, knocking him down just as Milo starts shooting. Joe knocks Milo to the edge of the stadium light platform, where police shoot him several times. The suitcase of money is recovered and the fleeing Marcone, having escaped with the rigged briefcase, is killed when he opens it at his house. The next day, Joe and Sarah reconcile, and Joe and Jimmy decide to become partners.
The film was based on an original script by Shane Black who was known for writing Lethal Weapon. He wrote the script after having taken a two-year break from writing, triggered in part by the end of a relationship. Black later recalled:
I was busy mourning my life and, in many ways, the loss of my first real love. I didn’t feel much like doing anything except smoking cigarettes and reading paperbacks. All things come around. Time passed and eventually I sat down and transformed some of that bitterness into a character, the central focus of a private eye story which became The Last Boy Scout. Writing that script was a very cathartic experience, one of the best experiences I’ve ever had. I spent so much time alone working on that. Days which I wouldn’t speak. Three, four days where I maybe said a couple words. It was a wonderfully intense time where my focus was better than it’s ever been. And I was rewarded so handsomely ($1.75 million) for that script, if felt like a vindication and like I was back on track.
The Last Boy Scout was filmed in 90 days between March 11 and June 9, 1991.
The film had a very troubled production. Everybody involved in the film had a miserable time working on it. Producer Joel Silver and main actor Bruce Willis took over the production, altered much of Shane Black's original script and forced director Tony Scott to film scenes he disliked under threat of being fired. Silver mentioned in later interviews how making of The Last Boy Scout was one of the three worst experiences in his life, while Willis swore that he would never work with Silver again. In his next film, True Romance, Scott parodied Silver by having character Lee Donowitz, a movie producer who is also a cocaine user and dealer, act just like Silver.
Scott said about Silver; “He’s insane, with long, horrible fits of sanity.” He compared Silver to a fighter pilot riding as a passenger. “As soon as you hit a little bit of turbulence, he’s right away going to throw the guy out of the window and take over the steering.”
Taylor Negron, who played Milo described Silver as extremely hands on and involved himself in every aspect of the production.
Assistant director James 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.”
Writer Shane Black also said about problems with the script; “I was forced to do more rewriting on that movie than on anything else I’ve done. There was tremendous pressure from the studio to get Bruce Willis and have this be a follow-up to Die Hard. He was reluctant, and rightly so: ‘This whole movie is about me saving my wife. I just did that in Die Hard.’ So they said, ‘OK, let’s minimize the wife and, and while we’re at it, add a big finale. There was a general pressure to somehow make it bigger.”
Although they play buddies in the film, Willis and Damon Wayans hated working with each other so much that they despised each other.
Composer Michael Kamen hated the first cut of the film when he saw it, and he only agreed to compose music for it because of his personal ties to Willis and Silver.
Editor Stuart Baird was brought in by Silver and Warner Bros. to completely re-edit the film since the original cut turned out to be a borderline unwatchable workprint. Baird did the same job with several other Warner Bros. films, including Tango & Cash, which suffered even more problems during production.
One of the reasons for problems with post production re-editing of the film was Scott's habit of filming excessive coverage with multiple cameras. Editor Mark Helfrich said how he had to go through "mountains of raw material" in order to edit the first cut of the film. He mentioned; “There was more footage shot for The Last Boy Scout than on any film I had ever worked on.” He recalled with incredulity that the work of previous editors appeared to have been rejected, taken apart and put back into the daily reels: “There were still splices all over the place.” Expert action movie editor Mark Goldblatt who also worked on the film recalls it as one the most painful and frustrating experiences of his entire career and refuses to talk about it in interviews. He did mentioned in podcast interview how before he was brought in several other editors were hired but were then fired for some reasons, and how Warner Bros. started testing the movie before it was completely finished. They were very worried about the movie because they put lot of money into it but reactions from test screening audience weren't very positive, and they also thought that Willis's character wasn't very likeable. It wasn't until Stuart Baird was hired that movie was finally turned into something watchable. Some later cuts were done on the film's graphic scenes after it was originally rated NC-17, which explains quick-cut edits in some of the death scenes in the film.
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).
Shane Black and Tony Scott both said in later years how the original script was far better than the final film.
The film was nominated for two MTV Movie Awards.Best Action Sequence – For the helicopter blade sequence
Best On-Screen Duo – Bruce Willis & Damon Wayans
The film underperformed expectations given the star power and hype surrounding the then record price paid for the screenplay by Shane Black ($1.75 million).
Roger Ebert gave the film three stars, saying it was "a superb example of what it is: a glossy, skillful, cynical, smart, utterly corrupt and vilely misogynistic action thriller". It has a 44% approval rating on Rotten Tomatoes based on 34 reviews. Reviews were mixed, and some critics cited the Christmas time release for such a violent film as a reason for its somewhat underwhelming box office. It grossed $7,923,669 in its opening weekend, and the total gross was $59,509,925. Although the film was not a blockbuster, it helped Bruce Willis recover his star status after the disastrous Hudson Hawk, and both turned a profit at the box office and became hugely popular in the video rental market.
The film's score was composed and conducted by Michael Kamen (who also scored Hudson Hawk that year), his only work for Tony Scott. Bill Medley performed the song "Friday Night's A Great Night For Football," written by Steve Dorff and John Bettis, on screen during the opening credits (the song is also reprised over the end titles); the song was released as a CD single by Curb Records.
On August 25, 2015, La-La Land Records released a limited edition soundtrack album featuring most of Kamen's score, plus Medley's song.