Shane Black’s career has had a fascinating, meteoric rise and fall (and rise again). The screenwriter hit the big time when his breakthrough screenplay for Lethal Weapon (1987) sold for $250,000. This kick-started a wildly popular action film franchise. He soon hit rock bottom with the heavily re-written (by others) modest hit, The Long Kiss Goodnight (1996), the script of his that sold for a staggering $4 million. And yet, even his weaker efforts still contain decent action sequences and playful banter between characters. What seemed to be missing in Black’s later films was depth and characterization – elements that made his screenplays distinctive. Perhaps this was as a result of meddling and script revisions at the hands of others. For Black, screenwriting came easy: “The fact that there were so few rules associated with it, so few actual structural maxims … you can just do what you want. So I played around and it was fun. I would just type to keep myself entertained. It turned out people liked that. They felt it represented an interesting way to go, but for me it was truly just typing to keep myself entertained.”

Studio executives were only interested in using Black to write formulaic drivel. Determined to make it, he wrote Lethal Weapon. The script was a blast of fresh air and ended up being made into a big budget action film starring Mel Gibson and Danny Glover. This kind of thing almost never happens in Hollywood and it’s a testimony to Black’s skill as a screenwriter that he achieved this kind of success so early on in his career. Lethal Weapon grossed over a $100 million. In the best tradition of Hollywood, money talks and so in 1990, Black was paid $1.75 million (an unheard of amount at the time) for The Last Boy Scout script. The next year it was made into a 1991 action movie starring Bruce Willis and Damon Wayans and directed by the late Tony Scott.

The film starts off literally with a bang as a pro-football player (a pre-infomerical Billy Blanks) pulls out a handgun right in the middle of a play and shoots three opposing players in his way to getting a touchdown before killing himself. Joe Hallenbeck (Bruce Willis) is a private detective hired by his best friend (Bruce McGill) to protect a stripper named Cory (Halle Berry in an early role). The best friend is subsequently blown up in a car and the stripper gunned down by thugs. Her washed-up, football-playing boyfriend Jimmy (Damon Wayans) hooks up with Joe to get some answers and some much needed payback.

“I had this period where I didn’t think I was any good at anything and fought desperately to stay afloat,” Black said in an interview with Creative Screenwriting magazine. And with that feeling in mind, Black wrote a movie that pushes the world-weary detective stereotype to then new, surreal levels. Willis’ performance and Black’s screenplay combine to produce a portrait of a guy who is so down and out that our first glimpse is a shot of him passed out in his own car while being harassed by snotty neighborhood kids with a dead squirrel. When we meet Joe he has a pretty simple outlook on life – a mantra, if you will, to start each day: “Nobody likes you. Everybody hates you. You’re gonna lose. Smile you fuck.” Willis, who has made a career out of playing world-weary tough guys, nails the defeated vibe that sticks to Joe like stink on dog poop. Joe’s actually a very disillusioned good guy, an ex-Secret Service agent who saved the President’s life once but got fired after he punched out a senator (Chelcie Ross) with a kinky streak. Throughout the movie, Willis delivers deadpanned one-liners while constantly getting the crap kicked out him. As a result, you can’t help but root for him as he and Wayans send the baddies to their well-deserved violent deaths.

Willis plays a classic burn-out, sporting the traditional slovenly appearance of a down-on-his-luck P.I. complete with unshaven look and rumpled clothes that he slept in. And that’s the best he looks, from that point on it’s all downhill as his face takes on cuts and lacerations accrued from fighting numerous bad guys. Joe actually uses his disheveled appearance to his advantage, like when a random baddie takes him into an alleyway to kill him. Joe buys time by cracking jokes about the flunkie’s wife and then, when the guy lets his guard down, stabs him in the throat with a broken bottle. The guy gurgles, “You bastard,” to which Joe curtly replies, “And then some.” Willis was born to spout Black’s dialogue. He’s the master of sarcastic comebacks and gets some real doozies in The Last Boy Scout. At one point, Jimmy chides him, “You read much?” Joe replies, “My subscription to Juggs magazine just ran out.”

Jimmy is also at an emotional cul-de-sac of sorts – popping pills to stave off chronic pain from football injuries he picked up as a player. Like Joe, he’s been disgraced from his former profession, kicked out of the league for gambling. He now spends time feeling sorry for himself by cultivating a drinking problem and nailing anything in a skirt despite having a super-hot stripper girlfriend played by Halle Berry (only in the movies!). Like Martin Riggs in Lethal Weapon, Jimmy lost his family to tragedy and it taints his entire worldview. Life means nothing and solving his girlfriend’s murder is the only thing he has left. Wayans shows that he’s more than just a goofy funnyman in a scene where he tells Joe how he got kicked out of football. It is an angry tirade tinged with hurt and bitter resentment as he was basically chewed up and spit out by an uncaring organization. His speech touches upon the harsh realities of professional sports.

Scott populates his movie with a fine collection of character actors, chief among them Noble Willingham as uber rich football team owner Sheldon Marcone and stand-up comedian Taylor Negron cast wonderfully against type as one of Black’s trademark polite, well-spoken sociopaths (see also Lethal Weapon’s Mr. Joshua and The Long Kiss Goodnight’s Timothy). Marcone is also a repeating motif in Black’s scripts. He’s an old, privileged white man who is greedy and corrupt. Think of the money-laundering retired general in Lethal Weapon and the war-mongering CIA boss in The Long Kiss Goodnight. Black clearly sees these men as the source of real evil in the world, pulling the strings that will result in death and destruction in the name of money. In all three films, the protagonists face insurmountable odds to do what is right regardless of the danger or risk to their own well-being.

Like most buddy action movies, the relationship between Joe and Jimmy starts off with plenty of friction as the quarterback resents the private investigator watching over his girlfriend because that’s his job. They trade a few insults and then decide to team up when she’s killed. Black has fun playing around with the dynamic between two guys who basically hate each other but are thrown together due to extraordinary circumstances. At one point, Jimmy cracks a joke to lighten the mood between them only to be rebuffed by Joe. Jimmy tells him, “I’m just trying to break the ice,” to which Joe replies, “I like ice. Leave it the fuck alone.” There are all kinds of snappy banter between them as Wayans tones down his trademark goofy shtick and more or less plays straight man to Willis’ deadpan humor.

Unlike a lot of buddy action movies, Black allows for the occasional lull, like the moment where Jimmy looks at a photograph of him and Cory and you can see on his face how upset he is by her death now that he has a moment to reflect on it. No words are said, Wayans’ face says it all. Joe and Jimmy represent the last bastion of decency in a world that is corrupt and morally bankrupt, where best friends double cross each other, wealthy businessmen are blackmailed, and wives cheat on their husbands. The deeper our two heroes go into investigating Cory’s murder the more corruption they uncover.

The aforementioned alleyway sequence and Cory’s death are vintage Tony Scott moments with his trademark look: smoke, neon and rainy streets at night. Think of it as the director’s version of a neo-noir. He is equally adept at action sequences as he is with showdown set pieces, like the scene where a henchman repeatedly offers Joe a cigarette only to punch it out of his mouth. Joe has been captured and is unarmed and outnumbered but he still has the balls to threaten to kill the guy if he hits him one more time. There is palpable tension as we wait for Joe to follow through on his threat (or be killed), which he does with brutal swiftness. It is reminiscent of the famous showdown between Christopher Walken and Dennis Hopper in True Romance (1993) where a tense scene could erupt in violence at any moment.

Successful screenwriter Shane Black made headlines in 1989 when he sold his spec screenplay (written without a contract from a studio or a producer) for The Last Boy Scout to the David Geffen Co. for an unprecedented $1.75 million. He had wisely taken advantage of the boom of independent production companies that sprouted up in the late 1980s looking for big budget action scripts. It must’ve come as validation of his abilities after what he had been through.

After his meteoric rise with the success of the script he had written for Lethal Weapon, a sequel was inevitable. The studio gave Black first crack at it. Something had happened to the writer after enjoying a taste of notoriety and his first draft was even darker than what he had written for the first movie. For starters, he proceeded to kill off Mel Gibson’s character. Not surprisingly, the studio didn’t want to go that route and Black quit the project. Then, he lost the desire to write. A family illness coupled with the break-up of a long-term relationship rocked his already shaky confidence. For the next two years he did no writing and instead lived in fear of the next project and failing. Out of this dark period in his life came the script for The Last Boy Scout, which he wrote in five months.

For the script, Black drew on such influences as hard-boiled crime fiction by the likes of Raymond Chandler and Ross McDonald because they wrote about “personal integrity, morality, conflict, dealing with insanity, dealing with pain and death.” He wanted to write a modern private investigator story set in Los Angeles. He decided to set his story with the sleazy side of professional football as the backdrop because it matched up well with his take on a Chandleresque private investigator story. For Black, football “combines the spirit of the American hero with the spirit of American greed.” After finishing the script, he didn’t think it would sell because “it was weird” and “too rough for most people. It’s not a commercial formula; it’s a very raunchy, down and dirty detective film.”

Originally, director Tony Scott had a war movie taking place in Afghanistan set up as his follow-up to the Tom Cruise racing car movie Days of Thunder (1990). However, the script didn’t come together and he was given The Last Boy Scout. He liked it so much that he agreed to do it. Not much has come out of what went down during filming but what little has suggests a contentious shoot. With titanic egos like producer Joel Silver, movie star Bruce Willis and Tony Scott, they were bound to clash and they did as Scott later admitted, “I got caught a little bit between Bruce and Joel Silver … I was pushed in terms of the cast and in terms of how I was shooting it.” He also felt that Black’s script “was better than the final movie.” Of the experience, all Silver would say was that it was “one of the three worst experiences in my life.”

The Last Boy Scout performed fairly well at the box office and has since enjoyed a second life on video and television (thank you, TBS). Black went on to get paid more than $1 million for his rewrites on The Last Action Hero (1993), a criminally underrated romp that is the granddaddy of self-reflexive action movies. This movie was crucified by critics and did not perform as well at the box office as expected but this did not tarnish Black’s reputation either. However, he disappeared from movies for a few years before coming back with a vengeance with the quirky private detective movie Kiss Kiss Bang Bang (2005) and Iron Man 3 (2013). The Last Boy Scout is a lean, mean guilty pleasure with a misanthropic streak that is uncompromisingly un-PC in attitude. This is further reinforced by its rather poor view of women. They are either liars and cheats (Joe’s wife), whores (Cory), or foul-mouthed brats (Joe’s daughter). Joe takes it all grimly in stride because hey, he’s already hit rock bottom. He doesn’t care about anyone or anything, including himself. Action films don’t get any nastier than this one.