Just as is mentioned in the opening credits of Deadpool, the writers are the real heroes of filmmaking. But they rarely get the recognition they deserve, as all the praise generally goes to the director. However, in the late-'80s, that briefly changed, as writer Shane Black had an almost rock star-like status in Hollywood.
Black was the most sought-after writer for years, and he penned some of the best crime comedy screenplays of the '90s, and in the 2000s, he became one of the most exciting directors too. Unfortunately, a handful of his movies are sleeper hits that almost always underperform at the box office — but they also often become cult classics.
The Monster Squad (1987) - $3.7 Million
Available to rent on Amazon Prime Video.
The Monster Squad is the least like any of Black's other movies, and it's full of ideas that the writer never returned to, the most obvious being the horror genre. The film wasn't hated by critics, but it wasn't exactly beloved either, and due to being such a "meh" movie, it struggled to find an audience and bombed at the box office.
The movie is an outlier in Black's filmography and way before he established his style, making it the first failure in his career. Interestingly, The Monster Squad is a parody film, as is Last Action Hero, so for as great a writer as Black is, the parody genre might not be something he's cut out for.
Kiss Kiss Bang Bang (2005) - $15.7 Million
Available to rent on Apple iTunes or Amazon Prime Video.
Being more of a writer than a director, it wasn't until 2005 when Black made his directorial debut. Just like the movies that came before it, Kiss Kiss Bang Bang is yet another buddy cop movie, only this time the trope is flipped on its head. It follows a con artist-turned-actor (Robert Downey Jr.) being pulled into a criminal underworld when training under a private investigator.
The movie is one of the best crime comedies of the 21st century, but audiences didn't realize that when it was first released 17 years ago. Kiss Kiss Bang Bang barely made back its budget and is considered a box office disaster. However, it has gotten a lot of attention in recent years after Robert Downey Jr.'s growing popularity from playing Iron Man in the MCU.
The Last Boy Scout (1991) - $59.5 Million
Available to stream on Netflix.
The Last Boy Scout again forces an unlikely pair to work together, as the film follows a former quarterback teaming up with a private investigator. It's the first of many Black-written movies that sees a professional of a random industry pair with a private eye, and it worked brilliantly in terms of the story.
However, despite being enormously entertaining and having a compelling mystery, it didn't quite make the numbers the studio expected it to. Even a starring role from Bruce Willis, who was one of the biggest movie stars in the world at the time, couldn't keep the film from underperforming.
The Nice Guys (2016) - $62.7 Million
Available to stream on Hulu.
The Nice Guys is the latest original movie to come from the mind of the crime comedy-loving writer-director. It is somewhat of a spiritual sequel to Kiss Kiss Bang Bang, as it again follows a couple of unlikely matched private detectives, and this time they're trying to solve the murder of a porn star and the film is set in the 1970s.
There's a lot more star power this time around, as Russell Crowe and Ryan Gosling are in the lead roles, and Gosling is currently one of Hollywood's most bankable actors. But while the movie did make a lot more than Kiss Kiss Bang Bang, The Nice Guys had a much bigger budget too. Even though it's one of the most rewatchable movies of the past decade, the 2016 film was another box office failure for Black.
The Long Kiss Goodnight (1997) - $89.4 Million
Available to rent on Apple iTunes or Amazon Prime Video.
The Long Kiss Goodnight follows another private investigator, only this time, he's paired alongside a school teacher with amnesia who is trying to figure out who she really is. The movie has become more popular in the years since its release, but compared to its budget, its $90 million box office intake isn't all that great.
The movie had an inflated budget of $65 million, which probably had something to do with Samuel L. Jackson's salary, as he was one of the most in-demand actors at the time. But even without considering the budget, the movie's worldwide gross was generally disappointing, and it could have had something to do with the confusing marketing.
Lethal Weapon (1987) - $120 Million
Available to stream on HBO Max.
Lethal Weapon is what turned Black into a Hollywood rockstar. At the time, everybody wanted a screenplay from Black, and it was all thanks to this 1987 movie. With the Lethal Weapon screenplay, Black did something that few other screenwriters do, which was to give the reader notes on camera angles and even make jokes in the action notes of the script, according to The Irish Times.
For example, when describing a Beverly Hills home in the screenplay, he writes, "The kind of house I'll buy if this movie is a huge hit." While that's generally considered amateurish and frowned upon by Hollywood execs, it worked out well for Black. And based on the movie making 10 times its budget, Black could probably afford a couple of those houses.
Last Action Hero (1993) - $137 Million
Available to stream on Netflix.
Last Action Hero is one of the more experimental screenplays from Black, as it incorporates fantasy elements and is much more of an explosive action movie than the crime films he's known for. However, it still has Black's signature tongue-in-cheek humor, but in a different kind of way. The movie is satirical of action tropes and cliches, and if that wasn't clear enough, it stars Arnold Schwarzenegger to hammer the message home.
Unfortunately, the fantasy elements and starring role from one of the biggest stars ever wasn't enough to sell viewers on the wild concept. The poor box office performance is partly because it's genuinely one of the worst John McTiernan-directed movies. But its opening weekend was also during Jurassic Park's second week in theatres, and that movie was breaking box office records.
The Predator (2018) - $160 Million
Available to rent on Apple iTunes or Amazon Prime Video.
The Predator is Black's most recent movie, which he both wrote and directed. 20th Century Fox's decision to hire Black for the movie makes perfect sense on paper, as both the director and the IP are synonymous with '80s action classics. Black was even an uncredited script doctor for the original movie back in 1987.
However, whether it was through studio meddling or a bad day at the office for Black, The Predator was yet another missed opportunity in the series. And while the massacre in the science lab is one of the best kills in the Predator franchise and worth the price of admission alone, that one scene couldn't keep the film from underperforming.
Iron Man 3 (2013) - $1.214 Billion
Available to stream on Disney+.
It's almost poetic that Black took over from Jon Favreau to direct Iron Man 3. According to Decider, Downey's performance in Kiss Kiss Bang Bang is what made Favreau want to cast the actor as Tony Stark in the first place.
While Iron Man 3 is a fine Iron Man movie, it's a great Black movie, and though some don't like the Mandarin twist, it's classic Black humor. And considering that the 2013 movie is a love-it-or-hate-it film amongst MCU fans, it made an impressively huge number at the worldwide box office. The explanation behind it might be because it was coming right off the heels of The Avengers, but it's still an impressive feat.