For many, Shane Black is best known as the writer of classic 1980s and ’90s action movies like Lethal Weapon, The Last Boy Scout, Last Action Hero, and The Long Kiss Goodnight. As legendary as his screenwriting credits are, though, Black has built an almost equally impressive second career for himself over the past 20 years as a director. He has made two of the most beloved crime comedies of the 21st century. On top of that, he’s directed two franchise sequels that, whether you like them or not, manage to subvert your expectations at nearly every turn.
Black, unfortunately, hasn’t gotten to direct as many movies as his fans would like, and it’s been six years since his last film. Nonetheless, his directorial efforts are all noteworthy enough to warrant being discussed in the internet’s preferred manner, which is to say ranked from worst to best.
4. The Predator (2018)
Fans’ hopes initially skyrocketed when it was announced that Shane Black would be directing The Predator. Black, after all, has had a close connection to the Predator franchise since he starred in 1987’s Predator as Sergeant Rick Hawkins. Despite that fact, his 2018 entry in the franchise is easily the weakest film that Black has directed to date. The movie, which follows several soldiers trying to fend off a pair of Predators that unexpectedly come to Earth, is full of interesting ideas. Its attempts to bring the Predator series to the suburbs, in particular, allow Black to inject the film with some of his uniquely subversive creative spirit.
However, nothing ultimately comes together or works well enough in The Predator to become the kind of memorable blockbuster that many hoped it would be. It’s the least distinct movie that Black has ever made, and while it does contain the same slightly brutal edge present in many of his films, it’s largely devoid of his trademark cleverness. Watching The Predator, it’s easy to admire Black’s desire to reinvent such a beloved sci-fi franchise, but his attempts to do so repeatedly prove to be in vain across its 107-minute runtime.
3. Iron Man 3 (2013)
Iron Man 3 isn’t nearly as bad as many comic book readers would have you believe. Directed and co-written by Black, it was the first Marvel Cinematic Universe film to follow 2012’s The Avengers, which may have been why some fans were disappointed by it in 2013. Many went into the sequel wanting another straightforward superhero movie like The Avengers, Iron Man, and Iron Man 2. Instead, they got a twisty, scrappy dramedy that finds Tony Stark (Robert Downey Jr.) at his least charismatic following his near-death experience at the end of The Avengers. Traumatized and eager to embrace his most isolating, self-protective tendencies, Tony’s life is targeted by scorned figures from his past in Iron Man 3, and he very nearly loses everything that he holds dear.
The film is a psychologically darker sequel than many thought it would be. At the same time, it doesn’t take the comic book lore of its story at all seriously. That dichotomy has made it hard for many Marvel fans to accept Iron Man 3. To be fair, the film isn’t perfect, either, and several of its comic swings do fall disappointingly flat. Time has proven kind to Iron Man 3, though, and in a period where it feels like the MCU is only becoming more risk-averse and generic, the movie’s anarchic originality just seems to grow all the more refreshing and welcome.
2. Kiss Kiss Bang Bang (2005)
Since it was released in theaters and made little-to-no impact at the box office, Kiss Kiss Bang Bang has been viewed as an underseen gem, and for good reason. The 2005 neo-noir crime comedy marked Shane Black’s directorial debut, and it also united him for the first time with Robert Downey Jr. The actor leads the film as a smart-mouthed New York thief who ends up embroiled in a Los Angeles-based crime conspiracy alongside his childhood crush (Michelle Monaghan) and an acid-tongued private investigator (Val Kilmer). Behind the camera, Black sets almost all of his lead trio’s pulpy misadventures against the backdrop of a Los Angeles that is less sunny and far darker than its reputation would lead anyone to believe.
The film’s script packs in more witty one-liners, shockingly bloody twists, and moments of screwball banter than viewers may know what to do with the first time they watch. The movie is, in other words, pure Shane Black. It’s endearingly messy, endlessly clever, and overwhelmingly charismatic. Neither Kilmer, Downey Jr., nor Michelle Monaghan has ever been quite as charmingly zany as they are in Kiss Kiss Bang Bang, which is even more tongue-in-cheek, explosive, entertaining, and impactful than its title suggests. If you’re one of the many that haven’t seen it yet, then consider yourself lucky. You’re in for quite the ride.
1. The Nice Guys (2016)
Like Kiss Kiss Bang Bang, 2016’s The Nice Guys received way less attention than it deserved when it originally hit theaters. Based on how many viewers were surprised by Ryan Gosling’s comedic abilities in Barbie last year, it seems like the film is still flying farther under the radar than it should, too. Make no mistake about it: Gosling is startlingly hilarious in Barbie, but anyone familiar with The Nice Guys has been long aware of just how funny the actor can be onscreen. He stars in the film as a sad-sack P.I. who teams up with a hard-knuckled enforcer (Russell Crowe) to investigate the disappearance of a government official’s daughter in late 1970s Los Angeles.
Before long, the two have discovered that the crime that brought them together is related to not only the mysterious death of a famous porn star but also a conspiracy that spreads wider than they ever could have imagined. The film’s plot feels like it could have been ripped right out of the pages of a paperback potboiler, but as delightfully convoluted as its central mystery turns out to be, it’s ultimately Black’s razor-sharp writing and Gosling and Crowe’s central performances that elevate The Nice Guys to incredible heights. The film is overflowing with unforgettable comedic gags, including a failed break-in attempt on the part of Gosling’s Holland March and an underwater encounter with the ghost of Richard Nixon that’ll leave you laughing long after it’s ended.
The Nice Guys is Black at the peak of his powers. It’s the funniest and most watchable film of his entire career. For as many injustices as there are scattered throughout its plot, the greatest crime of all when it comes to The Nice Guys may also be that we’ll likely never get to see Black, Gosling, and Crowe reunite for the sequel that we — and they — deserve.
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