Kiss Kiss, Bang Bang (2005)

In the mid-90s, Shane Black was the highest paid screenwriter in Hollywood.

After creating the buddy cop genre with Lethal Weapon, Black rode a dizzying lightspeed tightrope by writing a string of high profile hits that stuck close to well-loved Hollywood tropes while skewering the conventions of action filmmaking, traditional masculinity and gender roles, and movie stardom.

But then, in 1996, The Long Kiss Goodnight happened. Long Kiss is, on paper, the next step in Black's recontextualizing of Hollywood genre tropes: an action/noir/spy flick starring a woman and a black man in roles traditionally reserved for white men which is literally about a woman reclaiming her identity. It starred Geena Davis and Samuel L Jackson, two stars with plenty of action credits to their name, though Davis and director Renny Harlin were still stinging from the disastrous failure of Cutthroat Island, a one-two punch that neither ever recovered from.

Black has said that the studios begged him to make the lead male: "It might have made more money, they told me," He said, "but it had to be a woman. The lead had to be female."

When Long Kiss became one of the biggest bombs of all time, Black went underground to lick his wounds, and prepare for a comeback.

And speaking of comebacks. Robert Downey Jr. is perhaps the face of the Hollywood redemption story. Born into a house as rampant with celebrity as with drug abuse, Downey Jr.'s looks, his father's access to the Hollywood elite, and nuclear fission-level charisma made him one of the biggest stars of the 80s even as his catastrophic struggle with drugs and alcohol ensured his career was built on tindersticks. 

Starting, tidily enough for our purposes, in 1996, Downey Jr. was arrested multiple times for drug-related reasons. He blamed his addiction on his father's lifestyle, and told a judge in 1999 "It's like I have a shotgun in my mouth, and I've got my finger on the trigger, and I like the taste of the gun metal."

Downey spent a year in prison and was released in 2000. Within a year, he had been cast in Ally McBeal, revived the show's ratings, won a Golden Globe and was then arrested again, fired from the show, and went back to rehab. It seemed like his comeback had happened, and failed.

Val Kilmer's story is less dramatic, but still classic Hollywood: after a string of unbelievable hits as iconic characters in the 90s: Batman, Jim Morrison, Heat's icy bank robber Chris, due to reports he was difficult to work with, Kilmer faded out of the spotlight.

So, then, Kiss Kiss, Bang Bang, a story about how Hollywood fucking sucks by a bunch of guys that went through the ringer for Hollywood.

For Black, making his directorial debut, it's familiar territory: a neo noir comedy that splits the hard-boiled private eye protagonist in two. Downey Jr plays Harry, a bad thief who blunders through life, and Kilmer plays "Gay" Perry, a bonded PI who hates his job hiding in bushes taking snapshots of cheating husbands, and whose homosexuality is a deliberate inversion of the aggressive heterosexuality of traditional noir PIs. (Whether Black's characteristic lack of subtlety manifests in a portrayal of Perry that is more homophobic than subversive is up for debate.)

Kilmer's deadpan, played so effectively as a leading man in Heat and The Salton Sea, is hilarious and a true revelation for anyone not familiar with his breakout role in Top Secret! Perry is no effiminate stereotype: he is competent but jaded, and Black takes advantage of Kilmer's aging visage to show us a man who is perpetually so fucking tired. 

Adding to the subversion is Michelle Monaghan in her first lead role, and she brings the same laconic charm and grounded emotional accessibility that would serve her so well two years later, in the equally subversive (but way less fun) Gone, Baby, Gone and a decade later in True Detective. Monaghan easily keeps pace with Kilmer and Downey, and the three of them are a screwball bulldozer. This movie's charm could solve the energy crisis.

And then there's RDJ. After thoroughly committing to cleaning up his act, Kiss Kiss was the launchpad for a fucking ridiculous rocketship back to the A-list: in less than five years, he made this, The Singing Detective, fucking Zodiac, Sherlock Holmes, Tropic Thunder, and a little indie gem called Iron Man which I haven't seen but I guess is about a robot?

In Kiss Kiss, Bang Bang, Downey isn't just fast, he isn't just charming, he isn't just a loveable pain-in-the-ass: he delivers one of the most effortlessly watchable performances in film acting history. Even without knowing his personal struggles he is electric, but when you do know what he's been through, his performance is the metatextual rocket fuel that Black always needed to make his "bite the hand that feeds" riff on Hollywood excess go. Gibson was too green, Glover too earnest, Willis too jaded—Downey had the right mix of talent, pain, and cynicism to finally make Black's screenplay really come alive, and Black places him in scenes with top-tier comedic foils like Kilmer and Monaghan. The entire process elevates it beyond the groan-worthy sexism and gay panic that may charitably be interpreted as attempts at subversion, but read in 2021 as simply ignorant.

This was Black's comeback too: Downey would bring him into the Marvel fold with Iron Man 3, an exploration of trauma that reads as extremely personal for Downey—no wonder he brought along the guy who helped him through it in the first place. After that, Black made The Nice Guys as a sort-of spiritual sequel to Kiss Kiss, but it's more a comedy and lacks the hard edge that elevates its predecessor. 

Black also made The Predator, where all of his worst instincts were laid bare: The Predator has none of the cleverness and subtlety that mask Black's sexism and homophobia. Instead of a perfectly-timed, mid-2010s riff on the excess of Hollywood blockbusters and reboots, it's just a mean, out-of-touch slog that does nothing to advance the Predator's status as a sexual icon.

But that was in the future. In 2005, Kiss Kiss Bang Bang saved two careers, launched another, and gave western filmmaking one of the most watchable mockeries of its own culture that (I hope. God I hope!) still holds up to this day.

Also, it's a Christmas movie.