What Makes a Good Heist Story?

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I know you know this feeling.

I scroll for hours through endless choices on any of the ninety-two different streaming services that I subscribe to since cutting the cord to save money on cable TV, which it doesn’t seem like I’m doing at all now. Most of my evening is spent looking for something interesting to watch while I’m racing to keep ahead of the autoplay preview before the pre-cranked volume blasts me into another room. I roll from screen to screen watching titles featuring familiar actors and actresses in starring roles for movies and television shows that I’ve never heard of even though I’ve worked in the entertainment industry for the past twenty years which usually means a) the project flew under the radar, b) the project sucks, or c) it flew under the radar because it sucks.  It applies across all genres.

The heist and caper genres are no exception. There were major boom periods in the early 1970’s and certainly throughout the 2000’s after the success of Steven Soderbergh’s Ocean’s franchise reinvigorated heist and caper stories with a fervor that still hasn’t gone out of fashion.  Hollywood loves repeating what works. You know how many Ma and Pa Kettle movies there were? (Ten. Eleven if you count The Beverly Hillbillies).  They’d film the phone book if they thought it would make them money.

Here’s what I look for in the heist and caper genres. For me, a book (or a movie/tv show based on a book) by a known author or one with a great track record, like an Elmore Leonard, Carl Hiaasen, or Janet Evanovich, is always a good start. It could be a fun, diverse ensemble cast in movies like Ocean’s Eight that draws me in, a genre-bending novel like The Lies of Locke Lamora or something new, fresh and hip like Edgar Wright’s Baby Driver.

Taste is very subjective, and I make no claims that mine is better than anyone else’s. There are many successful authors with fervent followings like Ally Carter and Leigh Bardugo that are simply outside my literary wheelhouse at this time. I’m fifty. Reading YA novels at my age is creepy.

Heists and capers are my bag; escapist fantasies that bring us inside worlds that most of us will never see. These are the people that embrace the hard sides of ourselves. The side that isn’t going to take any shit from anyone. The side who doesn’t care what some nebbish boss thinks of him or what the homeowner association is going to say. The person who’s willing to do whatever it takes for themselves, for justice, or for their family. They’re the people we wish we could be. Smooth. Slick. Sophisticated.

That said,  here are the things that I think make a good heist or caper story.


Good Heist Stories Have Good Hooks

In Ocean’s Eleven, George Clooney robs multiple Las Vegas casinos, watches Brad Pitt eating in every scene, and gets Julia Roberts in the end. In the book and movie versions of The Hot Rock, the gem John Dortmunder is after needs to be stolen again, again, again, and again. The Great Train Robbery had a Victorian England setting and a fictionalized version of a real-life crime. The Lies of Locke Lamora was a heist novel masquerading as a swashbuckling adventure. Each has a unique premise (a “hook”) that drew my interest without a lengthy explanation. I’ve always believed that if it can be described with one sentence, it’s a good hook. If it can’t, I’m going to be flipping back and forth between pages a lot, or asking, “Who is this? Do I like him?”

Good casting does not equate to a good hook. George Clooney would be the first to remind anyone that he did Batman and Robin, after all.

They Have Protagonists You Can Get Behind 

We like these people. We care about what happens to them. They strive for happiness, security for themselves or their family, and sometimes even revenge. These people have noble goals in their life, even if their methods to achieve them are less than noble. There is a vulnerability to them that elicits our empathy for their situation. We want them to succeed.  We want them to win.

Consider Mike, the young mute man from Steve Hamilton’s The Lock Artist, who suffered a horrible trauma as a child and has an exceptional talent for cracking safes and opening locks. There’s Joey Perrone from Skinny Dip who, after being tossed overboard on a cruise ship by her sleazy, conniving husband, seeks revenge against him but equally wants to know why her husband did what he did to her. The old men in both film versions of Going in Style turn to crime to fight off the fear, loneliness, and boredom that comes with growing old. Hard-edged protagonists like Parker in The Hunter may not garner sympathy, but Richard Stark made it easy to get behind Parker’s search for his money, his ex-wife, and his revenge. We want these people to be okay, and we want the people that do them wrong to pay.

The Protagonists Face Off Against Excellent Antagonists

A great hero is nothing without great opposition. While the natural opposition for any protagonist in the heist and caper genres is law enforcement, there is a tendency to relegate law enforcement to a secondary threat. Law enforcement has rules that they have to follow. For my buck, I like ruthless, credible opposition that goes outside the lines. It’s not going to be easy to defeat this opposition. These are the ones you want to see get theirs in the end.

I could feel the tension and the threat from Andy Garcia playing Terry Benedict in the Ocean’s movies. Even when he was defeated, you knew Benedict wasn’t giving up. He would pursue the people that wronged him to their dying days. I cringed at the slimy, scuzzy Chaz Perrone from Skinny Dip in his efforts to help enable those destroying the Florida Everglades, a man so corrupt that he would push his wife overboard a cruise ship to cover his bribe-taking ass. The same from the conniving Harvey Metcalfe from Jeffrey Archer’s Not a Penny More, Not a Penny Less, who was every single rip-off scam artist you’ve ever met wrapped up into one, and just the kind of person you’re hoping karma gives a big, fat hug. The antagonist doesn’t even have to be a person. The opposition in Donald Westlake’s The Bank Shot was the actual physical bank Dortmunder was stealing, and then what to do with it once he got it. Now that’s a solid antagonist.


They Encounter Big Risks To Get a Great Reward

Without them, you don’t have a book (or a movie). You have a sentence. The Hobbit would be much less exciting if Bilbo had done the trip for ten bucks and a box lunch. No one makes big plans to knock over a food cart or a 99 cent store. I want to these people stealing big, fat diamonds like in Snatch, I want to see them knock off the Charlotte Motor Speedway in Logan Lucky. I live in Los Angeles. I can see petty crime walking down the street.

They Offer a Social Context and/or Commentary

I’ve always liked the underdog. The person that fights against injustice, inequality, or the prevailing social order despite what might be considered a marginalized social position. Good heist and caper stories question our values, our thinking, what we consider to be important in our society, and who the good people and bad people really are. They show people stretching the limits of risk vs reward to escape their life circumstances or the limitations that society places on them. They look to better their lives, as we all do, and give us a voyeuristic insight into the bad things that can happen with the choices that we make.

Not everything needs to fall under this criteria. I like fun, dopey entertainment as much as the next dope. I loved the first National Treasure. Fast Five didn’t win any awards but doesn’t have to when it makes over $200 million dollars. The same with the remakes of The Italian Job and Gone in 60 Seconds. They might be cinematic one-night-stands, and I might feel a little dirty afterward, but they sure are fun. Just don’t expect me to acknowledge you in public.

People want to be entertained. It doesn’t matter how they get there, but that they get there. At least that’s what my wife tells me, but we may not be talking about the same thing.

I’ll be here until Friday.  Try the veal.


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