There is nothing quite like a great heist story for pure awesome escapism. You can create a fun and spine-tingling escape sequence, ala The Italian Job or Oceans Eleven. Or, you can be Breaking Bad, and use the format to break the audience’s collective heart. But in the end, they’re just about the teams, and the way all these weird skills like lock-picking, acrobatics, phone phreaking, and Cockney Rhyming Slang can come in handy in tight situations.
With some help from your answers on Twitter, here’s a list of some of the best capers in film, television, and literature!
The Italian Job and The Sting
These are the classic, ur-heist movies that set the standards for the list that follows. In each you’ve got charismatic protagonists—Michael Caine’s Charlie Croker and Robert Redford’s Kelly Hooker respectively. You’ve also got truly vile villains, in each case an underworld kingpin whose hatred of the grifter quickly turns personal. The real psychological drama of these films isn’t about the heists themselves—which are intricately plotted and run like clockwork — but rather the protagonist’s own desire to pull off something extraordinary. In The Sting, the tension lies in Kelly’s mounting recklessness, and in The Italian Job, we get a literal cliffhanger and one of the greatest endings in film history.
The Dortmunder novels—Donald E. Westlake
John Dortmunder stole the motto on his family crest, and he chose well: “Quid lucrum istic mihi est?” (“What’s in it for me?”) is an excellent moral to live by if one is a thief. Dortmunder is a small-time “planner,” arranging heists with teams that are only as large as they have to be, and usually only scoring small amounts of money. Dortmunder’s in his early 40s, his hair is thinning, he almost never smiles, and he has two strikes against him already. But he’s been strong enough to star in 14 novels over the last forty years, so he has that going for him...
William Gibson’s landmark cyberpunk novel is also a heist story. Henry Case is recruited by Molly Millions to steal a ROM module for a mysterious man named Armitage. This caper’s a little different, though, because the module contains some unusual loot: the uploaded consciousness of a cyber-cowboy named McCoy Pauley. The whole theft is engineered so that Armitage can have access to the best possible hacker; I would never advocate a life of crime, but if you’re going to go black hat, doing it to steal someone’s consciousness for hacking purposes has a certain style to it.
The Usual Suspects
Speaking of style... Bryan Singer’s second full-length film with writer Christopher McQuarrie pushed the elegance and verbal acrobatics of the movie so far that it didn’t really matter that the plot itself was pretty flimsy. Here the incredibly convoluted boat heist and loot (which changes from jewelry to heroin to cocaine to money over the course of Verbal’s story) really just serves as a skeleton for sharp writing and hilarious characterizations by Gabriel Byrne, Kevins Pollack and Spacey, and Benicio del Toro. By the end of the film we’re still not sure what actually happened, because Keyser Soze doesn’t really want us to. Some could see this as a flaw, but since this movie gave Singer enough of a name to go on to make the X-Men films, there will be no quibbling here.
Aww, this movie. This movie is so elegant, and so much fun, and it was written by the same guy who wrote Wargames, and Redford and Poitier are impossibly suave, River Phoenix is adorably nerdy, and the words “phone phreaker” and “conspiracy theorist” are used as compliments. Plus, Stephen Tobolowsky is in it! The basic plot centers on a pair of liberal former activists who get together for “one more heist” after twenty years. There’s lots of intrigue about whether one is betraying the other, how much they’ve each reformed, etc., but none of that matters. The important thing is that everyone on Redford’s team would be the nerdy tech guy in a normal movie, and they’re all lauded for being the nerdy tech guy. Not only is the film a solid piece of storytelling, it also celebrates intelligent people who use their wits.
Brad Pitt does his funniest work since True Romance, there’s some stuff about trying to track down a stolen diamond, a whole subplot about Irish bare-knuckle boxing, and some Irish Travellers who need to re-home their dahgs. There might be a plot under there somewhere, but does it really matter?
It’s not even remotely genre, but this is the remake of the classic-but-not-nearly-as-good Rat Pack movie must be mentioned. George Clooney wanders around Vegas charming people and spontaneously healing them with his smile, while his team—who between them have pretty much every weird niche talent you wanted when you were ten years old—robs his ex-girlfriend’s new boyfriend’s casino. Then there were sequels which gradually diminished the returns, but the films are still notable for making Las Vegas look like the high-class, hedonistic wonderland it has never actually been.
The Lies of Locke Lamora—Scott Lynch
Locke Lamora’s whole life revolves around heists. As an infamous thief and the leader of a brotherhood called the Gentleman Bastards, he has to stay ahead of the law and, more importantly, the underworld. But when a coup threatens his career, his way of life, and everyone he loves, he has to find a way to outwit the powerful Gray King before he becomes a pawn in a larger game.
Mistborn: The Final Empire—Brandon Sanderson
The Mistborn series begins a thousand years into the reign of a Dark Lord who was actually competent enough to vanquish the prophesied Hero. So, with a beginning like that, Sanderson could have gone anywhere, but he decided to graft a caper onto a fantasy structure. In his own words:
“I came into this book with two big ideas for the plot. The first was that of a heist story, like Sneakers or Ocean’s Eleven involving a gang of gentlemen thieves who each had a distinctive magic power. I wanted to tell the story of how their different magics and abilities worked together for them to pull an incredible caper.”
Breaking Bad, “Dead Freight”
Oh, Vince Gilligan, why do you hate us so much? Or possibly love us? We don’t even know anymore. “Dead Freight” is a stand-out BB episode, wherein Walt, Jesse, and Todd blockade a train in order to siphon methylamine from its tank. But, this is Breaking Bad, so what begins as a sort of tense and exciting escapade turns into an examination of Walt’s desperation, and ends on a heartless—but necessary?—act. Yay, humanity! Come on, Vince Gilligan! Would it have been so harmful to your vision to give us a Mini Cooper chase through the desert instead?
There was no way to fit everything in this list, so let me know about your own favorite fictional heists in the comments!