A heist story turns its audience into the accomplices of a crime. Other stories ask us to like or empathize with their characters. A heist story asks us to discard the ethics and morals we abide by in our daily lives. The main characters are criminals, stealing something that was never theirs to begin with. But because they’re our protagonists, we find ourselves rooting for them to pull off a crime. They’re charming, smart, skilled, professional. And because we’re rooting for them, we begin to feel like one of them. We see things the way they do. We’re a member of the gang, and we want to pull off the job.

So it’s no wonder audiences have continued to enjoy heist stories in film, television and books. Perhaps only the gangster story allows its audience such an illicit, vicarious thrill. We may be goody two shoes in life, but when we enter the world of a heist story, we feel what it would be like to live and work as a criminal.

Fellow Anythinker Julie Crabb and I could talk about heist stories for hours. We have, in fact. So whether you’re a fellow fan or newcomer to this genre, we invite you to eavesdrop on this little digital conversation of ours as we discuss our favorite heist stories and try to figure out what makes them so damn irresistible. 

Julie: I think we should start with the book that began this conversation between us, Elmore Leonard’s Out of Sight. After devising a scheme to escape from prison through an underground tunnel, illustrious bank robber Jack Foley makes his getaway only to end up with an unexpected passenger: U.S. Marshal Karen Sisco, who just happened to be at the prison the evening of the breakout. Following a flirtatious scene in the trunk, the two cozied conversationalists part ways, and Karen is put on the team to track Foley and the other escapees. A cat-and-mouse plot ensues and the two wonder "what if" (a sexy time out scene between George Clooney and Jennifer Lopez that makes the film version a must see). Despite their connection, Foley makes his living robbing banks; Karen’s job is to put him away for it.

Now, I may have major issues with the meet-cute that fills the opening sequences as I don’t see the appeal of a stinky man in a trunk that just escaped through a prison tunnel, but I have to confess that I love a charming rogue – a character you find yourself rooting for even though you know very little about their backstory and what you do know should make you distrust them entirely. These characters are sexy, mysterious and, oh man, I just want to be one of them. 

Jeff: First of all, it boggles my mind that anyone could love Out of Sight but dislike its centerpiece scene! Yes, Foley is a stinky felon who unceremoniously cozies himself right up against his captive and eventual love interest. But he’s so suave, so at ease! Who wouldn’t be charmed by a man who flirts and talks about movies during a hostage situation? 

So it’s clear that Foley, and his felonious ilk, are charmers. Is that why you want to be one of them? The ability to walk up to a bank teller, calmly explain that this is a robbery, and walk away scot-free without ever having lifted a finger, let alone a gun?

Julie: It’s not that I want to rob a bank or murder anyone who gets in my way, but I do want the adrenaline that comes along with it. I want to feel the rush inside my veins. I love charming rogues because they seem to love themselves. The swagger and politeness of Foley, for example, mitigates the less-than-desirable aspects of how he plies his trade. The astute cultural intelligence of Neal Caffrey from White Collar obliges us to overlook the lies coming out of his devilishly handsome smile. The Old Man & the Gun gives us Robert Redford as Forrest Tucker, a 61-year-old smiling gentleman who has the ability to rob banks without ever drawing his gun. These characters make their way through the world using the skills they have and it is a pleasure to watch.

Jeff: So you seem to be arguing that it’s the characters themselves that draw us in. Like trickster characters in a folktale, the criminals of a heist story disregard traditional societal mores through guile and charm. They get away with what we can only dream about. That certainly is the case with Jack Foley. Or Danny Ocean of the Ocean’s series (or, really, any character ever played by George Clooney...talk about a charmer).

But there’s another aspect to the appeal of the heist story, and that’s the heist itself. The heist in a heist tale is always pleasantly convoluted. Alarms, trips and security cameras have to be circumvented, the loot has to be located, pilfered and in many cases fenced, and of course, the gang – or, occasionally, the lone wolf – needs a getaway plan. Money’s no good if you’re in prison or dead.

Rififi, the 1955 French crime film which I previously wrote about here, is one of the great heist stories of all time, and arguably the progenitor, along with The Asphalt Jungle (about which more later), of all heist films. The plot is simple – after serving a 5-year sentence for jewelry theft, an aging crook agrees to one last job with a small, committed team of cons –  but the heist is a precise, complicated, technical affair. The gang’s target is a Paris jewelry store and the loot is worth enough to set up the criminals for a long time. 

I wouldn’t dream of spoiling the details of the heist, but I’ve always been thrilled by how...doable it seemed. Which is to say, rather than employing highly sophisticated and specialized equipment, the gang makes use of items like an umbrella or a fire extinguisher in devious ways that help them pull off their crime. Obviously today’s security systems are far more complicated, but sometimes the best way to outwit something high tech is to go low tech (there are plenty of capers and heists in Breaking Bad and Better Call Saul that follow this dictum).

So for me it’s as much about the job as it is about the characters themselves. How much do you care about the actual heist in a heist film, Julie? Any favorite heists? 

Julie: While a charming rogue may carry the film, and the sly twists or doubled-back narratives make us squirm in our seats, the eccentricity of the actual heist is the frosting on the brownie. For me, it is a feat of filmmaking, the elegant pans and pivots, that reveal the plan in clockwork execution. Whereas you seem to enjoy a heist that is doable, I much prefer a plan with some theatricality and showmanship. For me, details are everything in a heist sequence, from the graceful bowler hat sequence in the 1999 remake of The Thomas Crown Affair to Joe Bang’s (Daniel Craig) explosive mixture of gummi bears, fake salt and bleach pens in Logan Lucky.

A heist that certainly fits the bill of extravagant production appears in Mission: Impossible. To discover a mole, Ethan Hunt (Tom Cruise) wants to steal the NOC list, a record of every secret agent and their true identity. We soon learn that the obstacles to entry include retinal scans, voice activation, temperature controls and a pressure sensitive floor. Each obstacle is addressed, accompanied by Lalo Schifrin’s propulsive theme pulling us into the fold. The viewer is given a front row seat as the team...

• uses first responder disguises to gain entry to the building,
• poisons the Langley employee using a ballpoint pen and applies a tracking device,
• snakes their way through air conditioning ducts using magnets and brute strength,
• blocks motion lasers, 
• cable drops Ethan into the room,
• gains access to the needed files, 
• and, oh yeah, bites a rat before making it out almost undetected. 

The skill set involved in these sequences are what really thrills me, whether it’s a lone wolf jewel thief a la John “The Cat” Robie (Cary Grant) in To Catch a Thief, or a team of individuals with highly specialized talents like we see in the Ocean’s series. The caper crew of a heist film is dependent on the tasks at hand, but often include the mastermind who orchestrates it all, the backer who finances the crime, the distraction (often a seductive lady friend), and other labor-oriented roles like safe-cracker, hacker, pickpocket, or the muscle. Vulture lists out “The 13 Best ‘Assembling the Team’ Movies” and each "getting the gang together" montage is unique in its makeup. Every member of the team has a role that must be carried out with exactness because teams are like machines; every part has to do its job or the machine won’t work. 

So, Jeff, if I needed to get the gang together, what role would you play?

Jeff: Well, having not participated in any heists (as of yet) it’s difficult to say what my role would be on the team. My gut instinct is to say the orchestrator, the one who susses out the target,  puts the team together, and creates the strategy for the heist and the getaway. I’m a big-picture person, but also enjoy thinking about details, so this role would seem to suit me best. It’s the writer in me, the world-builder. Though who knows? Maybe I would be the honeytrap. Who would you be? I’m betting on the munitions expert. 

Julie: While I do love an explosion, I would likely be the confidence man, manipulating the mark with lies and distraction. Do go on. 

Jeff: I like what you wrote about teamwork and the heist, but you got me thinking about the paradoxical dimension of a team heist. The team at its best is a well-oiled machine; you need each member and each skill set to pull off the job. But the team is also the reason heists so often fail. Teams are composed of humans, after all, and humans are pretty fallible creatures.

No heist story I can think of demonstrates this paradox better than The Asphalt Jungle, which pre-dates even Rififi and is certainly among the most influential heist stories of all time. Laying out the template that nearly every subsequent heist film would pilfer, The Asphalt Jungle follows a small crew as they plan and break into a bank vault.

The heist itself is certainly enjoyable (though not nearly as pleasantly convoluted as the heists the film helped inspire), but what distinguishes The Asphalt Jungle is the care and acuity of its characterization. “One way or another,” Doc Riedenschneider, the heist’s orchestrator explains, “we all work for our vice.” Doc himself has a creepy penchant for young girls. Alonzo Emmerich, the lawyer and ostensible fence, is torn between his bed-ridden wife and the alluring Angela Phinlay (Marilyn Monroe in her first major role). And then there’s Sterling Hayden’s Dix Handley, a self-destructive, debt-ridden felon whose weakness for gambling puts him on a treadmill of  never-ending crimes and convictions. He’s also so intent on cleansing himself of the “city dirt” and reclaiming his family’s farm in Kentucky that nothing, not even a bullet wound, will get in his way. All of these “vices,” play roles in the fates of the characters. No one steals simply for the thrill of it, The Asphalt Jungle seems to argue. Money is just a symptom of the disease.

And on that happy note, Julie, I want to ask if you like it when the criminals in a heist film fail? Is the almost inevitable failure of the criminals the reason we get away with watching and in some cases loving (or identifying with) characters who do morally questionable things? Or do you prefer those rarer instances, as in Ocean’s 11, where the cons walk scot-free?

Julie: If I have spent the entire film rooting for a cast of characters, I desperately want the plan to prevail. When a character is as likeable as George Clooney’s Foley or the plan as precisely planned as the team in Rififi, the real-life consequences slip my mind. The details have romanced me to believing in the good of the heist. However, I don’t necessarily want everyone to walk into the sunset either. I delight in a twist that uncovers a hidden loyalty like in the illusionist heist team of Now You See Me. I also relish a messy aftermath that provides a sort of comeuppance for the bad guys. For example, in Reservoir Dogs, we learn of a botched jewelry store heist through flashbacks and narration of the main characters, all of which leads up to a bloody betrayal in the film’s final shot.

Perhaps that is the rub: we may feel that we are accomplices in the crime during the planning stages and while it is happening, but we never have to deal with the aftermath. It is a vicarious thrill with a defined endpoint. The credits roll and we go back to being the goody two shoes we always were and can safely leave behind our temporary life of crime.

That’s it for us, Jeff, thanks for talking about the thrill of the heist with me. 

Jeff: My pleasure. Now let’s go rob a bank.