The more complicated the heist, the more interesting the story. Nobody wants to buy a ticket to a heist movie where the safecrackers break into a vault within five minutes and get away effortlessly with the loot (it’d also be a very short movie). Flicks in this subgenre are generally at their best when stuffed full of double-crosses, unexpected complications, and supposedly uncrackable security systems.
With that in mind, which heist films have presented their protagonists with the toughest and most unique challenges? These seven titles are memorable for a reason—what they put their respective criminal masterminds through is positively fiendish.
Rififi (1955)
The centerpiece of Jules Dassin’s French heist film is the sophisticated robbery of an upscale jewelry store protected by a sound-triggered alarm system. It’s a lengthy sequence conducted in near-total silence, with all the suspense generated by the thieves’ incidental noises: an accidental bump against a piano, the squeak of an ill-fitted screw, the muffled thump of a hammer wrapped in cloth.
The irony is that, despite those difficulties, the central heist goes much smoother for our intrepid, chain-smoking heisters than the aftermath, when the ringleader, Tony (a soulful Jean Servais), ends up snarled amidst murders and a kidnapping. For these characters, there’s no light at the end of this proverbial tunnel, just the chance to survive for another day in gray, rainy, working-class Paris. (And if you want a good example of a later director paying homage to Dassin, check out the first “Mission: Impossible” movie, in which Brian De Palma borrows the no-sound concept for Tom Cruise’s infiltration of an ultra-secure CIA facility.)
Heist Difficulty Rating: 7
The Italian Job (1969)
In most heist movies, the target is stationary: a vault, a safe, a building. “The Italian Job” subverts that conceit: the target is a convoy protecting a truck loaded with gold as it makes its way through the Italian city of Turin. Master thief Charlie Croker (Michael Caine) comes up with the idea of stealing the gold, loading it into three Minis, and zooming through the streets (and down stairways, and along sidewalks, and through malls…) to safety. The emphasis is on bombastic speed, not silence and deception.
Croker is a solid tactician who’s come up with a solid plan—except even on a quiet day, traffic in many Italian cities is memorably terrible. Successfully picking a safe, even a high-tech one, is far less difficult than trying to navigate past roughly a thousand overcaffeinated drivers idling in your lane, especially when there’s also a bunch of excitable Carabinieri right behind you.
“The Italian Job” has exerted a massive influence on heist movies for fifty years. For example, you can’t watch a “Fast & Furious” movie without seeing the obvious debts in structure, pace, and plotting—particularly the fifth one, in which Vin Diesel and Paul Walker use a pair of Dodge Chargers to drag an oversized vault through the streets of Rio at highway speeds. But the makers of “The Italian Job” didn’t have CGI, which makes all the stunts feel grounded and crunchy in ways that elude the movie’s descendants.
Heist Difficulty Rating: 8.5
The Good Thief (2002)
Your humble correspondent still stands by the idea that “The Good Thief,” a remake of Jean-Pierre Melville’s “Bob le Flambeur” (1956) starring Nick Nolte as a charming-but-seedy professional robber, is one of the best (and criminally under-watched) heist movies ever made. Nolte’s Bob, laying low in southern France, assembles a crew to break into a highly secure room containing some of the world’s greatest paintings. Like so many other heist films, much of the running time is devoted to figuring out how to bypass the room’s guards, locks, and next-generation alarm system—a quest made exponentially more difficult by a local cop named Roger (Tcheky Karyo), who develops a keen sense for what Bob might do next.
In fact, Roger’s so good at anticipating Bob that the latter decides an already-elaborate heist needs an additional layer, a distraction that will pull the police away from the villa containing the secure room. The nature of that distraction—and how it eventually impacts the fortunes of the heist crew—is what elevates “The Good Thief” above so many other films that present its antiheroes with similar challenges. Everything hinges on pure luck, the one thing outside even the most genius heister’s control.
Heist Difficulty Rating: 7
Inception (2010)
Many a heist film hinges on the conceit of the unreliable mastermind. They’re more than capable of putting together a decent plan for robbing a vault or armored car, but their own demons (a need for revenge, for example, or to reclaim a lost love) risk dooming the whole endeavor. Christopher Nolan’s “Inception,” which often plays like a heist film written by Freud, takes the idea of the unreliable mastermind to its most extreme.
Cobb (Leonardo DiCaprio) runs a crew of “extractors” who slip into a victim’s subconscious to steal valuable ideas. Early in the movie, they’re paid by Japanese businessman Mr. Saito (Ken Watanabe) to slip an idea (the titular “inception”) into the mind of a rival mogul’s son (Cillian Murphy). The resulting “heist,” which involves plunging through multiple layers of the son’s subconscious, offers Nolan the opportunity to play with a portfolio of noir and action-movie tropes, including an urban car chase in the rain, the infiltration of a luxury hotel, and a heavily militarized shootout at a mountain base that contains a large vault.
Each of those scenarios would be difficult enough for a group of dream-criminals to navigate—but Nolan throws in an extra complication by revealing Cobb as a secret basket-case, with his messy subconsciousness manifesting during the finale as runaway trains, a trigger-happy femme fatale, and more. Things implode spectacularly:
Anything can happen in a dream—which means a dream-heist can become infinitely difficult.
Heist Difficulty Rating: 9
Army of the Dead (2021)
Is Zack Snyder’s “Army of the Dead” a zombie flick that just happens to feature an intricate heist, or is it a heist flick that just happens to feature an entire city of slavering, curiously speedy zombies? Scott Ward (played by a gruff but curiously tender Dave Bautista) is given a tight deadline to assemble a team, sneak into zombie-riddled Las Vegas, and rob $200 million from a highly secure vault before the U.S. military unleashes a thermonuclear strike on the city.
Ward’s crew consists of all the lovable heist-movie clichés, including the brilliant but highly excitable safecracker (Matthias Schweighofer), a daredevil getaway driver/pilot (Tig Notaro), a taciturn badass (Omari Hardwick), and the shifty dude who inevitably betrays the group (Garret Dillahunt). From the film’s first frame, you know they’ll figure out how to bypass the vault’s supposedly impregnable security system… but will they all survive the friggin’ zombie tiger lurking outside the casino?
Heist Difficulty Rating: 10
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