9 Movies That Celebrate The Art Of The Heist In All Its Forms

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Heist films are an art unto themselves. They often overlap other genres – crime, thriller, film noir, romantic comedy – but the central element is, must, and will always be the perfect heist. The planning and the execution must be perfect, the criminals charming (most of the time), the take lucrative, the baddies so very bad, the mark someone or something we love to hate. A well-planned heist is cinematic poetry – it has tension and cleverness and at its best keeps the audience guessing right up until the end.

It is far too easy to go wrong in a heist movie – over-complication can be as bad as oversimplification, and tricking your audience at the last minute happens too often in the lesser films of the genre. But when a heist film works, when all the elements come together, what fun it can be!

To celebrate the release of Danny Boyle’s Trance, here are nine movies that celebrate the Art of the Heist, in its many forms.

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How To Steal A Million

how to steal a million 9 Movies That Celebrate The Art Of The Heist In All Its Forms

The mid-60s were a time for great heist films. They brought us dashing crooks who drove fast cars, drank champagne and robbed people almost as an afterthought. How To Steal A Million trades on the frothy cred of the high-society burglar that began with Ernst Lubitsch’s Trouble In Paradise and was carried on via Cary Grant in To Catch A Thief.

The cast alone gives it credibility: Peter O’Toole is dashing art thief Simon and Audrey Hepburn is Nicole, the law-abiding daughter of an art forger (Hugh Griffith). Together they must pull off a brilliant heist – to steal a well-protected statue from a gallery in Paris, before it can be discovered that the statue itself (on loan from Hepburn’s father) is actually a forgery.

As with many heist films, How To Steal A Million does not merely concern itself with the theft of the statue. It sets up a whole slew of entertaining and charming characters: millionaire Eli Wallach who plays an unwitting role in the heist, a museum guard known only in the credits as ‘Mustaches,’ an ongoing joke about waking up the President of France in the middle of the night.

The heist itself is clever and remarkably low-tech, involving a boomerang, a loaf of bread, an elaborate alarm system and O’Toole and Hepburn pressed together in a broom closet. With a quintessential Sixties soundtrack, gorgeous clothes, fast cars and two leads who could charm anyone’s pants off, this film is the frothy genre at its height. Makes you want to be an art thief.

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gambit 1966 670x282 9 Movies That Celebrate The Art Of The Heist In All Its Forms

Exhibit B for the 1960s: Gambit, starring Shirley Maclaine and Michael Caine, who give Hepburn and O’Toole a run for their money in the charm department. This time high-society is infiltrated by a dance-hall girl and a Cockney thief, posing as a wealthy aristocratic couple from Hong Kong. Maclaine is hired by a thief Harry Dean (Caine) to impersonate the deceased wife of millionaire Ahmed Shabandar (Herbert Lom) – or rather, a woman who looks like his deceased wife, in order to gain the millionaire’s confidence. Harry’s rather circuitous plot is all set up to steal a priceless statue from Shabandar’s apartment.

I hate to spoil the game with Gambit, so let me just say that you have to experience it from the very beginning and be patient. Maclaine is all but silent for the first half hour; after that she does not shut up. Nothing will goes exactly as planned – Shabandar is far from an easy mark, and Harry’s cred as a proper thief is very much in doubt. The film manipulates audience expectations, letting us know from the start almost exactly what Harry is up to. The tension derives from how it all departs from his original plan. Maclaine proves to be more clever than the thief, a circumstance which drives him crazy. There is also a sweet romance boiling just beneath the surface that complicated matters.

And the heist? Let’s just say that Catherine Zeta-Jones in Entrapment has nothing on Shirley Maclaine’s limber limbs.

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entrapment 540x360 9 Movies That Celebrate The Art Of The Heist In All Its Forms

Remember when Sean Connery did fun movies and Catherine Zeta-Jones was in them? Yeah, those were the days.

Entrapment borrows heavily from Gambit, but with very different results. Connery and Zeta-Jones are thieves (or are they?) working together (or are they?) to first steal a mask from an art museum, and then several billion dollars from a bank in Kuala Lumpur. The first job is pretty much an excuse for Zeta-Jones to show off just how limber she is, but wins points for being elegant and tense. Most of the tension of the film, however, comes from the bait-and-switch that both of the main characters play at: who is entrapping whom and why? This is a heist film in which neither the characters nor the audience are certain of who to trust, or how the various angles are going to work out. The romantic implications are similar to those of Gambit and How To Steal A Million, but here we’re uncertain about the motivations and loyalties of our heroes. It’s perfectly possible that they’re both out to screw each other over.

Enjoyment of Entrapment is heavily predicated on the idea that you actually like the two leads, and like them together. I do. The twists and turns work because the film never dwells on them long enough to make the audience consider them in depth. It is not a film to stand up again too close scrutiny, but has a charm all its own. One of the better contemporary heist pictures.

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sneakers 9 Movies That Celebrate The Art Of The Heist In All Its Forms

Sneakers is another (more) contemporary heist film with the added twist that the criminals are actually working for the government. Robert Redford is Martin Bishop, a former computer hacker turned security consultant, along with his rag-tag team of criminally inclined misfits (a cast including Dan Aykroyd, Sidney Poitier, River Phoenix, and David Straithairn). They’re hired by the NSA to steal a ‘black box’ supposedly developed for the Russian government. All is not as it seems, however, and pretty soon everyone is in a lot of trouble and … things get really complicated from there on out.

There are several heists in this heist film and both are in the ‘Oh my God, they’re going to get caught!’ category, ratcheting up the tension via the exterior movements of other characters. Unlike the other films on this list, it is not entirely clear why the heists need to be pulled off at any given moment. The audience knows about as much as the criminals do. There are the requisite early-90s computer things going on, but thankfully the heist is largely accomplished through intellect and not through high-tech gadgets.

The cast really make the film, glossing over some of the more ridiculous edges and injecting some very necessary charm into the proceedings. Due to the computer-tech angle, Sneakers is almost more dated than the 60s films on my list. Thankfully we have Robert Redford to keep us interested.

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Ocean’s Eleven

george clooney brad pitt oceans eleven 001 547x360 9 Movies That Celebrate The Art Of The Heist In All Its Forms

I think it’s a requirement to include Ocean’s Eleven on any heist movie list. Although I badly want to dislike Clooney and Pitt, and their cooler-than-thou attitudes, I just cannot do it.  Let’s face it – Ocean’s Eleven remains one of the best contemporary heist movies, bar none.

When I say “original,” I am not talking about the frankly dire excuse for Frank Sinatra and the Rat Pack to hang out, but the highly enjoyable excuse for George Clooney and his Rat Pack to hang out. Ocean’s Eleven has all the ingredients that we want from a ice-cool heist movie: great baddie (Andy Garcia at his smarmy best), cast of eccentric and clever criminals (my personal favorite is Elliot Gould), a lot of good-looking men in suits, and the perfect take: ripping off a Las Vegas casino. No one can feel bad about seeing a ludicrously wealthy industry beaten at their own game.

All great heist movies require a strong plot – and if they include twists, those twists had better be believable. I have to admit that I was guessing throughout this entire film. The charm of the leads might carry it, but without the very clever plot construction beneath there would not be much to say.

It gets further points for not dwelling too long on Clooney being Clooney – every member of the team has an important role to play and gets their due.  While the sequels became increasingly ridiculous and confusing – although still fun – Ocean’s Eleven is at the top of the genre.

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The Killing

Film 575w TheKilling 9 Movies That Celebrate The Art Of The Heist In All Its Forms

Then there are the heist films that remind us that stealing things is not always fun and games and thieves not always dashing gents in nice suits, but violent criminals.  Stanley Kubrick’s The Killing gives us a daring, violent and very tense robbery, from planning to execution to aftermath.

The Killing follows the usual trajectory of heist films: the introduction of the criminals, the ‘getting the gang’ back together, our hero and the woman he loves, the planning stages, and finally the heist itself. The characters are fairly straight-forward and identifiable films noir types, played by noir actors: a corrupt cop (Ted de Corsia), an inside man (Elisha Cook Jr.), an elderly thief (Jay C. Flippen), the bad girl (Marie Windsor), the sharpshooter (Timothy Carey), the criminal who plans to make one last big score and then retire (Sterling Hayden). This is not a recipe for success, though.

The Killing takes interest not just in the crime itself, but the psychology behind it. Things do not start to go badly because of lack of planning, but because of the psychological make-up of each of the criminals, their foibles and failings and successes. The heist of two million dollars from a race-track is clever and tightly conceived, involving a combination of good timing and lucky (or unlucky) coincidence.

What makes The Killing a great heist film is the balance of strict planning and the psychology of each member of the team, creating an almost nihilistic paradigm in which this heist can only end one way. It’s the getting there that is so fascinating. The Killing is brilliant and taut, without ever exceeding itself. It is the dark side of the heist.

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Le Cercle Rouge (The Red Circle)

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French films of the 60s and 70s were adept at taking quintessentially American crime stories and putting them in a French setting – they invented the term for film noir, after all. Le Cercle Rouge feels like The Killing re-adapted for post-war France, with a heady dose of  existential angst thrown in for good measure.

Alain Delon, Yves Montand and Gian Maria Volonte are career criminals from very different backgrounds out to pull-off an elaborate and seemingly impossible heist from a high-end jewelry store. On their trail is Commissaire Mattei (Andre Bourvil), as likable a police investigator as you’ll ever find in a heist film. The boys run afoul of underworld and police alike, sometimes via coincidence, sometimes via their own poor decision-making.

Like The Killing, the outcome of Le Cercle Rouge is almost a foregone conclusion, but it’s fascinating how they get there. The slow-burning story takes a great deal of time to set up our characters, playing with sympathies and the inevitable coincidences (or acts of fate) that bring the characters together. It also includes one of the tensest heist sequences ever committed to film – a good twenty minutes entirely without music or dialogue, as the plan unfolds before the audience. I honestly wanted to get up and applaud.

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 The Great Train Robbery

great train robbery 9 Movies That Celebrate The Art Of The Heist In All Its Forms

1979’s The Great Train Robbery (or The First Great Train Robbery, so as not to confuse it with the 1903 film) brings together three things that I love: heists, mid-19th Century facial hair, and Sean Connery. How can you go wrong?

Edward Pierce (Connery) makes plans to steal a shipment of gold from a London train, enlisting his good friend and cracksman Robert Agar (Donald Sutherland, with the most spectacular set of whiskers EVER) for help. Together they must obtain four keys to open the safes in which the gold has been stored, avoid being found out by the cops, and then actually succeed in breaking into a moving train and heisting a lot of gold.

The Great Train Robbery is a masterpiece of criminal ingenuity. As one thing after another changes, or goes wrong, our heroes must improvise – and the audience has to keep on their toes just to keep up. Nor is the theft itself the whole point of the film – most of it is taken up with just trying to get ahold of the requisite keys. One tense and all but silent sequence has our boys trying to obtain a wax impression of a key as the seconds tick by and we watch the authorities get closer and closer. There is also a requisite run across the top of a moving train, a sequence in a Victorian brothel, and several daring escapes, just to get your action jollies in.

It’s a dashing, laddish little caper movie about charming Victorian criminals. There’s nothing not to like about it.

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The Italian Job

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I had to save the best for last.

Michael Caine made an early career out of playing slightly incompetent but very confident criminals. Case in point: the fabulous original The Italian Job, from 1969. Not just an excuse for flashy cars and styling Sixties chicks, The Italian Job pits Charlie Croker (Caine) and his mob against the Italian Mafia, as they attempt to steal four million dollars through a traffic jam.

The Italian Job is the film that anyone making a heist movie should study first. It largely avoids explanatory dialogue, but you never feel lost or confused. The surprises, when they come, feel natural.  This is not a film that tries to fool its audience. Caine and Noel Coward, as the master criminal Mr. Bridger, orchestrating things from the inside, provide two counterpoints of quintessential Englishness – the brash Cockney upstart, in his wide ties, flashy Aston Martin and swinging bachelor pad – and the staid English gentleman, his jail cell decorated with pictures of the Queen.

My one objection is the lack of a cool female to cut through some of the macho overtones– was Diana Rigg not available? The Italian job itself, set against the backdrop of an England/Italy football match and executed using Mini Coopers, is set up just to prove that English criminals are far more stylish than Italian ones. The heist is not exactly poetic, but the extended chase sequence is, as the Minis outrace and outmaneuvre the Italian Fiats through the city of Turin to the tune of an English football chant. This is a ballet of driving – anyone who has ever wanted to race a Mini should take note.

The ending of The Italian Job is more than famous, but I will not blow it for anyone who has yet to see this masterpiece of British cool. We would all love to know what Croker’s idea was.

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To catch a thief Kelly kissing Grants fingers 9 Movies That Celebrate The Art Of The Heist In All Its Forms

These are by no means the only heist films available; there’s also Trouble In Paradise, To Catch A ThiefLock, Stock and Two Smoking Barrels, The Bank JobDuplicity, The Taking Of Pelham 123, and countless others that bring together all the fun of fast cars and sexy dames with all the excitement of international fraud. But so few contemporary heist films really give us the art of the heist as it is meant to be: cool, sexy, noirish, flashy, elegant, mind-boggling.

Danny Boyle’s Trance might well bring us back to the heist as the height of crime thriller, as well as art. The film is already out in the UK and it hits US theatres on April 5th. Until then, just remember that you’re only supposed to blow the bloody doors off.

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