Classic Heist Films: An Appreciation

Lately, I’ve been watching a lot of classic heist movies, as research for a screenwriting project which everyone has already passed on before I even pitched it (a new record, even for me). I wanted to bring some love to this particular–sometimes wildly eccentric but also sometimes strangely consistent–slice of pop culture.

Using my own, arbitrary definitions, I decided the “classic” window extended from the 1950s to the 1980s, when moviemaking shifted from the auteur era to the Spielberg/Lucas “blockbuster” factory. I don’t have a great reason for this distinction, other than a feeling that, in becoming slicker, immaculately paced spectacle-fests, some of the quirky charm I enjoyed about these films went by the wayside. File under: Old Man Yells at Clouds.

One example of what’s fun to me about the old “heisters” is the differing ways they integrate criminal endeavors into the characters’ lives. Unsurprisingly, a few–like Dog Day Afternoon (1975), The Italian Job (1969), Thief (1981), and The Friends of Eddie Coyle (1973) – feature career criminals just taking on an unusually big new job. Although, I should note that Dog Day Afternoon and Thief in particular veer into particularly wide tangents into the protagonists’ everyday lives outside the crime – with the latter featuring an adoption subplot and the former, a tumultuous romance with a transgender lover (in 1973!).

But what’s unique about “the big heist” is, it’s not just about crime–it’s a work of human imagination, something that one no has ever tried before that promises a life-changingly huge reward, and implicitly, fewer of the grubby/dangerous downsides of everyday robbery. This appealing, adventurous, out-of-the-box prospect has a tendency to lure in “civilians.” In Ocean’s 11 (1961) it’s the challenge of knocking over five Las Vegas casinos in one night that reunites a band of World War veterans with the promise of “let’s carry out one more mission like in our glory days.”

The Thomas Crown Affair (1968) spins most of its drama (and romantic frisson) from the fun but odd premise of a caper masterminded by a rich, successful, but bored non-criminal. The mastermind behind the gambit in Topkapi (1964) insists on accomplices with no criminal record, to ensure the theft can’t be traced–an intriguing setting that unfortunately is not as plumbed for mishap as it could have been. And furthest from crime is Alec Guinness’ character in The Lavender Hill Mob (1951), an OCD straight-arrow treasury inspector who makes a huge 180 in his life and temperament–with wonderfully zany results.

Another layer of exploration that ranges across heist movies in how they answer the question: “Does crime pay?” Dog Day Afternoon is probably the least “heisty” of these in feel, as it focuses not on the plan, but almost entirely on its long, painful, and increasingly bloody failure. The Friends of Eddie Coyle also doesn’t seem to care about the heists, as the protagonist is only tangential to them while his life keeps spiraling downward. Thief plays with our heartstrings by seeming to line up the hero’s incredibly intricate scheme and plans for a new life, only to sadly sink both in the end.

But going back past the gritty 70s and 80s films, the earlier heisters play a more daring game: They want us to experience the maximum pleasure of rooting for the criminals to succeed, but then ultimately see their illegal endeavor fail. Topkapi, Ocean’s 11, and Italian Job take us all the way through an exciting “pulling it off,” only to maddeningly yank victory away through a detail gone awry in the very last moments of the film. The Lavender Hill Mob devotes an uproarious third act to the clever scheme unraveling in worse and worse ways. Only The Thomas Crown Affair (the one about the non-criminal criminal!) seems to let the thief get away with it the loot, though at the price of his potential true love.

Of course, one of the most enjoyable aspects of a heist movie is the sheer, mind-bending ingenuity of the scheme. As mentioned, the crimes proposed and (usually, more or less) carried out in these stories imaginatively transcend the conventional smash-and-grab. The Thomas Crown Affair involves precision-timing a group of strangers using only pay phones. The Italian Job requires throwing an entire city into a major traffic snafu. Ocean’s 11 necessitates multiple moving parts across Las Vegas. The Lavender Hill Mob features a scheme that sounds like something from a Warner Brothers cartoon. Topkapi is literally an agonizing acrobatics exhibition. Some, like Thief, simply imagine more innovative technical ways to break in and steal, but with an execution that’s mentally stimulating to watch.

Another fun aspect of many heist films is that their casting directors tend to throw in some curveball choices. Ocean’s 11 cast included most of the Rat Pack, and also a seemingly random “cowboy” character actor named Clem Harvey, who doesn’t seem to have done much else in Hollywood. Topkapi throws Peter Ustinov in with a bunch of other hard-boiled types, eventually making his bumbling comedy styles the center of the movie. The Italian Job is a Euro-sleek, sexy piece of intrigue that also includes…Benny Hill and  Noel Coward! Thief is a gritty Michael Mann potboiler featuring a tragic dramatic turn from…Willie Nelson? I don’t have something profound to say here, indeed it’s hard to discern a pattern, other than: It seems like the makers of heist movies wanted to telegraph “This ain’t your typical crime flick, toots.”

And along those lines – the “we’re not just depicting the act of theft, we’re having a lark” mentality – many heist films take some rather leisurely indulgences off of the main plotline. Topkapi is practically a Technicolor travelogue of Turkey, with an awful lot of non-narrative mass male mud wrestling. The Italian Job, unsurprisingly for a film centered on cars, is filled with all kinds of vintages both racing and getting crushed.

The Thomas Crown Affair features scads of romantic two-seater glider plane flying (including one sequence set to its Oscar-winning song, “Windmills of Your Mind”), none of which have anything to do with moving money or diamonds anywhere. And Oceans 11 has an entire non-diegetic Sammy Davis Jr. song and Dean Martin singing “Ain’t That a Kick in the Head” two-and-a-half times. Sinatra saves his crooning for the soundtrack, but he does get to try out some of his rather amusing “accent work.”

The post-80s slick factory remade Ocean’s 11, The Italian Job, and The Thomas Crown Affair. But I didn’t bother watching the remakes of latter two, because honestly, I didn’t feel the need. I thought their originals were dynamic and quirky enough to satisfy. But the OG Ocean’s 11, while clever on paper, is smirky and slow on film–we don’t even learn the plan until literally one hour in. To his credit, Steven Soderbergh’s 2001 remake doesn’t paper over the character eccentricities of the original – it replaces them with new ones. And it smartly builds on the “Ocean and his ex-wife” subplot that the original dangles but never pays off.

Ultimately, most classic heist films feature unlikely heroes crossing back and forth over the border of being anti-heroes, devilishly clever plans, and twisty approaches to conventions of law and order. All three are solid mechanics for making a film that delivers genre satisfactions, but also allows some genuine weirdness and individuality to creep in. In this way they model their subject matter: Pulling off the job in ways we could have never expected, even when nothing goes according to plan. No, make that especially.