Classic Heist Movies: A Tribute

I’ve been watching a lot of classic heist movies lately as research for a screenplay project that everyone had rejected before I even pitched it (a new record, even for me). I wanted to give some love to this special – sometimes extremely eccentric, sometimes oddly consistent – piece of pop culture.

Using my own arbitrary definitions, I concluded that the “classic” window stretched from the 1950s to the 1980s, when filmmaking was moving from the auteur era to the Spielberg/Lucas “blockbuster” factory. I have no good reason for this distinction, other than a feeling that as the movement moved toward more sophisticated, immaculately paced spectacles, some of the quirky charm I enjoyed about these films was lost. Filed under: Old man yelling at clouds.

One example of what I enjoy about the old Heisters is the different ways in which they incorporate criminal enterprise into the lives of the characters. Not surprisingly, some of them – such as Dog Day (1975), The Italian Job (1969), Thief (1981), and The Friends of Eddie Coyle (1973) – involve career criminals just taking on an unusually large new assignment. However, I must note that Dog Day and Thief delve particularly deeply into the protagonists’ everyday lives outside of crime – the latter containing a subplot about adoption and the former a tumultuous romance with a transgender lover (1973!).

But what’s special about “the big heist” is that it’s not just about crime – it’s a work of human imagination, something no one has ever attempted before, promising a life-changing, huge reward and, implicitly, less of the dirty/dangerous underbelly of an everyday heist. This appealing, adventurous, unconventional prospect tends to attract “civilians.” In Ocean’s 11 (1961), it’s the challenge of robbing five Las Vegas casinos in one night that brings a group of World War II veterans back together with the promise: “Let’s do one more mission like in our glory days.”

Thomas Crown’s Escape (1968) spin much of their drama (and romantic tension) from the funny but odd premise of a crook plot being planned by a rich, successful but bored non-criminal. The mastermind of the gambit in Topkapi (1964) insists on accomplices with no criminal records to ensure the theft cannot be traced – an intriguing scenario that, unfortunately, does not contain as many misadventures as it could have. And furthest removed from crime is Alec Guinness’ character in The Lavender Hill Mob (1951), an obsessive, no-nonsense revenue inspector who makes a huge U-turn in his life and temperament – with wonderfully wacky results.

Another level of exploration that extends across heist films is the way they answer the question, “Does crime pay?” Dog Day Afternoon is probably the least “heisty” of this type, 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 peripherally involved with them as his life spirals ever downward. Thief plays with our emotions by seeming to balance the hero’s incredibly complicated plan and his plans for a new life, only to sadly end up ruining both.

But if we leave the gritty films of the 70s and 80s behind us, the old gangsters play a more daring game: they want us to have the maximum pleasure of congratulating the criminals on their success, but then we see their illegal venture fail. Topkapi, Ocean’s 11 and Italian Job take us through an exciting “go through” only to snatch victory from us in an unbearable way by a detail that goes wrong in the very last moments of the film. The Lavender Hill Mob devotes a hilarious third act to the clever plot that unravels in increasingly dire ways. Only in The Thomas Crown Affair (the film about the non-criminal criminal!) does the thief seem to get away with the loot, albeit at the cost of his potential true love.

Of course, one of the most entertaining aspects of a heist movie is the sheer, unfathomable genius of the plot. As mentioned, the crimes planned and (usually more or less) carried out in these stories go imaginatively beyond the conventional burglary and robbery tale. “Thomas Crown” involves timing a group of strangers using only pay phones. “The Italian Job” involves throwing an entire city into massive traffic chaos. “Ocean’s 11” involves numerous moving parts throughout Las Vegas. “The Lavender Hill Mob” involves a plot that sounds like it came out of a Warner Brothers cartoon. “Topkapi” is a torturous acrobatic display in the truest sense of the word. Some, like Thief, simply imagine more innovative technological ways to break in and steal, but with an execution that is mentally stimulating to watch.

Another funny aspect of many heist movies is that their casting directors tend to make some surprising choices. The cast of Ocean’s 11 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 into the movie with a bunch of other tough guys, ultimately making his bumbling comedy style the focus of the film. The Italian Job is a European-chic, sexy intrigue movie that also stars… Benny Hill and Noel Coward! Thief is a dark pulp movie from Michael Mann with a tragic dramatic twist from… Willie Nelson? I don’t have anything profound to say about this, it’s actually hard to see a pattern except: it seems like the makers of heist movies wanted to signal, “This isn’t your typical crime thriller, honey.”

And in that spirit – the “we’re not just showing the theft, we’re having fun” mentality – many heist movies take some more leisurely digressions from the main plot. Topkapi is practically a Technicolor travelogue through Turkey, with a lot of non-narrative mass mudslinging between men. The Italian Job is, unsurprisingly for a film about cars, full of all kinds of vintage cars racing and being wrecked.

There are plenty of romantic flights in two-seater gliders in “The Thomas Crown Affair” (including a sequence featuring the Oscar-winning song “Windmills of Your Mind”), but none of it has anything to do with transporting money or diamonds. And in “Oceans 11” there is an entire non-diegetic song by Sammy Davis Jr. and Dean Martin sings “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 “accents.”

The post-’80s slick factory has remade Ocean’s 11, The Italian Job and The Thomas Crown Affair. But I haven’t seen the remakes of the last two because, frankly, I didn’t feel the need to. I found the originals dynamic and quirky enough to be satisfied. But the original Ocean’s 11, while clever on paper, is smug and slow on film – we don’t find out the plot until literally an hour in. Steven Soderbergh’s 2001 remake doesn’t gloss over the original’s character eccentricities, but replaces them with new ones. And it cleverly builds on the “Ocean and his ex-wife” subplot that the original teases but never delivers.

Ultimately, most classic heist films feature unlikely heroes who straddle the line between antiheroes and devilishly clever schemes, grappling with the conventions of law and order. All three are solid mechanisms for making a film that offers genre satisfaction but also injects some genuine craziness and individuality. In doing so, they shape their theme: pulling off the job in a way we never expected, even when nothing goes according to plan. No, make that particularly.