For the record, I am a sucker for a good heist picture, and a con is essentially a heist where the methodology comes down to human psychology rather than physical security. For that matter, I enjoy actual cons, or harmless ones, at any rate, from magic tricks to practical jokes to carnival games. If I may break into a tangent for one of my patented Random Anecdotes, when I was about 17 I went with one of my good buddies (Kingsley) and his family to Atlantic City to celebrate his birthday. We were both too young to gamble or drink but we enjoyed the all-ages attractions of the boardwalk, and at one point we found ourselves at one of the booths where the object was to throw a round wooden hoop around a square wooden block. It was a slow day because the weather was crappy, so the carnie working the booth spent a long time talking to us, which just allowed him to bleed that much more money off my friend. With Kingsley’s athletic inclinations, especially for sports requiring a certain amount of good aim, he felt like he should be able to make the toss. He didn’t, the first time he tried. So the carnie let him try again for free. Kingsley missed again. So the carnie offered to demonstrate how it was done, if Kingsley was willing to pay another dollar to try again after the demo. The carnie made a perfect shot. Kingsley tried to do exactly what he had been shown, and missed. The carnie offered to move the target closer. Kingsley lost another dollar. And so on and so on until the carnie had literally set up a small ramp on the front counter of the booth, with the wooden block at the end of the ramp, and had demonstrated (repeatedly!) how you could slowly slide the hoop up the ramp so that it fell down straight onto the block, and Kingsley tried to do it and couldn’t get it to work. I watched all of this unfold and was pretty much grinning ear-to-ear the entire time. And I admit, part of this was because Kingsley usually got his way in life (he was the oldest child and only son of fairly indulgent, affluent parents) and it was moderately hilarious to watch him grow increasingly incensed about wooden hoops and blocks. But mostly it was a very pure form of cerebral pleasure to watch the carnie do his thing and do it excellently, not just that he could get the dumb hoop around the stupid block (I knew there had to be some secret trick to that) but that he could keep up the constant patter and form that instant connection with Kingsley that made Kingsley feel like the carnie was on his side and rooting for him even as he kept remorselessly taking dollar after dollar out of his pockets. I can remember in that moment wanting very much to spend a whole summer doing that guy’s job, learning the trick of the game and running it for marks every day. It seemed like a blast.
Of course, that’s the beauty of a con movie like The Sting: the audience gets to see how the trick is done, how the ruse is constructed and executed, which is its own special kind of illicit thrill. And I give a lot of credit to The Sting for the smart ways in which it’s constructed. For one thing, despite the fact that the main characters are con men and grifters, we never have any problem giving them our sympathy or rooting for them to succeed. The initial con is pulled off against a low-level hoodlum working for a bigshot crime boss, after which we see the mentor-figure con artist at home with his loving family and vowing to give up the shady business. The bigshot crime boss vows revenge on the men who stole from him, and soon enough the mentor is dead and his protege (Redford) is swearing revenge against the crime boss. So the protege seeks out an old associate of his mentor’s (Newman) and they go in together against the crime boss. Redford and Newman are playing unrepentant thieves, but their ultimate target is a monstrous murderer. (Also, arguably, one of their targets is a cop forever harassing Redford, but he’s a corrupt cop, which makes him worse than a con artist.)
The con on the crime boss is massive, and actually involves two distinct phases: ripping off the crime boss a little, so that the crime boss becomes enraged and open to the idea of extracting payback of his own, and then utilizing that to lure the crime boss into an even higher-stakes scenario which is presented as an opportunity for payback but is strategically designed to backfire. This is fantastic storytelling because, on the one hand, you don’t go to a magic show to see a magician do one trick. So the audience gets more bang for their buck as the elaborate, multi-tiered plan unfolds. And on the other hand, it more than justifies the eventual triumph of Redford and Newman’s characters by giving them the space and time to play a long, slow, far-reaching game with their prey.
More importantly, there’s a delicate negotiation of trust with the audience. Phase one of the plan involves Newman cheating the crime boss out of a large sum of money in a poker game. It is established ahead of time how he is going to do it, and things more or less go according to plan. The satisfaction comes in watching a job well done, and also in the little details of execution which were not spelled out ahead of time but which make perfect sense as they unfold. As the second phase moves along, parts of how it is going to work are made clear but other parts are not, yet thanks to phase one the audience has no trouble going along with it, assuming that all will be explained. By the time the titular sting of the long con is being played out, the audience still has not been completely clued in as to how carefully everything has been arranged and scripted, which makes the climax genuinely nerve-wracking. The final explanations of how the con worked are brought to light only after everything has satisfactorily played out to its conclusion.
And on another level, the movie itself is a bit of a con being performed on the audience. There are misdirections on the character level which keep the audience guessing all along, seeming to suggest that the con could unravel in any number of ways. But by the end, it becomes clear that there was never anything to worry about.
Of course there are a few things I could nitpick about the movie. There’s a moment early on where Redford takes all his ill-gotten gains from the low-level hoodlum to an underground casino and makes a single reckless bet, which he loses. I get the characterization effect they were going for here, but you would think that someone who’s been living the life of a hustler would know that shady gambling dens have ways of rigging the games in their favor and that there was no way he was ever going to be able to win the bet, which makes it not just reckless but pointless. (And to get even more nitty-gritty: Redford bets thousands of dollars on red at the roulette table. Personally I love the outside bets on roulette, so that got my attention. The croupier tries to turn away such a large bet but one of the pit bosses tells him to take it, then gives him a signal. The croupier presses a button and the steel ball drops into 22 Black. Which, if memory serves, is the same number that the roulette ball lands in at Rick’s Cafe Americain when Rick signals his croupier (for much more benevolent reasons in Casablanca). All of which just made me wonder if The Sting was homaging the earlier movie, or if there was a company in the 1930’s that made rigged roulette wheels which all had the magnet under 22 Black, in which case if it was in widespread use Redford’s character definitely should have known that and should have bet on black!) Another nitpick would be that the climax of the long con depends on certain special effects which struck me more as the domain of 70’s Hollywood than 30’s Chicago hustlers.
But I wouldn’t let those minor flaws detract from the fact that The Sting is a gloriously watchable movie. Redford is solid and Newman positively steals the show, while Robert Shaw as the crime boss they pull it all over on is everything you could want in a villain. There may not be a lot of profound depth to the movie, or life-altering insight into the human condition, but to anyone who enjoys watching how complicated machines are put together and how they work, the appeal is undeniable.