I love heist movies because they are that subset of crime film where the characters tend to be folks who are so smart and so skilled that were they of a lawful bent, they could have a long, happy, successful career plying their trade. But there is something about them that makes such a simple life impossible. Maybe it is a deep and persistent disdain for normality. Maybe it is a commitment to a vocation that just happens to be illegal. Maybe they have been burned so badly by the law that they have decided to live outside of it. Maybe they just like to take on challenges that put their skills to the test, with zero margin of failure—succeed or go back to prison. Maybe they are doing it for revenge. Maybe they are doing it for love. Or maybe, as is the case of Ocean’s Eleven, they are doing it for all of those reasons, and more.
Among heist films, Ocean’s Eleven is, for me, the gold standard. It is not a perfect film, but it is an enormously fun one and one that never seems to take itself too seriously. It’s got all the ingredients that make a crime movie fun—namely, the movie is not a blueprint for real-life villainy, the protagonists are likeable rogues who are preying upon sincere bad guys, and nobody resorts to violence. I am a guy who likes his violent films, but in a heist movie, the point of the action is to prove that in a world where you could take what you want by brute force, the better folks resort to their wits and their skill. It’s a different kind of story, and it’s one that you don’t see all that often—especially compared to other kinds of crime movies—in part because they are so hard to write. After all, what is a great heist movie without a great heist? And what is a great heist, if not brilliant and unexpected?
Criminal mastermind Danny Ocean (played with killer style by George Clooney) has just gotten out of a stint in prison and goes right back to work, planning the simultaneous robbery of not just one, not just two, but three Las Vegas casinos. We eventually learn that in a way, the casinos aren’t really the target. There is something personal at hand here, which both raises the stakes of the caper, and makes it that much more difficult to accomplish. Even by movie standards, we see right off that Ocean’s plan is so wildly ambitious as to enter the realm of fantasy, and that’s what Ocean’s Eleven is, really, and why I like it so much. It is a criminal fantasy movie.
Ocean sets about assembling a large team of highly skilled and specialized criminals for his master plan. Some of them he has a long and friendly history with. Others he has to convince to join him. But join him, they do, and once the team is united, the movie sets about executing Ocean’s plan, with each of them putting their unique skill set on display: subterfuge, gymnastics, technical trickery, pickpocketing, whatever.
If there is any weakness to this movie, it is that with a cast so large and high-powered as this one (Ocean’s team consists of, among others, Brad Pitt, Matt Damon, Don Cheadle, Bernie Mac, Elliott Gould. Andy Garcia and Julia Roberts also have their parts to play) that we really don’t get a chance to see any of these characters progress. We have just enough time to watch them do what they do, and we are meant to understand that for this story, that will have to be enough. Thankfully, for me, it was. These characters are all caricatures of a sort, but they are such fun caricatures that you don’t mind their one-dimensionality. After a while, you do start thinking of them not as their characters, but as actors who play them (even now, I can scarcely remember what most of the characters’ names are), but that’s alright. All you really care about is whether they’re going to pull off this bananas plan of theirs. Not to give anything away, but my moment of truth in this movie is a critical juncture when the whole thing very nearly falls apart because Danny Ocean overlooks one small detail. It’s always the little things that get you.
I love this movie because it manages to hold together despite having a really ambitious ensemble cast that under less skilled writing, acting and direction could have collapsed under the weight of itself. I love it that it enforces the characters with a number of little gimmicks (Brad Pitt never quite finishing telling Matt Damon his bits of advice; Casey Affleck routinely tormenting his brother) without the movie ever feeling gimmicky. I love it because there is a sense of irreverent fun throughout that elevates this thing from a mere robbery to a genuine caper. I love that the movie accomplishes this largely by staying true to its roots as a Rat Pack movie, while never trying too hard to draw upon the style of a bygone age. And I love that the movie hinges upon a plan so complicated in its execution that it could all feel like some dumb Rube Goldberg machine, but somehow, it never really does.
A deeper movie would spend more time wondering about what life would be like if they actually succeed, but you get the sense that even the guys in the crew haven’t really thought it out that much, themselves. To that extent, the audience is in the same boat as the characters. All you can do is hope for the best for these people, even if you know that chances are, it’s not going to come to them. People like this never retire. They just keep at it until they get killed or go to prison. But in the world of Ocean’s Eleven, somehow that grim truth never ruins the fun. It just lets you know that there will be further adventures, and you watch the credits roll, silently thankful for it.
To me, a lot of this movie was about the notion that you can attract the best team of specialists, with people uniquely qualified to fulfill their role, but it doesn’t mean shit unless they can improvise when things go south. Letting people do what they do best and making sure everybody plays their part without stepping on one another’s toes is great, but you need people that can collaborate when things *don’t* go according to plan and still get the job done. Sort of a philosophy of managing a startup. 😉