1. The Usual Suspects (1995): This is one of my favorite films, and it also happens to be a heist film. With a truly brave screenplay that could have completely turned audiences off as you know almost nothing when the film ends, massive doses of ambiguity throughout, great actors giving great portrayals and a talented director at his best, this one is not to be missed. Here's an interesting thought too, what if Keyser Soze is Satan and the film is actually supernatural?
2. Ronin (1998): This is easily the best spy film ever made. It's also a fantastic heist film. Written by David Mamet and staring an awesome cast with amazing chemistry, this film twists and turns its way through the backstreets of France in a tight story that is just packed with fantastic moments. If you haven't seen this, you need to.
3. Reservoir Dogs (1992): Coming right before Pulp Fiction, this film kind of gets lost by general audiences, but it shouldn't. This is a gripping, gritty film about a simple robbery gone wrong which introduces many of the hallmarks that will become Tarantino's style, and it does so without the excesses he develops later. I highly recommend this one. It's possibly his best film.
4. The Sting (1973): This one is a classic. In fact, this is the granddaddy of all modern heist films and their good and bad traits can be drawn back to this film. And while this film unfortunately loses a lot once you know the story, this film is absolutely worth seeing, even if only to see Paul Newman, Robert Redford, and Robert Shaw at their best.
5. Ocean’s Thirteen (2007): I’m sure this is a sin, but I like this best of the three newer films and the original. This one is the most stylized and that is what works best for the setup: Danny Ocean and his crew of all-knowing hip expert criminals conspire to rob a casino owned by the venomous-yet-charismatic Al Pacino. This is great fun as an experience film if you just take it at face value and don't let reality intrude.
6. Ocean’s 11 (1960): This is a fantastic film and, as a fan of old films, this is one of the best the 1960s had to offer. Starring the Rat Pack at their peak as they conspire to take down a group of casinos all at once, this film is fun, hip and makes you wish you could have been there. That said, the film does lack the kinds of twists and turns we have come to expect from modern twist films.
7. Ocean’s Eleven (2002)/Ocean’s Twelve (2004): Between Eleven and Twelve, it's hard to say which I like better. Both have pros and both have cons. Both are equally self-indulgent and both are equally unbelievable. Still, both are very entertaining as fantasy and for the relationships between the characters. Essentially, these are buddy films in ultra-rich environments as the good guys take down arrogant villains who absolutely deserve it... kind of a feel good film.
8. Out of Sight (1998): Written by Elmore Leonard, who also wrote Justified, this film is about a US Marshal who chases a bank robber she's falling for hard. Starring George Clooney and Jennifer Lopez back when they were both top sex symbols, this is a good one.
9. A Fish Called Wanda (1988): This is the first pure comedy on the list, and it's a good one. Great characters, great dialog and a great sense of humor add this one to the list: "I looked at the clock... because I was saying to myself... It's five to seven, where could he be going with that sawed off shotgun?"
10. The Taking of Pelham One Two Three (1974): Robert Shaw is back and this time he's holding hostages in the New York subway system. This is one of those films that just works in every way and it definitely rises above the rest.
11. Kelly’s Heroes (1970): What a great idea! A group of disgruntled soldiers learns of a bank vault full of gold behind enemy lines and they decide to go get it. Before you know it, they've got half the army working with them right under the general's nose and even the Germans end up getting into the game. This is a truly fun film.