The Thomas Crown Affair (1999)

Yup, the 1999 version is the one I am singling out here. I know it is popular to say both the Pierce Brosnan and the 1968 Steve McQueen original are on equal footing, but personally I don't really like the McQueen version whatsoever. I simply have a hard time believing the hardened McQueen is some debonair millionaire. Brosnan, however, I completely believe and the light and entirely entertaining film is fantastic. From the clever ways Crown goes about stealing the paintings, the cat and mouse game and the tongue-in-cheek humor always manage to entertain me. Yeah, the logic is a bit silly, but that doesn't stop it from being fun.

The Asphalt Jungle

Aside from the fact that it has a small role for Marilyn Monroe, The Asphalt Jungle is worthy of this list primarily for the cast of characters it places front and center. Primarily the likable hooligan Dix Handley played by Sterling Hayden and the mastermind behind the whole thing Doc Riedenschneider played by Sam Jaffe. The heist isn't the most exciting and action packed heist on this list, but the double cross and the back-story for each character add plenty to the plot to keep you intrigued. Also, the old school gangster-style dialogue adds to the intrigue.

Thief

Here we have one of Michael Mann's first feature films and it stars James Caan as Frank, a professional thief that has caught the attention of a local gangster with the inside scoop on some major scores. After Frank agrees to a couple of jobs for the gangster he realizes he may be in way over his head. A great heist in the middle of a personal drama and a satisfying level of violence makes this a worthy entry.

The Killing

It shouldn't come as any kind of surprise that Stanley Kubrick has himself a heist film, the guy has a film in pretty much every single genre, why not take a stab at one of the harder ones? The Killing is definitely not Kubrick's best work, but it is the $2 million racetrack robbery devised in the film that makes up for the rather shaky and obvious plot, which is primarily saddled by the narration, which I am not sure was entirely necessary. This is probably Kubrick's most obvious film in terms of what is going to happen, but it's the execution of the heist that saves it. This film also marks Sterling Hayden's second appearance on the list.

The Italian Job (2003)

I have never seen the 1969 original The Italian Job and while I have heard it is quite good, the same people that tell me that also tell me this 2003 remake is just as good, if not better. Personally, I love, this film. I love the greed, love and revenge the plot relies on to move the story forward. The best part is that the love story comes as a result of the story and is actually far more believable than the typical cliché romance that springs up out of unconventional movie situations. Oh, and Charlize look gorgeous in this flick, that always counts for something.

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