After seeing the semi-pallid Ocean's Thirteen (okay, the guys looked pretty good), we got into a discussion of the best heist movies ever. Which movies stand out in your mind? For instance, someone said Dog Day Afternoon, but would that really count? Should a heist movie be mostly about planning and executing a heist and not sidebar into other issues.

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My vote goes, without hesitation, to a little B picture made in 1957 called Plunder Road, starring Gene Raymond. It's a flawlessly-executed story of a gold heist. It's never on TV, so I recommend searching the video sites for it. It's well worth the effort.
Well I am an unabashed fan of Michael Mann, so I would say Thief is his best heist flick, but Heat is a sweeping masterpiece of criminal trade craft (Interestingly he had a former British special operations NCO consult on everything from ambushes, like the infamous bank/street gunbattle, to B&E techniques, via the 'hard key' at the precious metals facility)

I would throw John Boorman's The General in there as well (an uneven movie, but some interesting heists sprinkled throughout and ultimately saved by Brendon Gleason.)
What about "The Day of the Jackal", whilst not a heist movie per se it shares some of the similarities of the genre in the sense that it is all about the planning and attempted execution of a crime.

Also I loved the movie "Face" starring Ray Winstone and Robert Carlyle. It is a British crime movie and had, if I remember rightly, an excellent heist planned and executed.
I second The Day of the Jackal, but the original, not the remake.
Nice to see a mention of my favorite, Big Deal on Madonna Street. That's a rare example of a spoof that is arguably better than the movies at which it pokes fun.

Westlake loved the movie, and he was a man of taste as well as accomplishment.
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John Travolta in 'Face/off', and for a little heist comic relief 'A Fish Called Wanda', AND 'Entrapment' (Sean is like bottle of Grange, ages well, and remember to lay flat in a dark place, preferably with me) LOL.....
Heat
The Town
The Italian Job (the original)
Inside Man
Le Circ de Rouge
The Taking Of Pelam 123 (the original)
Charlie Varrick
Thomas Crown Affair (the original)
Reservoir Dogs
Foolproof
The Italian Job (remake 2003)
Ocean's 11 (remake)
The Lookout
The Getaway

Just to name the ones that came to me first.
I may have missed it why it wouldn't qualify but--I loved The Sting! 
I'm surprised no one mentioned THE STING with Newman and Redford.

 

My twisted additions:

 

Killing Zoe

 

Sexy Beast

Sexy Beast. Yeah. Loved it. What an opening shot! I still remember it and I saw it ages ago.

 

Plus, Ben Kingsley was incredible.

Indeed! The actual heist scene was incredible, also.

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