(By plan I mean any movie where people make a plan to do something and carry it out wether it be a robbery or a murder or a military operation,escape from prison etcetera)
The common favourite Heist-wise is The Italian Job (original version)or Reservoir Dogs although I really like The First Great Train Robbery with Sean Connery and Donald Sutherland or The League Of Gentlemen (1959)with Jack Hawkins.
The Thomas Crown Affair is good (Brosnan's version is v. cool) Thief - Brilliant soundtrack Ronin Entrapment - yes I know it OTT but still it ain't a bad film!
"My father had a profound influence on me. He was a lunatic" *Meet the new boss...Same as the old boss*
The Sting. Paul Newman is so swoonsome in that and it's a brilliant film. I love to get the video out every now and then when I've got nothing better to do. It wtill knocks me out. And the Scott Joplin soundtrack is pretty stunning too.
Without question it's Asphalt Jungle. A perfect film on every level. then maybe Rififi or Dog Day Afternoon or Reservoir Dogs or the Taking of Pelham 123, The League of Gentlemen is ace and of course The Usual Suspects. I love heist/caper movies actually, its maybe my favorite of all the sub genres. I also like The First Great Train Robbery and The Anderson Tapes, both with Sean Connery