The Asphalt Jungle (1950) dir. John Huston
The real fun heist movies are the ones that let you think "I could do that." You can look around at your friends and pick out which one would be the heavy, which the safecracker, and which the master planner (me). And of course, which the double-crosser.
Everyone in The Asphalt Jungle is a real person. Nobody can hack into a traffic light using a cell phone, or win a rice rocket in a street race. At least, nobody I know.
Even Asphalt's genius, Doc Riedenschneider, overestimates his own capabilities.
Several critics credit Asphalt as the first real heist movie, where the criminals are the protagonists.   It certainly set the template. 60 years later, the only real deviation from the Backstory-Idea-Plot-Everything-Goes-Wrong-I-Thought-I-Could-Trust-You plot is how things end up. But of course, The Asphalt Jungle was working in the Code-fueled Noir era.
The Asphalt Jungle is #288 on the 2011 edition of the TSPDT 1,000 list I’m blogging through. I’ve now seen 420.