One thing in life that never ceases to amuse me, even on my darkest of days, is the complete incompetence and total idiocy of so many modern criminals. I suppose we don't hear about the good ones as much, and sure, in general, good crimes are quite difficult to pull off without getting caught, but nevertheless...take the David Letterman thing for instance. The guy who was blackmailing him wanted a $2 million personal check. Did he think he could just take that to the bank? Wouldn't the average bank ask questions about a check so absurdly large? Never mind what really happened, which is that Letterman ended up going straight to the FBI, who had no trouble catching the guy, as he had given Letterman his full name (gotta make the check out to somebody for God's sake!)
Big Deal on Madonna Street is all about those people. I love that the guy orchestrating the whole plan keeps going on about the need to plan out a robbery "scientifically," and when the day comes, he can't even figure out the layout of the apartment he's standing in. This is the anti-Ocean's film, really the anti-heist film. These guys simply aren't up to the task intellectually or emotionally.
The film is rarely played outright for laughs; you don't get a lot of "look at these idiots!" moments. It's structured the same as any other heist movie - we're introduced to the players and their own reasons for needing the money, and given just enough backstory to gain our sympathy. So when things go wrong, it's equal parts heartbreaking and hilarious.