There was a somewhat similar thread here about quirky, indy films. From the list I wrote there I left out
The Brother from Another Planet which I think fits this thread. An early, low budget John Sayles effort, it's a little wobbly but finishes as a great and pleasing story.
And how about
The Big Lebowski? A Coen brothers film with cons within cons and bowling alley culture
Warning - has ample use of the "f" word