I resent that you don't have even one Woody Allen's movie in your top list. In mine there would be at least 5 of them :). This might be a shocker, but I've never watched one all the way through. OK, I'll ask....which is the best to watch?
Here's a movie that I wish had been made, but never was. Author James Kirkwood (who co-wrote "A Chorus Line" with Nicholas Dante) wrote a great novel called "Good Times, Bad Times". It's a bit like Catcher in the Rye, though (in my opinion) a bit more clever. It would have been a fantastic movie.
Here's the book:
http://www.amazon.com/Good-Times-Bad-James-Kirkwood/dp/0449204693