I think you have to be a 4th generation New York Jew to get Mr Allen completely. Being a lapsed catholic myself helps a lot with the angst/guilt side of it but a lot of it must go over the top of my head
I think
Hannah and her Sisters is about the most 'accessible' of his movies but
Annie Hall's not too weird and is the most iconic of his early career (pre Mia Farrow).
I do like
Play it again Sam as well but I adore Bogart movies so that helped of course.
Mama Mia -
great corny movie and I bawled my eyes when Meryl sang
Winner takes it all!