That's a great start (minus Woody Allen - I have hated all of his movies that I've watched of his).
Might do some research into which movies might have decent behind the scenes or director's commentaries too.
Want to mix in some silly stuff too. Comedies/horror/cheesy action, etc.. If I do all classics I won't last very long.
I'd add Wim Wenders, Egoyan, Bergman didn't make that list (!?!), Herzog, Welles off the top of my head. (eta: and of course Malick)re: Woody Allen- Have you seen Annie Hall, Crimes and Misdemeanors, Broadway Danny Rose or Sleeper? I feel like he's been
repeating himself for a while now and have basically stopped watching his movies, but the ones I just listed, and a lot of what he was doing in the 70s and early 80s is very worthy of watching/discussing.