Which Woody would he start with?
I think Manhattan is a beautiful film as well, but I agree with magstheaxe in that it just feels a little too self-indulgent, even for Woody Allen. Annie Hall is a wonderful film and really does define his entire serious style. He can veer from surreal hilarity to soul-crushingly depressing really damn quickly, and I think this is why the film still works, no matter how dated it looks. As characters, Annie and Alvy (and their relationship which is a character of its own) are the, er, realest people Allen has ever written. Sleeper is his amazingly goofy take on Buster Keaton silent comedy (while not exactly being silent) and I still laugh like a loon no matter how many times I’ve seen it. Sweet and Lowdown gets amazing performances out of Sean Penn and Samantha Morton (who doesn’t say a single word of dialogue in the film) and I think it’s a wonderfully bittersweet film. Another film I’ll throw out here, even though Allen did not direct it, is
