Hard to choose, but the first ones I ever saw were Match Point and Anything Else. Anything Else was offbeat (Christina Ricci) while Match Point was both commercial and sophisticated at the same time. Top Five, for sure.
I had a Woody Allen-watching binge in 2015, who knows I may have seen ten of his films in one year. The most arthouse of them, reportedly modeled after Ingmar Bergman, is Interiors. If you like capital F Film, you must watch this. If you can't stand sad reality, then avoid. Woody Allen has a few oft-repeated themes, one of them is what conservative people might tag marriage-bashing. See Husbands and Wives to continue the education. What's New Pussycat? to see Peter O'Toole join the fun. It's a very old film and took me several tries to stop falling asleep. Hollywood Ending if you want to see true love win in the end - no, you won't fall asleep.
Before the binge, I saw and loved Midnight in Paris. Then the binge gave me two related experiences that I love just as much: Magic in the Moonlight + The Purple Rose of Cairo. Mmua, all three of them. Mmua.
My binge started with finally getting to the end of Vicky Cristina Barcelona. It's an interesting film because, this guy knows how to romance places - Barcelona in this case, because he knows what to do with Scarlett Johansson (or ScarJo just plain always knows what to do; be good, bad, dangerous, imperfect, and alluring on film), because Javier Bardem looks the way he does, because Penelope Cruz sounds the way she does, and because it's generally not alright in real life to share romance in the way this movie depicts.
I think I've seen Whatever Works in a theater, though I'm fuzzy on details like Anything Else. They must have been alike, with a very good lead actor playing a very jaded or rebellious character that makes untraditional choices for their sexual relationship(s). I almost forgot about Manhattan. It must have been like Husbands and Wives, but with less drama. A Russian student had his (Woody's) attention, I think. Love and Death had more colour and more Russian and more explicit humour; a very theatrical experience, even if the story line evades me.
To Rome With Love I think I saw without subtitles - oops. I ditched Take The Money and Run because it seemed super-stupid; not my genre. The critics always say Annie Hall is his greatest, guess I'll have to watch that again. It seemed funny, quirky, and romance-y enough.
Next, I'm going to see Fading Gigolo (I hear it's boring, un sympathique petit film as someone called it - which is often my thing), and New York Stories (I hope he's in his element in his city.) Then maybe Play It Again, Sam and Paris-Manhattan will be next?
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