This is a classic Woody Allen film, complete with all the classic Woody Allen hallmarks, and, you know what? I actually had to watch it twice because upon completion of one viewing, I was actually stunned and unable to really decide how I felt about the film. That sort of thing almost never happens, either. It was weird. I watched it, and truly was unable to decide how I felt. I didn't love it, but I didn't hate it. So, I gave it another watch, and any sort of issues I had with this film (it mostly has to do with the unlikeability and unsympatheticness of the characters) kinda worked themselves out on the second viewing.
I actually like that the characters, especially Woody's are rather slimy, creepy jerks. It adds to the fun and nuttiness of it all. That, and it takes real talent to successfully pull off a dramedy where a twice divorced 42 year-old is dating a 17 year-old girl whom he doesn't love, despite the strong feelings she has for him. Plus, there's lots of typical pretentious conversations about art, music, and philosophy that just really sing. Also, this was the first time Allen made not only a black and white film, but one that was also visually stunning, something that doesn't apply to the vast majority of his works.
This is a true love letter to Manhattan, and the gorgeous cinematography, excellent Gershwin score, and Allen's crisp writing make it truly the masterpiece that everyone hails it to be, and I think this film really truly does stand the test of time since I was forced to give it multiple watches and lots of thought before deciding how I really felt about it. Now THAT's a sign of genius.