#62 Annie Hall: I was a lot more attractive when the evening began.

1977. dir. Woody Allen, starring Woody Allen, Diane Keaton.

Seen it before? Yes.

Marge Simpson: Did anyone see the new Woodsy Allen movie?
Ned Flanders: You know, I like his films except for that nervous fellow that's always in 'em.

The Simpsons, A Milhouse Divided

Woody Allen plays Alvy Singer, the most neurotic movie character ever. He constantly whines about everything. Seriously, this guy, you just want to punch him in the face. The movie consists of him, at length and from many perspectives, analyzing his failed relationship with the titular Annie Hall (Diane Keaton). The movie uses a lot of creative storytelling devices:

• Alvy steps into the past to explore his formative experiences. The funniest of these scenes is when he goes back to elementary school.
• Alvy and Annie have a conversation, with subtitles revealing the subtext of what they're saying.
• Split screens, where the two halves are ironic counterparts to each other.
• Alvy is irritated with a loudmouth talkinga bout Marshall MacLuhan, so he shuts him up by having Marshall MacLuhan refute him.
• Annie is bored during sex, and her spirit gets up and walks away while her body remains.
• Alvy strikes up conversations with total strangers, who are all weirdly honest with him.

It's a very clever movie, and it's as much about Alvy's relationship with New York and his struggles within himself as it is about his relationship with Annie. It's funny, but there are a lot of references to late 70's pop culture that don't really fly anymore. Also what the hell was up with Diane Keaton's wardrobe in this movie? I read that this caused a fashion sensation back in '77; what were people thinking? She looks like a mental patient.

Position on the list: 132
Hey! It's that guy!: A lot of them... Paul Simon, Sigourney Weaver, Jeff Goldblum, Truman Capote, among others.