(Just a single rule: mix-tape-style, no more than one film per director. You know, because otherwise the whole thing would be pointless.)
(#5) Annie Hall
Romantic Comedy • dir. Woody Allen • 1977 • USA
Before I was even born (1981), Woody Allen had already written and directed 10 movies, and enjoyed a couple of hits on Broadway. Before that he made a huge splash as a stand-up comedian. And before that he wrote gags for some of TV’s biggest names, including Sid Ceasar, Ed Sullivan, Jack Paar, and Johnny Carson. Through it all, he also found the time to write dozens of short stories for The New Yorker, all of which, collected into anthologies, are still in print and available today. In my lifetime, he’s continued to be every bit as prolific: 33 more films, and counting. (Of course, more often than not, he stars in them as well.) And, yes, somewhere in his beloved New York, he plays clarinet in his own jazz band every Monday.
Now that, my friends, is what you call a career. (Boy, sometimes just clearing a bunch of crap off my desk feels like a decent day’s work.) At a rough count I’ve seen 30 of Allen’s films, and the ones I like best several times each. I’ve enjoyed them all, even Hollywood Ending. A dozen at least are among my favorite movies period. You know what, though? If Woody Allen had made Annie Hall and precisely nothing else, he would still loom large in the history of comedy and cinema. It’s got Diane Keaton at her charming, effervescent best. An amazing Christopher Walken cameo, long before that was even a thing. Woody in Los Angeles, deliciously ill-equipped to drive and reacting anxiously to everything in sight. That lobster scene – as fun, fresh and unaffected as filmmaking ever gets. And it just nails falling in love, first dates, growing apart, and breaking up. See, and I haven’t even mentioned yet the beautiful Gordon Willis cinematography… Or, “Yeah, I know; and such small portions…” “Those who can’t teach, teach gym…” “In the event of war, I’m a hostage…” “La-di-da…” Annie Hall is that rarest of things: perfect.