1) Synecdoche, New York
So you think you have serious ambitions? How about aspiring to tell the story of all of humankind in a single stage production? Charlie Kaufman made a name for himself by bringing the weirdness of Being John Malkovich and Adaptation into being (with the help of Spike Jonze), but when given complete control as director, his weirdness comes unbridled and the result is Synecdoche, New York.
Kaufman was Inceptioning audiences years before Inception even came out. Adaptation offered a dizzying story of a screenwriter named Charlie Kaufman who writes himself into his own movie. Synecdoche takes this even further, with a theater director, Caden, directing a play about his life directing a play about his life directing a play about his life, and so on. But it also contains some of the most melancholy reflections on life’s futility, our unsatisfying and unsatisfiable quest for meaning and purpose, and the inability to truly connect with other people.
Caden is obsessed with death, and it’s this obsession that spurs his ambitious project, which is completely in vain. It’s a movie with incredible insight that is so specific and yet, if you’re able to get onto its frequency, speaks to some universal experience that is simultaneously sad and joyous. One of the best things about this movie is that there’s no added pressure for you to “get it” when you watch it, because I’m pretty sure no one truly gets it. Like life, I guess? I don’t know of another film that describes life more accurately than this one.