5. Synecdoche, New York
The directorial debut of the person who wrote Being John Malkovich and Eternal Sunshine of the Spotless Mind among others, Synecdoche, New York centers on a theater director who wastes his life trying to stage a play that never gets produced and ailing from diseases which he’s convinced himself he has but really doesn’t. Like any Charlie Kaufman film, it’s delightfully meta and surreal, perhaps more so than any other film of his. Taking place on a film set modeled after New York, it breaks down the entire city only to rebuild it (literally) from scratch on-set.