Lily and Jim

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This one's right behind World of Tomorrow in my best-of-Don Hertzfeldt-list! Lily and Jim is more nuanced and funny than most full feature romantic comedies. It's about the assumptions we make about other people, especially potential partners in a romantic relationship and being afraid of each other because of personal shortcomings. Lily and Jim is a cautionary tale promoting honesty and courage, packed into crudely drawn 13 minutes.