Somehow you made me think about a few more titles:
Weird stuff: Tetsuo: The Iron Man, a japanese sci-fi/horror movie that is difficult to place anywhere. Delicatessen is still weird, but more conventional. Cemetery Man is technically an horror, but with a unique twist and style. Plan 9 from Outer Space is considered one of worst films ever and it’s so bad that Tim Burton made a film about its author (which is instead great cinema).
Comedies: Clerks made me laugh quite a lot and it’s not even just a silly shallow movie, Juno which is more for teenagers maybe, This is the End if you are into Seth Roger’s type of hirony,
Somehow you made me think about a few more titles:
Weird stuff: Tetsuo: The Iron Man, a japanese sci-fi/horror movie that is difficult to place anywhere. Delicatessen is still weird, but more conventional. Cemetery Man is technically an horror, but with a unique twist and style. Plan 9 from Outer Space is considered one of worst films ever and it’s so bad that Tim Burton made a film about its author (which is instead great cinema).
Animation: A Scanner Darkly from the terrific Dick’s novel. For the fans of Van Gogh: Loving Vincent. Fritz the Cat, a cartoon for adults from way before it was a thing.
Comedies: Clerks made me laugh quite a lot and it’s not even just a silly shallow movie, Juno which is more for teenagers maybe, This is the End if you are into Seth Roger’s type of hirony,
With a mood: The Great Beauty is indeed beautiful, All About My Mother or anything by Almodóvar if you want to cry a bit, Lost in Translation recreates well the feeling of being out of place, A Love Song for Bobby Long an underestimated gem, or Broken Flowers.
Musical: Pink Floyd: The Wall is simply amazing. The Rocky Horror Picture Show was (still is?) a cultural phenomenon for decades.