I feel kinda messed up cause I like most of the movies mentioned in this thread. The Big Lebowski, Taxi Driver, A Clockwork Orange, Plan 9. But I'm pretty sure that they were just messed up in a good way.
À ma soeur! (AKA Fat Girl)
The ending is the most surprising and shocking I might have ever seen.
Compared to other movies mentioned in this thread, this film isn't just nuts from the beginning to the end but it feels real which makes it really strange experience.
After you have seen it, you add it into "messed up"-list in no time.
I would add Sitcom by Francois Ozon to messed up movies; eXistenZ by Cronenberg; Mullholland Drive and Dune (well... anything by Lynch) can imo also be added to that list.
concerning Crap SciFi: Anyone knows Zardoz with Sean Connery from 1974
Yeah, Zardoz is pretty freaky. Also try David Lynch's Eraserhead or Tsukamoto Shinya's Tetsuo: The Iron Man.
edit: didn't notice that Blonde already mentioned Lynch, but Eraserhead has to be the most freaky, not counting the early short films.
Also, Happiness of the Katakuris was mentioned; it's weird but harmless, while Audition and Visitor Q from the same director were much more "messed up."
If the intent is "bad", my vote goes to Mazes and Monsters, with a dishonorable mention to Robot Jox. There was one movie even worse which I saw, but my mind has purged all memory of it, probably in self-defense. All I can remember is standing up in the theater afterwards yelling "I want my money back! I want everybody's money back!"
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