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@lytning91, clockwork orange ranks as my second favorite movie ever. Yes its very very twisted, but at the heart of the movie lies the real problems with society, and people, and how some assume that we can be modified to their liking. Its not for everyone as it is very gruesome and not for the easily squeemish.
OP, besides the ones everyone has mentioned, here are some lesser known movies that will scramble your brains and leave you in awe:
Wrist cutters; a love story, The fall, Mr Nobody(I need to tell everyone to see this movie, really), sunset limited, Blade Runner, Brazil, Following, The Illusionist, being john malkovich(pretty well known, but if you havent seen it, see it), Gattaca(A recent gem I found that i dont know how I missed), Mullholand drive(the biggest mindfuck movie of all time IMO), and i could go on forever but that is a good enough start.
I try and go out and find the most bizarre, mind numbing movies made, and often it leads me to independent films which definitely hold their own against any big budget hollywood movie that tries to tingle your senses. If you ever want to know more, send me over a message, Im sure I could conjure up a few dozen more.
I would add The Man From Earth, probably throw Fight Club on there, and one of my personal favorites, Primer
If you haven’t seen Primer, I would say watch it right now, in fact, i’m going to watch it right now. The first time I saw it I watched it 2 more times within 24 hours. Easily the best movie ever made on a $7000 budget. I’ll come up with some more though
Eternal Sunshine of the Spotless Mind
Being John Malkovich
Gummo (this one will fuck with you, not necessarily in a good way)
A Beautiful Mind
The Usual Suspects
Primal Fear (my favorite)
Cube (sort of… the sequels are mind fucks, but you need to watch this for context)
Eraserhead (wtf did I just watch)
The Holy Mountain
(trailer) – http://www.youtube.com/watch?v=V_k8oaeHsnc
The Lost Highway
(trailer) – http://www.youtube.com/watch?v=1nKjO9QCSic
(trailer) – http://www.youtube.com/watch?v=nznx9Xk9zJA