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Try any movie in the Mystery Science Theater 3000 show some of those movies are messed up. Like The Last Sacrifice, Manos: Hands of Fate, and a whole bunch of others
wrist-cutters a love story
This might have been said before but I'll say it anyway Hausu(House) it's a japanese horror comedy kind on the level of Evil Dead and Beetlejuice.

Unaware that evil spirits have taken over her invalid aunt's isolated country house, Oshare (Kimiko Ikegami) and six schoolgirl friends arrive for a visit -- only to face a slew of preposterously freaky events in Nobuhiko Obayashi's 1977 psychedelic nightmare. As the girls begin vanishing one by one, the survivors encounter ravenous furniture, homicidal firewood, a possessed piano and other absurd and violent entities.

Puppet master 1-3. thats the series of killer puppets. its a B-movie but its the best. allot of people love it! theres 1-10 movies. PM 9 is By Si-Fi which was gay. but its a good movie. theres a Few WTF? parts. The weirdest one is PM1.
You should see Brazil. It's surreal and hilarious, and so what, obvious social commentary is obvious? It's still an amazing film. I highly, highly recommend it.
Peter Jackson's 'heavenly creatures' was a movie about two lesbos you might wanna spare a watch

no i didnt like i just found it weird that fit what you asking
The matrix?
Mr Nobody
The Keep is a very strange movie, its about Nazis that Wake a thousands of years old jewish vampire that shoots lazer beams. Soundtrack is done by Tangerine dream who are amazing.

Here's a trailer.

The Holy Mountain is a strange film too but even more strange than anything else.
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Toothsome Gekko

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I'm 10 pages in, so sorry if someone already mentioned this, but...
Tokyo Gore Police? Don't be turned down by the stupid generic name. It was actually really
funny, perverted in a strange anime way and EXTREMELY ******** up. Some kicks involve a girl chained as a dog slave, a man's d**k who gets chopped(actually bitten off) and turns into a cannon and so forth in that pleasant fashion.
Any one of the saws or hostels

Mind blown in the worse way possible biggrin
Anything by David Lynch. He's done a lot with his career that revolves around the mysterious/obscure. Blue Velvet, The Dune, Fire Walk With Me, Twin Peaks- they're all great suggestions.
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I love this move so much

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