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Most messed up/Disturbing Movie You Ever Saw?

How so? I liked the movie and can’t find anything disturbing or messed up about it.

Kind of a private joke for me. It's a 1,000% "chick flick". I saw it in the theater back then with my girlfriend at the time and her best friend at the time (female). They bonded so strongly during it that they nearly conjoined. That best friend of hers convinced her to move away to live with her in a different state so they could stay "Besties" and my girlfriend agreed. So it's for personal reasons that I didn't like the film. Blossom was good in it though.
 
I recommend checking out The Sadness if one wants to watch one of the most depraved movies ever produced.
 
There's a black and white French film about a group that bets of Russian Roulette with poor people playing.
I can't remember the name.
The main character is doing it to get money for his sister's medicine.

Watched Full Metal Jacket and Apocalypse Now 2 days before going to Basic Combat Training.
Full Metal Jacket actually helped I think.

The film is named 13 (Haven't seen it).

I dislike horror films and have always been really sensitive to blood and gore, so I try to avoid them as best I can (no problem with horror novels). There were some scary movies I didn't manage to avoid as a kid though.

The first one is Spirited Away (like a lot of people here mention. Saw it when I was 5 first but am very glad I watched it again many years later).

Tekkonkinkreet (Black or White). It's an anime movie about two brothers which is pretty messed up psychologically. A friend who is really into anime basically forced me to watch it when I was 10-11. I'm sure it wouldn't be as bad now, but it deeply affected me and I had nightmares about it.

In Danish class, we were for some reason meant to watch a Danish claymation movie. The Danish are known for having absolutely pitch black humor, and in one of the scenes, the kids are watching a horror movie where a chainsaw murderer (bloodily) splits someone's head open (the film also cuts straight to a close up of that). I was 15 then, but still really didn't like it. I have no idea what the name of it is, but I doubt there are many Danish claymation films.
 
I can't say definitively which movie is the most disturbing I've seen. but The House That Jack Built was the most psychologically screwed-up one I've seen in a while. Tetsuo: The Iron Man is the grossest, and The Road is the flat-out bleakest and most depressing movie of any I've ever watched. I also found Whiplash pretty disturbing but not for the same reasons as a horror or slasher or post-apocalypse movie.
 
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The Human Centipede is hands down the most disturbing film ive ever seen, actually number 2 is way worse.

I don't recommend them, they are highly disturbing, and have no idea what would posses someone to create such a crazy idea for a movie.
 
A few of those old PSAs that teachers used to show kids in class are really messed up especially the one that basically promotes homophobia by claiming all adult gay men are trying to seduce boys for sex to the one where everyone calls a girl a huge “snob” just because she isn’t into going to parties and wants to study hard and get good grades to better herself. The latter is particularly awful if you watch it without any riffing (it is a popular PSA for riff videos) as all the other characters guilt trip the girl and gaslight her into thinking she was a “snob” and should be ashamed of herself just because she just wants to study and get good grades because she’s a girl. Even her mom is guilty of the gaslighting. Sure, Mom, you tell you daughter that “having a good time” is more important than getting good grades. You’ll have no one else to blame once the grades start plummeting and your daughter is out walking the streets at night picking up lonely businessmen in town for a job assignment.
 
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