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For my partner and I, it'd surely have to be Baskin. I'm actually surprised to see a thread like this without it.
They're Inside comes to mind next, but for more story reasons than just the freaky goings on.
I've watched Baskin and I dunno, it's fucked up for sure.. But I feel like I've watched way much worse (as in fucked up) movies.
Depends on your horror tastes, of course. We have no interest in Martyrs or A Serbian Film type stuff even if Baskin was pretty redeemable on general weirdness, and we all know there's plenty worse than any of those out there.
Maybe most people who watch Baskin tend to venture even further out, but it seems like a notable watershed point to me.
Unfortunately I've seen both of the mentioned movies.