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I'll have to agree with snowy and say The Machinist. I own it, and still watch it every now and then, but I always get kind of depressed afterward.
Gummo. That movie is just too depressing all the way through, like The Machinist, but completely different...
Leaving Las Vegas. Even though I knew what was going to happen less than halfway through, I still wasn't ready for it when it did actually happen.
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