I can't remember the last time I actually cried, but here are some things that get me close:
When Alex inquires about his snake in A Clockwork Orange. The first time I watched it the line MY SNAKE, WHERE'S MY SNAKE hit me hard man.
The ending of Mulholland Dr. and, upon further reflection, the whole fucking thing. This concept of unrequited love/borderline obsession gets to me I think? Also Diane's life fucking sucks, IT CAN BE ARGUED that she was sexually molested by her grandparents or parents which is part of what lead to this obsession with Camilla BLAH BLAH BLAH im probably shouldn't go into another essay on mulholland drive right now maybe later.
Basically all of The Elephant Man. I think there was a particular line that got to me but I can't remember it off the top of my head, I'll get back to you guys on that one.
Also that episode of Futurama where Fry tries to revive his dog. It didn't really almost make me cry but it did get to me in some way.
edit: also elliott smith all day basically