I don't even remember but the last movie I legit BAWLED and cried myself to sleep over was Prayers For Bobby I watched it a few days ago and I suggest all the gays watch it be be warned you WILL cry
The story of Marcus and Jason is so incredibly sad in Hereafter. I just watched this little fanmade Youtube video, and I cried at the last bit. I'm seriously gonna watch this movie again soon!
OMGGGG.
The way Marcus grabs Jason's hat at the enddd. OMGGGG.
If they wouldn't have put that ****ing music in the video, I would still be crying.
I remembered I rented it late night when we were visiting Las Vegas in 2002: Spirit: Stallion of the Cimarron.
I don't remember the exact moment, but I believe it was when the Native American let Spirit go, and the girl horse Spirit was with ran with him, or something.
That whole moment caught me off-guard, and since it was late night and I was super tired, the tears just started rolling. Never again, though. I watch that movie, and it's just a touching moment, nothing more. I probably have to be either super tired again, or super drunk...
I almost cried. I also balled my eyes out randomly when I was 8 during a Pokemon episode.
As for movies, I've only cried watching Crash and Lost in Translation. Those weren't even the first times I watched them, I was just an emotional wreck.
Oh, and I cried at the end of The Dark Knight Rises
it's really heartbreaking 
