Eh, I've been an anime fan since I was 14, I still watch it to this day. But over the years of watching them, I've ran across a few that's been messed up. Well two that I can think of on the top of my head.. Those two would be
School Days
NaNa
School Days ending was fricking insane and too intense...but it has a scary sense of reality, showing what you cause a woman to do to you for using her.
NaNa...was okay in the beginning til the middle kicks in when she gets pregnant and such..then it all goes down hill.. I still haven't finished it because I was getting depressed over it.