Alright here is one to start talking about. Which anime or show has you have watch with a sad ending so hard that it sometimes makes it hard for you to watch again. 
January 30, 2013 - 8:57pm
#1
Sad ending makes it too hard to watch
Newsletter Signup
Berserk, the ending of that was brutal and tore me apart as after watching the progression from start to then was amazing. It didn't make it hard for me to watch the series again per se but it really hit me the first time i saw it.
Another was 5 Centimeters per second. I'm not normally bother about films like that typically but at the end you almost can't help but feel sad.
Figure collection / Fan Art / Deviant Art
Anohana....I could only make it to 5 episodes and could see where it was heading. Just couldn't finish it.
Sponges grow in the ocean. That just kills me. I wonder how much deeper the ocean would be if that didn’t happen.- Steven Wright
Couple things:
For anime endings that are tough for me to deal with, and don't laugh; Chobits, it leaves me with a massive emotional hangover after finishing it, it reminds me a lot of that Steven Spielberg movie A.I.
As for other endings I despise, let's see, well, anything that has a big build up or cliffhanger - pretty much a blatant setup for a sequel season/movie/OVA and nothing comes out.
The guilty parties for this crime include but aren't limited too:
Freezing
Sekirei
Mermaid Forest
Tenjho Tenge
Spice & Wolf
Highschool of the Dead
That's all I can think of right now.
I have to go with Air.
"When you truly care about someone, you don't need any specific reasons to justify your feelings. If you don't know why you feel the way you do, then you can't lose that which causes you to care."
Phantom and Clannad: After Story have two of the saddest ending I have ever seen; anime or not.
RLTW
Clannad, angel beats and elfin lied
POG life
Just rented Seven Psychopaths...that whole movie is kind of depressing, I thought it was more of a comedy...but its really not...theres funny moments..but yea...its a fairly depressing/bittersweet flick.
Isn't It Great To Different, Isn't It Great To Be Who You Are!? Once You Learn To Accept Yourself, You'll Become A Shining Star.