[Jiggly]

Some time ago, we ran a stream for Grave of the Fireflies, and not to give any spoilers - but came away feeling so depressed and heavily regretted our choice in stream material for the night.

AnimeNewsNewtork posted a poll here.
In the link above it lists the top 21 anime with the most miserable endings.

Some other well-known shows in the line-up:

• Fullmetal Alchemist
  
• School Days
  
• Death Note
  
• Cowboy Bebop
  
• Fate/Zero
  

I was surprised not to see Anohana: The Flower We Saw That Day in the list. Genuinely cried.