[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.

[Oni]

I didn't really think Bebop's was all that miserable. I think the two most depressing I've seen were Anohana and Grave of the Fireflies. We streamed Grave of the Fireflies and I'm pretty sure everyone wanted to kill themselves after.

Spoiler:

Some people, including myself, theorize Spike (from Cowboy Bebop) lived.

[Jiggly]

I didn't really think Bebop's was all that miserable. I think the two most depressing I've seen were Anohana and Grave of the Fireflies. We streamed Grave of the Fireflies and I'm pretty sure everyone wanted to kill themselves after.

Spoiler:

Some people, including myself, theorize Spike (from Cowboy Bebop) lived.

I didn't think it was that bad either.

Spoiler:

Although, I was sad when the team broke up XD