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NHK was pretty depressing in many ways. Great though

Fullmetal Alchemist takes the cake. I cried nearly every single episode. Chrno Crusade also had me sobbing, but the manga had more of an emotional impact on me.

Grave of the Fireflies (like everybody else)
Pale Cocoon

NHK could have made my list if the end went differently.

Saikano
Chrono Crusade
Lain (depressing)
Elfen Lied
Full Moon wo Sagashite
BLOOD+
Fullmetal Alchemist

How about Death Note I was really hopeing Light would win in the end.

Air TV and Chrono Crusade, I couldn't stop crying and still if I think back at it it's like I'm gonna cry

Saikano
Air
Wolf's Rain

Tengen Toppa Gurren-Lagann Episode 8...
:'(

Kanon 2006
Higurashi no Naku Koro ni
Red Garden (I'm only on ep 5 but it has its moments)

And I can see how School Days is depressing. The human relationships in it are portrayed more realistically than in most anime series.

Sure
[SARCASM]
[/SARCASM]

Chrno Crusade
Grave of the Fireflies
Wolf's Rain
Full Metal Alchemist

Chrno Crusade & Wolf' Rain definitly had me near tears

ahhh the last episode of azumanga daioh got me tearing cause its my last year in hs too *tear*

Then I fear what will become of this world if girls are stupid enough to throw themselves on a single guy who's as worthless as trash.

Air TV is really depressing... especially the ending. It left such an empty feeling. ;_;

I didn't say all of it was. It's just not a fairy tale romance type of anime, where everything works out well in the end. it's a pretty typical life situation. A guy tries to hook up with lots of girls, cheats, lies and everyone's getting hurt in the process.

I honestly can't remember not crying during any episode of Haibane-Renmei.

Saikano and Welcome to the NHK (for some reason) are the ones that depressed me the most while watching.

GURREN LAGANN.
that shit makes me cry every week :'(

ive never watched an anime that made me sad/depressed :\ is that bad? :|

I cried at a few anime, but I think I cried the most while watching the last episodes of Air. My tears just didn't stop, I couldn't even see the subs T_T

But the most depressing one was Serial Experiments Lain. I'm a really posotive person but just had to shout out the world for 2 days after that ^^'

If you've never been emotionally moved by a piece of fiction, you're missing out :(