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[tuffy]

Although much of Texhnolyze plays out like a futuristic gangster series, it culminates in the most depressing ending I can think of.

 

[Palmer_v1]

Grave of the Fireflies... which in 50 posts, has probably been listed 46 times.

This might sound odd, but I found The Girl Who Leapt Through Time very sad.

I found it very bittersweet as well.

Bridge to Terabithia

Movie/book was created for the sole purpose of making children bawl.

 

[Takamura-San]

Samurai X: Trust & Betrayal - You'll love the OST too.

Only right answer.

 

[meltingparappa]

Wolf Children front loads unimaginable sadness.

Summer Wars (same director) got me pretty misty too, actually.

 

[John Kowalski]

A lot of good recommendations so far, but i feel like i should reinforce some suggestions.

Shinkai movies (5 centimeters, Voices form a Distant Star, etc.) aren't depressing so much as they give you that feeling of having to cry to move on from what you just experienced while the movie is still going. May not be what you're looking for, but maybe it is.

Now and There, Here and There is outright shocking and unrelenting, and likelier to leave you depressed for a long period of time while you adapt to the fact that the things that make it so disgusting at times are stuff that happen every day irl.

Colorful (WHICH I HIGHLY RECOMMEND) is the likeliest to make you cry because of your own personal stuff, which is the kind of thing that really gets me BUT maybe that's not your thing.

Shindler's List has what is likely to be one of the saddest scenes in cinema ever, so maybe just put that in repeat on youtube until you break.

I remember Koi Kaze being very harsh on my mind way back when, even the upbeat ending left me in an even worse state.

 

[daveo42]

My girlfriend showed me that a couple months ago, didnt make me cry, it may have been because she hyped it up to be sad?

You have no soul.

I'd say Bokurano, but it's really depressing too and is one of my favorite mech animes ever. Not nearly as depressing as End of Eva, but pretty close. There's another one that's really sad and depressing too called Saikano, about a girl who ends up becoming a weapon of ultimate destruction to try and save the world.

Try these if you need a good cry and some self reflection. I apologize, since I can't think of any good, sad movie for you OP. Saikano is shorter at 13 episodes. I'd say you could always read the manga for both, which are superior.

Bridge to Terabithia

Fuck this movie and the way it made me bawl like a little kid at the movie theater.

 

[Koppai]

Grave of the Fireflies

Came to post this!!!

Hachi: A Dog's Tale

 

[BadWolf]

Out of the more recent one's, Wolf Children really hit the spot.

 

[Witchfinder General]

Tokyo Godfathers

 

[theechrisfox]

Kids

 

[daveo42]

Not a movie or anime but a thread here on GAF:

http://neogaf.com/forum/showthread.php?t=507587


If this doesn't make you cry nothing will...

From that thread:

Yeah, videos with feels are cool too. I need to add that to OP.

Spider-Man feels:

Fuck man...

 

[CadetMahoney]

Royal Space Force: The Wings of Honnêamise

http://en.wikipedia.org/wiki/Royal_Space_Force:_The_Wings_of_Honnêamise

Not that sad, but not upbeat either.

 

[Platy]

Dancer in The Dark
Toy Story 3

also
Requiem for a Dream
but not sure if the right kind of sad


... and maybe every non kiddy dog movie =P
Marley, Hachi and things like that

edit :
Also, the first 10 minutes of UP

 

[MikeHattsu]

From that thread:

Fuck man...

Ack... Why did I read that. I'm still at work...

 

[Platy]

Harvie Krumpet and Mary & Max (an animated feature by the same dude) are also awesome sad pieces of video