Most Depressing/Sad Movies, Shows, Anime, etc?

Grave of the Fireflies springs to mind.

Chrono Crusade ended all sad. RahXephon was also pretty depressing in some episodes.

Hotarubi no mori e
not as sad as grave of the fireflies but it'll do the job

This has been recommended by everyone everywhere, but here it goes.

Clannad.

NO BREAKS ON THE FEEL TRAIN

Twilight. Fits perfect on your masochistic needs.

Senna

• Tokyo magnitude 8.0
  that anime will mock you in the last episode laughing at your teary face.

• Shiki

• Another

Not that saddening, but it tries to make you feel bad to the characters due to their circumstances

• Code geass series
  Up and downs, one episode you're gonna yell fuuuuuuuuuck yeah!!! then next episode you want to pull your hair out and say FUUUUUUUUUUUUUUUUUUUU

• Hanbun no Tsuki ga Noboru Sora

Very short but I recommend it.

• Mahou Shoujo Madoka Magica

Let see how maso are you right now. If you finish it without cringing, then congratz. It has a sad aspect on the story so yeah

Angel Beats. Same people as Clannad I think. Technically a happy ending, but yeah ;_;

ANOHANA , 5 centimeters per second , saddest for me was the manga of 5 cm per second though it was throughly bittersweet

Neon Genesis Evangelion is a depressing movies about a depressing boy in a depressing situation. There are currently one anime series, one anime-ending movie, and 3 out of 4 reboot movies (although the third reboot movie came out last year in Japan and will appear in US/Canadian theatres in January, so there probably aren't any discs to purchase online yet).

Edit: seems like someone already mentioned this :P

Eight Below, i cried my eyes out.
Air (anime).
The Fault In Our Stars (if you like to read).
The Girl With Glass Feet (also a book).
The Notebook (girly, but u said u wanna stay sad).
Prozac Nation (one of my fav).

Well to be honest... I have never finished watching Requiem for a Dream movie... it is too difficult and challenging for me

Moon was a pretty sad movie

Moon was a pretty sad movie

angel beats
anohana
clannad and clannad after story
tokyo magnitude 8.0

A lot of sad movies and shows and what not here.

I have a movie to trump all of them.

Old Yeller.

Enough said.

Depressing anime that I watched a while ago, Blue Gender. Well, not totally depressing. Just a lot of death.

Air (masterpiece), Ef – a tale of memories & Ef – a tale of melodies

Les Miserables

• Quite sad at the end, few other bits as well.

sleepers =(

Darker Than Black. The endings of both seasons made me shed manly tears.

tetris you live as a block that has no use other then to poof or to destroy the hopes of the person trying to make you poof

The Girl Who Leapt Through Time

Personally, even though it's a little shoujo oriented, I still think I'd say Fushigi Yuugi is worth seeing. There are some pretty fucking sad episodes in season one, but then from the last couple episodes of season one, though basically ALL of season two, it's kinda just depressing imo.
Also, there's always the last episode of Cowboy Bebop for me too. "Bang."

Edit: Oh, and movie wise, I found Requiem for a Dream to be kinda depressing too.