The most depressing movies you've seen

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falling down has some very sad and depressing parts (not least, the ending) but the insanity storyline and the really screwed up humour off set it nicely ^.^

i thought the end of "blow" was a bit of a downer.

oh, and i actually cried at the end of AI

<p**** XD

oh yeah, Leaving Las Vegas is definately high up on my depressive list as well.

"Hancock"

High School Musical and The Sound of Music. Ugh.

Anything based on history where you know the outcome will be cataclysmic and you can't rewrite it -- e.g. JFK, Titanic, Malcolm X, The Passion of the Christ.

Well, I...er, that is to say, I...crap! For some reason I'm having trouble with this! I can think of TV shows that have had depressing endings (last season of House), video games with serious "downer" conclusions (Silent Hill 2), and even a play that's pretty damn depressing (The Glass Menagerie). But for some freakin' reason, I'm having trouble pinpointing a movie that I found particularly depressing.

Schindler's List, I guess...maybe No Country for Old Men (though it's more thought-provoking than depressing). Night of the Living Dead...no, I wouldn't call that one depressing so much as gruesome and horrifying. Well, I thought of two. Or one and a half. That's good enough.

"Grave of the fireflies", I have never felt so depressed. Some people think animated movies can not be touching, but they really can.

The boy in the striped pyjamas is another one, but is not that depressing overall.

Pan's Labyrinth was grim for me.

I cried when I saw Forrest Gump on TV, in a weird way I saw some of myself in it.

The Mist
May-All the character wanted was acceptance and friendship, but she couldn't get it because she was different. So, she, out of desperation, decides to make a friend out of assorted human body parts. At the end, just when her perfect friend will finally be complete, she sacrifices herself to complete her new friend. So, what I find depressing is, she's just about to achieve her goal and get what she wanted all along, but she doesn't achieve her dream and basically spent her entire life alone. Maybe I find this movie depressing because I see similarities between myself and May, the main character.
Ginger Snaps
Ginger Snaps 2: Unleashed
The Phantom Of The Opera (1925)-Felt sorry for The Phantom.
Peeping Tom-Felt sorry for the main character, even though he's a serial killer.

I’m very surprised nobody mentioned “Johnny Got His Gun”. Shame on you all.

The Elephant Man - Anyone who has seen this movie and still feels sorry for themselves has no soul.

Requiem for a Dream - Evokes a sadness that stays with the viewer for a very long time.

I'll join the ranks of those who say Requiem for a Dream

if they ever make the hunchback of notre dame exactly as its written then that will be a very depressing movie. the characters are all so sad and all seem to be drowning in their own mud puddle.