What are some good depressing movies? I’m in the mood for one tonight, but I have no ideas.
Dancer in the Dark starring Bjork. I practically never cry at movies but the end of that one just takes a lot out of you. Wow.
The Pledge.
Watership Down.
Osama
Rabbit Fence
Terms of Endearment (An oldie but goodie)
Go medieval – A Walk With Love and Death (John Huston) or The Navigator. Can’t get much bleaker than those two.
Once Were Warriors
but very well done -Aussie
Boys Don’t Cry (the one with Hillary Swank)
Schindler’s List
Might I recommend my double feature from last weekend:
Mystic River
21 Grams
Guaranteed to lift your spirits!
The World According to Garp. Especially if you’ve read the book and you know what’s coming.
Last Exit to Brooklyn
If you’d like an oldie, try WOMAN IN THE WINDOW, directed by Fritz Lang, with Edward G. Robinson…
CK, I love that movie! TMC runs it occasionally. Good choice.
The House of Sand and Fog is the poster movie for depressing.
“Grave of the Firelies” will make you weep bitterly for days.
and then you’ll be ready for the soul-crushing grief of “Gummo.” 
Leaving Las Vegas
Yep.
Requiem for a Dream is a laugh riot too.
Testament
I’d say Johnny Got His Gun beats that one out.
See also: Butterfly Kiss.
It was NZ, wasn’t it?
Shadowlands, The Hours