I've never made it through 'Midnight Cowboy' from start to finish. I've seen the whole thing, but only in parts; every time I try to watch the whole thing I just want to jump out a window about halfway through. Tried it again just now (it's on the Retro channel.) GAH, it's SO FUCKING DEPRESSING.
Original Post
Without a doubt, it's What Ever Happened to Baby Jane? It's so horrific and depressing that I felt physically ill by the end of it.

Jules et Jim was no picnic either.

Woke up this morning MY house was cold

Star Wars Episode 1. I had the same feeling Doaksie had.

"I had nothing to offer anybody except my own confusion."

What was that one with Sean Penn as the son of ex-con Christopher Walkin. Some cute young thing falls for sean penn, but you know the whole thing is going to end in the shitter.

Madonna sang one of her better ones for the soundtrack.

And In the Bedroom. Though that was made more depressing after the film ended and my (then) husband said he totally empathized with the killer. That's partly why he's my (then) husband, I suppose....

Never separate the life you live from the words you speak. - Paul Wellstone

I dont think this qualifies as depressing, but it sure made me sad: "Terms of Endearment." Really, really sad. That ending scene, of the kids at the hosptial bed, saying goodbye to their mom. Damn tough scene.
"What is she, the governor of Guam?"
'Requiem for a Dream'
Just when they think they have all the answers, I come and change all the questions.
Badlands, with Martin Sheen and Sissy Spacek, is another great little film that's very depressing.

And Sheen also puts me in mind of Apocalypse Now.

Woke up this morning MY house was cold

It's a toss up between Looking For Mr. Goodbar and All That Jazz, which wasn't about fucking jazz at all.
Stipped of my rand.
I'd put Boys don't cry on that list.
I've seen some others that qualify as well.

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The taste of your voice reveals what before was unknown.
Do you ever dream of the world like I do?

I almost forgot Gegen die Wand (Head on aka Against the Wall) - very good but very depressing movie.

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The taste of your voice reveals what before was unknown.
Do you ever dream of the world like I do?

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