I was inspired to start this thread after I watched the movie Angela’s Ashes. In fact I watched it two days ago, and I still want to slit my wrists! Great movie, but DAMN was it sad! NOTHING good happened the entire movie! I sort of like sad movies, though. I’m not quite sure why, but I do. Anyone else have any other good ones?
Most depressing Leaving Las Vegas
I was able to drink for a whole day after watching that one.
I thought the ending scene of “The Last American Virgin” was very depressing. I felt sorry for that guy.
The Deer Hunter. Oh Christ, hand ME the gun, I need to end it all now!
God yes, I have a good one.
Ever see “Sante Sangre?”
If not, I must highlight the elephant scene:
The circus boy has a pet elephant that he loves very much.
Then the elephant gets sick and dies, and the circus people have an elaborate funeral for it. The put the elephant in a huge coffin with wheels and push the cart off the cliff.
The boy watches as starving people below break open the casket and tear the elephant apart by hand, tossing out the trunk and other parts for the masses to devour.
Then there’s “I Spit on Your Grave”, but it’s not good to talk about that one in mixed company.
Taxi Driver or The Deer Hunter. Both left me unwilling to talk to other humans for at least 24 hours. (yea, I know, send a copy home so my SO can have some peace). I found both to be profoundly disturbing.
Kids.
or maybe American History X.
erm, Waterworld?
Pink Floyd’s The Wall. It was all I could do to keep from running into the street and playing in traffic after that movie. Gah.
The Killing Fields
A Clockwork Orange - I saw it the first time as a double feature with The Wall at the $1 theater in Georgetown (The old KB Cerebrus). Me and a coupla stinky homeless people taking shelter from the cold. It was a very hostile walk home from the theater.
Like Water For Chocolate – I know it’s supposed to be a happy ending, but I just found it sad.
Stalingrad – not sad, just grim; basically everybody dies and that’s about it.
Dead Poets’ Society
Leaving Las Vegas
'Night Mother
Return to Paradise, only in terms of context. Based on the setup, you really expect a nice tidy resolution, or maybe the American government to come in and fix things with guns blazing, or a tense courtroom battle. Instead, you get the inevitable brutal execution.
Fuck.
The Sweet Hereafter - Nice movie about a small town where all the kids have just died in a schoolbus accident. There’s all sorts of stuff in this movie to depress the hell out of you. Ian Holm’s character’s relationship with his daughter is what really gets me, though.
When a Man Loves a Woman is horribly depressing. Just when you think it can’t get any worse, something else bad happens. Talk about being kicked while you’re down …
The acting is good, though.
Many good nominations here. pldennison, you’re right, the ending of Return to Paradise caught me flat-footed. And kudos to mattk for Stalingrad, one of the most brutally grim movies of all time.
I’ll nominate Testament, starring Jane Alexander. It’s a post-nuclear-war drama about a small town family. They weren’t close enough to ground zero to suffer any blast damage, so over the next few weeks and months everybody gradually dies of radiation sickness. Watching it is like being slowly bled into a coma. It’s a very well-made and worthwhile movie, but Jesus, it’s a downer.
As much as I love the movie, Leaving Las Vegas always makes me really depressed. I don’t know why, exactly.
Now, if we’re talking about depressing because of how bad the movie is…okay, I won’t start making Kevin Costner/Pauley Shore jokes. How about Showgirls? 
“Seven” without a doubt. Man, I felt so much for Brad Pitt’s character. I wouldn’t have killed him so easy if it would have been my wife and child. If I had it do over again, I would not have seen “Seven” it made me feel yucky. I pay for a movie to be entertained.
“The Green Mile” although I did like the movie very much. But those poor little girls. I felt the pain that the big black dude did. I could see why he was ready to leave this place.
Schindler’s List
If that movie doesn’t make you ashamed to be a human being , you’re not.
Once Were Warriors . It ends on a positive note but it still stands as one of the most powerful movies about family violence I have ever seen .