Good movies that depress you

[Extra-Ordinary]

Scott Pilgrim Vs. The World
I watched it the same year I quit my band and martial arts class so when I see them making music and doing awesome kung-fu moves a piece of me says "you should have stuck with it."
*sigh* It just fills me with regret.

 

[youdontbelong]

A Scanner Darkly

Both the movie and the book

anyone who can watch that ending and read the epilogue without feeling sad has no soul

 

[Torrasque]

Oh man, there are so many...
I'm going to cop out and agree with most of the ones that people have already posted.
Schindler's List left me feeling really down, so did Hotel Rwanda and The Green Mile.

My #1 good movie that depresses me is Jin-Roh: The Wolf Brigade.
That movie makes Schindler's List look like a comedy =|