Even though it has been done before, I would say Blank Page by The Smashing Pumpkins, Two Headed Boy: Part 2 by Neutral Milk Hotel, and 364 days by Murder City Devils. The last one is a good song for the upcoming holiday season.
Oh yeah, the soundtrack to Requiem for a Dream. I mean, it sounds upsetting enough, just wait until you connect the music with some other context... I'm getting disconsolate just thinking about it.
Its all in Norwegian, but its basically about a man (referred as 170, a non-voluntary soldier) who goes off to war and thinks about his family back home. And how amazed he feels like his 6 months of service have weighed on him.
Then he gets his last orders to run into danger to check to see if the enemy is cleared out. And order he says he does not want to follow and begs his officers to look after his family.
Then goes off and never reports back.
the end of the soung is still haunting... where its just
'170 er det klart, er det klart?' (is it clear? well?)
'170 me vente på et svar!' (170?! We're waiting for an answer)
Yhe ones that jump to mind are Dead Flowers, Waiting to die, and Pancho and Lefty. Apparently the chord progression from Pancho and Lefty are designed to make it more depressing.
Sieze The Day by Avenged Sevenfold
The Coldest Rain by Diecast
pretty much anything by Into Eternity ((especially the new album, The Incurable Tragedy, once you know why the 3 Incurable Tragedy songs are dated..)) [[as well as their song Into Eternity]]
Porcelain by Moby
Don't Believe A Word by Octavia Sperati
I think this song is a really depressing song. Especially if you have watched the movie (Grave of the fireflies).
I felt real depressed after watching that movie. Most of the time I am not a big fan of this kind of movies (war and/or drama), but I found this one really good.
I say for me it is Johnny Cash Hurt because he is really apologizing for all the terrible shit he did to all the people that loved him over the years. That video is so real and deep. It makes me want to cry every time I watch it.
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