Pretty much anything by Gary Numan:
I Die: You Die
Me, I Disconnect From You
Complex
Are Friends Electric?
Please Push No More (!!)
*
Also, Always the Sun by The Stranglers.
Godspeed You Black Emperor! - Dead Flag Blues
Black Heart Procession - Waterfront (The Sinking Road)
Tom Waits - Georgia Lee
Weezer - Butterfly
Archers of Loaf - White Trash Heroes
Interpol - Untitled
Pixies - Caribou
fun!
Fancy -Reba McEntyre
not my favorite song, but frickin depressing!
Hello (Turn Your Radio On) - Shakespear’s Sister
“Life is a strange thing
Just when you think you’ve learnt how to use it, it’s gone”
Sponge has two depressing songs back to back on their Wax Extatic cd " I Am Anastasia" (abused girl or woman) and “Silence is Their Drug” (ok, so the latter is enough cynicism to drive one to the point of suicide rather than “sad” but that’s still depressing, right?)
Then there’s " Hold her Down" by Toad The Wet Sprocket and " Me and my gun" by Tori Amos (both about rape)
" Now What?" by Possum Dixon (a friends bad relationship distroying their friendship)
" Gone Away" by The Offspring (a loved one’s death)
“Santa, I’m Right Here” by Toby Keith (homeless child writing to santa)