There are too many to decide on just one but I can name a few:
Jealous Guy - Donny Hathaway (John Lennon cover)
Superwoman - Stevie Wonder
Off You - The Breeders
I cry alone - The Black Keys
Chokechain - Lou Barlow
Every !***** song Elliot Smith has ever made
Belly Button Window - Jimi Hendrix
Emily's Dead To Me - B.C. Camplight
Side Of The Road - Beck
Enemy Of Time - Hood
Bruce Springsteen's Nebraska (The whole damn album)
Anything Morrisey has ever done
Bird Stealing Bread - Iron & Wine
Alice In Chains...well wasn't that a cry for help?
I could go on and on, though I don't find much of today's music very depressing, only because I don't think there are as many good songwriters anymore...and the "I'm grounded sitting in my room now I'm gonna trash it" music really isn't worthy.
all of Layne Stanley songs were a cry for help. Most of them were basically saying "I'm a hopeless heroin addict, I am going to die soon" or "...kill me" It wasnt until he was found dead in a PILE of syringes in his apartment in 2002 that his fans really went, "oh $hit, maybe we should have paid closer attention." His songs always make me so sad. R.I.P. Layne
joeliphious, i totally agree with you. depressing music is so much more enjoyable because you can actually feel the emotion of the person singing the song. i also might like to add that just because someone listens to sad songs doesn't make them a sad person..it just makes them human it's so good. i listen to a lot of depressing music, but my all-time favorite sad song is Konstantine by Something Corporate. give it a listen <3.
thanks, its nice to know that someone agrees with me,
my cd collection has expanded alot due to this thread, and i must say, it is quite alot better for it
thankyou! keep em coming!
boats and birds by an unsigned singer gregory and the hawk it is simply the most divine beautiful song known to man it is so bittersweet... ahh i just love it!!
god whats the name of that song..is it 'hate me today'..i dunno, its where the dude (dunno who it is either...yes i live under a rock) sings about losing his girl to drinking and hoping she moves on...i love that song.
<Added>
blue october's song...hate me today or something, yeah thats sad
searching...
R.I.P. Layne 
it's so good. i listen to a lot of depressing music, but my all-time favorite sad song is Konstantine by Something Corporate. give it a listen <3.
