I agree, but the Johnny Cash cover still chokes me up at times. He seems to be referring to a more human love, while I always took Reznor to me loathing a heroin addiction. Might be wrong though, of course.
Yes, I agree. Iron and Wine is fantastic for a brooding, mellow mood. Great stuff.
[b]Hey everybody i think by far the saddest song ever made is R.E.M-shining happy people.The topic is just sooo morbid!
but on a more serious note i think theses are pretty sad,however they are also very good:
2pac-my block
dmx-dear grandma
2 pac-dear mamma
aalyiah-i miss you
lighthouse family-run
bruce springstein-streets of philadelphia
if you have any comments on this let me know then i can either sing your praises or annilate you in to a jibbering wreck with my mind shattering banter 
[/b]
all worthy songs are sad!
at the moment for me the saddest is by A-Ha - Forever not yours
ATM mine would be Mandible chatter - Tangle in delirium
No-one sings, its just the guitars and the technical sounds are mystifying as if your been teleported through different lands and feelings. Then a women in the background just hums, all eerie but simple simple.
Before that i would say Korn - Daddy.
Its basically about him been raped as a child by his uncle, but in the song its his dad. Again, a women in the background near the end sings mamma boy nice and quietly with johnathan davis crying, and the guitars making it all sound evil and sad.
C’mon, guys you can do better (worse?). These are all sad, check them out when you’re in a dark mood:
Mercy Street - Peter Gabriel
Let’s Go Out Tonight - The Blue Nile
A Face In The Crowd - Tom Petty
Desperados Under The Eaves - Warren Zevon
Take it With Me When I’m Gone - Tom Waits
Waiting For A Miracle - Leonard Cohen
Stay - U2
Brothers In Arms - Dire Straits
Nobody Home - Pink Floyd
Sugar Mice - Marillion
Just a few to start with, off the top of my head…
there is a whole genre of sad music called post-rock… the sadest of the sad is probly “A Silver Mount Zion”…
“Fatherless at 14” By Kendall PAyne
“Oh Brenda Jean, My Peanut butter queen, Innocent and Bright dont think of me as mean. Sweet Brenda Jean for all you have not seen, You know i hate to leave you fatherless…at 14.” Its about a little girls dad dying.
“Missing” By Evanescence
“Even though I’m the sacrifice, you wont try for me not now, Though I’d die to know you love me, I’m all alone…Isnt something missing, isnt someone missing me.”
I’m not sure the story of this one but it makes me cry.
“She” and “Forever 17” By Zoegirl
“She’s alone, caucht up in the undertoe, where it takes her no one knows, cos thats how it goes, thats how it goes when we throw stones.”
(SHE) this ones about a girl who gets into big trouble with her life and no one will help he just condemn her.
“Ill never have a bed to make, a test to take a summer day, I’ll always be forever seventeen” THis one is about a girl who was killed by a drunk driver.
“Elle. G” By the News Boys
“…Next Life could you kindly refrain - from throwing yourself at the mercy of a train…”
or godspeed you! black emperor
http://www.southern.net/southern/band/GDSPD/sounds/moya.ra.ram
^if you’re wanting sad that should work for you…
One of my turns Pink Floyd The Wall album.
try
DONT take the girl
or
Live like you were dying
sad songs
It’s So Hard to Say Goodbye (to yesterday) by Boyz II Men
Dear Mama by Tupac
Grandma by DMX
Jack Johnson’s On and On album is somewhat simultaneously both mellow and depressing.
Iris by Goo-Goo Dolls
Mmm. I never though I would say this put I actully quite like…
Britney Spears - Everytime
There I’ve said… No one will ever take me seriouslly again!
The main theme song from the movie Donnie Dark…The name of it is “it’s a cold world” but I cant remember who it’s by.
do you mean ‘mad world’ by gary jules?
radiohead- most of them, how to disappear completely, or fake plastic trees.
bush- chemicals between us, glycerine, Inflatable.
cold play- a few, rush of blood to the head, we never change.
Staind- Epiphany, outside
pink floyd- several like, comfortably numb
Ben Harper- give a man a home, alone.
limp bizkit- behind blue eyes
u2- one
Suicide is Painless
REM- everybody hurts
A few of audioslave
Soul Asylum- runaway train
Depression, such a feeling, such a high.
Cavatina by Stanley Myers (Theme from the Deer Hunter).
I know that to start on orchestrated music would make the list very big.
But violin sonates by Alfred Schnittke and the second/third (can’t remember exactly) movement of the first symphony by William Walton, I think very subtly conveys the notion of going from sadness to grief to absolutely being destroyed by grief. Where it kinda comes at a suprise that it can go deeper…
If you want to experience some sadness, classical is surely an option worthy of exploration although it takes a bit more patience to tune into stuff.
In another context Britney Spears is ofcourse very sad as well 
Somebody has to post this kind of snobbery (I’m not sure I’m sorry)
it’s originally by nine inch nails…
but the saddest song/best song has to be
fade into you by mazzy star
I think the saddest song ever is “wild horses”. The version that was in the movie “fear”. Heard it today for the first time in awhile, very sad and beutiful. some more:
george micheals-teacher: (my friend use to sing it before he moved to florida) every time i hear it, i think of him and miss him, he was a true friend.
enya-any slow song, I think she has the best female vocals ever.
laura McKennit-it’s that voice
Clannad- voice again
I’m such a weeny.