[Meifa]

Sadcore is my specialty. ;P

"The One You Love," Julie Doiron
"Late Night, Maudlin Street," Morrissey
"Back to the Old House" (Hatful of Hollow version), The Smiths
"I Know It's Over," The Smiths
"Last Night I Dreamt Somebody Loved Me," The Smiths

Hell, any number of The Smiths/Morrissey songs. Heavy handed, maybe. Cliched, maybe. But I love them.

"My Hands Up," Trespassers William
"In Focus," Jim Yoshii Pile-up

Etc, etc.

 

[Dylan_Fan]

"Keep Me In Your Heart" By Warren Zevon

It is especially sad considering that he wrote and recorded it shortly before he died. It never fails to affect me whenever I listen to it.

 

[Anarchy965]

Bad Religion - Struck a Nerve. or maybe something from Pink Floyd, theres some depressing crap in Pink Floyd's The Wall

 

[Aman]

Tonight's the Night by Neil Young is an overall depressing, sad, bleak (as someone else here put it) album. It definitely is up there. In fact, I'd put Neil Young up there in general as being one of the most sad, depressing artists ever!

Mahler's 6th is particularly sad as well. Strangely enough, though, I find the number of popular artists who depict a sad tone to be very low in numbers.

 

[TommyTheCat]

"You are my sunshine"

 

[NightWoundsTime]

Black, you are my enemy
And I cannot get close to thee
Our life is ruled by enmity
And I can't weaken that
The only way that I can see
Is to hold you close to me
To love you for it's meant to be
I weaken your attack

Everything was lucked and downy
What was good was up from under
Until black, that awful tender
Came and popped my sense of wonder
All at once all eyes turned at him
Leaving me an unwatched body
And it sagged, my body's rib cage
Out from under ogler's study
Black was decomposing quickly
This was found offensive to me
His disrespect for life's proprieties
Made me scared he would destroy me

Black, you are my enemy
And I cannot get close to thee
Our life is ruled by enmity
And I can't weaken that
The only way that I can see
Is to hold you close to me
To love you for it's meant to be
I weaken your attack

So I thought I'd try to cut him
Try to force him 'neath my level
The only way to equal to him
Would be hit him with a shovel
But to really rise above him
That would be the final evil
So instead I asked the sucker
If he'd care to see my rooms
And as a friend and as a comrade
And all the things that these implied
I made him leave what it was that he had
Used to keep us unallied

Black, you are my enemy
And I cannot get close to thee
Our life is ruled by enmity
And I can't weaken that
The only way that I can see
Is to hold you close to me
To love you for it's meant to be
I weaken your attack

Now black and I we are together
Fairly just inseparable
And in the terriblest of weather
Our bonds are incorruptible

Black, you are my enemy
And I cannot get close to thee
Our life is ruled by enmity
And I can't weaken that
The only way that I can see
Is to hold you close to me
To love you for it's meant to be
I weaken your attack

Bonnie "Prince" Billy - Black

I love this song, since it's about embracing depression and making it a part of your overall personality instead of being in a constant battle and giving it the power.