"Sometimes" by Candlebox...I don't know if this song was meant to be sad...but I've always felt a little twinge in my heart when I listen to it, especially these lyrics:

We change directions, we watch the tides
And we borrow too much
We form restrictions and we form lines
And we separate you from me
Sometimes, sometimes we carry more weight than we own
Oh but sometimes sometimes goes on


Candlebox – Sometimes – Listen free and discover music at Last.fm

Alice in Chains - Nutshell, Rotten Apple, Down in a Hole are all beautifully depressing.
Pearl Jam - Black, Last Kiss
Ben Folds - Brick, Mr. Jones part 2
Johnny Cash - Hurt
Collective Soul - The World I Know
Neil Young - My My, Hey Hey (Out of the Blue), Cortez the Killer, The Needle and the Damage Done
Bruce Springsteen - The River
Phil Collins - Another Day in Paradise
The Who - Behind Blue Eyes
Bill Withers - Aint No Sunshine
Fleetwood Mac - I'm So Afraid
Lynyrd Skynyrd - Simple Man, All I Can Do is Write About It
Counting Crows - Perfect Blue Buildings, Anna Begins, Round Here all their music makes me kind of sad
Pink Floyd - Wish You Were Here
Dave Matthews - American Baby

Not sure if all of these songs are supposed to be sad but they sure bum me out. Great for rainy days.

About half of Ben Folds discography, especially Fred Jones Pt. 2 and Prison Food

Fred Jones Pt. 2 is the pinnacle of his work :thumb:

Carrying Cathy is a sad one by him too.

World's End Girlfriend, all of their songs

I don't really know his music much beyond the singles but "Brick" is certainly a hell of a depressing song. I didn't even realize how depressing until someone explained what it was about to me.

It's always fun explaining what that song is about to high school girls who think it's about a breakup or something like that.

i'm not sure about "saddest of all time" but this song in particular can be hard to listen to at times, but it has a great meaning behind it.

A few Cohen tunes:
Seems So Long Ago, Nancy
Avalanche
Dress Rehearsal Rag
The Letters
Hallelujah (A different kind of sad)
Death Of A Ladies Man (Another strangely sad one)-
Ah the man she wanted all her life was hanging by a thread
"I never even knew how much I wanted you," she said.
His muscles they were numbered and his style was obsolete.
"O baby, I have come too late." She knelt beside his feet.
"I'll never see a face like yours in years of men to come
I'll never see such arms again in wrestling or in love."
And all his virtues burning in the smoky Holocaust
She took unto herself most everything her lover lost
Now the master of this landscape he was standing at the view
with a sparrow of St. Francis that he was preaching to
She beckoned to the sentry of his high religious mood
She said, "I'll make a place between my legs,
I'll show you solitude."

He offered her an orgy in a many mirrored room
He promised her protection for the issue of her womb
She moved her body hard against a sharpened metal spoon
She stopped the bloody rituals of passage to the moon

She took his much admired oriental frame of mind
and the heart-of-darkness alibi his money hides behind
She took his blonde madonna and his monastery wine --
"This mental space is occupied and everything is mine."

He tried to make a final stand beside the railway track
She said, "The art of longing's over and it's never coming back."
She took his tavern parliament, his cap, his ****y dance,
she mocked his female fashions and his working-class moustache.

The last time that I saw him he was trying hard to get
a woman's education but he's not a woman yet
And the last time that I saw her she was living with some boy
who gives her soul an empty room and gives her body joy.

So the great affair is over but whoever would have guessed
it would leave us all so vacant and so deeply unimpressed
It's like our visit to the moon or to that other star
I guess you go for nothing if you really want to go that far.

It's like our visit to the moon or to that other star
I guess you go for nothing if you really want to go that far.

It's like our visit to the moon or to that other star
I guess you go for nothing if you really want to go that far.

River-joni Mitchell
where did you sleep last night-Nirvana
Ashes of American flags-wilco
I actually find the song disco 2000 by pulp to be pretty sad for such an upbeat song its quite devastating
Please dont anyone say imagine by Lennon that song is just ****ing terrible