"Tired Eyes" by Neil Young
"You're a Big Girl Now" by Bob Dylan
"Holocaust" by Big Star
"Birdland" by Patti Smith
"Hex" by Catherine Irwin
"It's Not Supposed to Be This Way" by Willie Nelson
"i'm So Lonesome I Could Cry" by Hank Williams
"I Can't Be Myself" by Merle Haggard
"He's Everywhere" by Sammi Smith
"The Door" by George Jones

Lots of Edith Frost songs are incredibly sad, but "Temporary Loan" makes me get misty every time I hear it.

American Music Club:
"What Holds The World Together"
"Can You Help Me"
"Blue & Grey Shirt"
"Gary's Song"

And about another 3/4 of their catalog.

These are some great recommendations.
I am having endless fun chasing them all up.

Thanks, keep them coming!

These homeless guys gave me their CD. There's this song called "Bird" and I swear its the saddest fucking thing I've ever heard. I'll try and post it somewhere.

Cranius wrote:(Walk Me Out in the) Morning Dew - Tim Rose

On a similar tip:

Winter's Going - Bonnie Dobson

burun wrote:Lots of Edith Frost songs are incredibly sad, but "Temporary Loan" makes me get misty every time I hear it.

American Music Club:
"What Holds The World Together"
"Can You Help Me"
"Blue & Grey Shirt"
"Gary's Song"

And about another 3/4 of their catalog.

"This year", "Nightwatchman"...

Jandek "I Passed By The Building" (which has another guy singing, not him), from the equally sad record Blue Corpse.

Sufjan Stevens "Flint (For the Unemployed and Underpaid)"

Leonard Cohen "Famous Blue Raincoat"

Tom Waits "Who Are You"

From Monuments to Masses "Sharpshooter"

Pines of Rome "Of Rose Hobart"

PJ Harvey "Legs"

Portishead "Undenied"

kerble wrote:
Guided by Voices - "Learning to Hunt" from Mag Earwhing!

Good one. Another sad GBV song is "Trap Soul Door" from Sandbox

Not slow or quiet but sad as all is Superchunk - "Without Blinking" from Foolish

Leonard Cohen - "The Stranger" from Songs of Leonard Cohen and to get specific on slowriot, "Dress Rehearsal Rag" from Songs of Love and Hate from which I dug up the inspirational passage "But you've used up all your coupons except the one that seems to be written on your wrist."

Johnny Cash (and others, he didn't write it) - "The Wall" - on one of the prison albums.

Both versions of "Lepidoptera" are pretty heart-rending.

Curses! I love many of these types of songs, but these questions always make my brain go blank.

fugazi- sweet and low
nick cave- where do we go now but nowhere
the jesus lizard- pastoral

i'll post more later. just woke up.