Soul crushing songs

OHHHHH I almost posted 'The Silent Boatman', good call.

Three favorites I forgot -
Kate Bush - This Woman's Work (Sadly or not, will always associate this with its "She's Having a Baby" use)
Paul Kelly - How to Make Gravy
The Weakerthans - Plea from a Cat Named Virtute ("I know you're strong.")

I like "wibbly" as a description. If iPod listening to these at work, have to make sure it's not pre-meeting, to avoid watery eyes.

80% of all Hank Williams songs, even some of the happy ones

Rickie Lee Jones - On Saturday Afternoons in 1963. (The part that gets me is when the orchestra comes in - "Years go by...years go by...")
Melanie - Some Say (I Got Devil)
Marianne Faithfull - Who Will Take My Dreams Away
Thinking Plague - Fountain Of All Tears
Tindersticks - Walking

Take it to the limit

Lee Hazlewood - My Autumn's Done Come

https://www.youtube.com/watch?v=dW6YQYlftCE

i know people here don't like the guy who sings this but:

i know i'm not supposed to say i'm sorry
i know you've had more loves than mata hari
but you're the star of my life story
and i'm so sorry

https://www.youtube.com/watch?v=vjZ7x4mkaxE

That's the way things go
All people's changes they grow
I hide in this room
Let's hope it's not wasted
Oh, it's such a shame

this one though

https://www.youtube.com/watch?v=jzWYUomBpwg

Surely don't stay long I'm missing you now.
It's like I told you I'm over you somehow
Before I close the door
I need to hear you say goodbye
Baby won't you change your mind?

this one isn't fair because it's one of the best songs ever

Terry Callier - Dancing Girl
For Against - Daylight
Joy Division - Twenty Four Hours
Christian Death - The Drowning
Ceremony - I Heard You Call My Name
Comsat Angels - On the Beach

If I'm reaching for the crushing Mazzy Star, I'm reaching for "Into Dust".

That reminds me ...

Jackson C. Frank - Milk and Honey

I messed up someone's day after recommending that one.

Started a playlist of this thread last night. Looked at it this morning and thought "Oh god, what have I done," as putting all these depressing songs together in one place is possibly not the best idea anyone has ever had. But still.

http://www.youtube.com/playlist?list=PLUh3oHWXrJrRKOH5MrGVHmbNqiU5gyJdT

yes, Pheel! i need this right now, these can be soothing when you're in distress...

Nillson / Don't Forget Me (or Marianne Faithful's version)

"Alien Observer" - Grouper

Look into the night sky
Looking towards the big lights
Looking towards the freeway
Morning subway passes by my window

I feel it in the darkness
I need to feel it sometimes
I need to fall asleep
Morning never is too far behind

Gonna take a spaceship
Fly back to the stars
Alien observer
In a world that isn't mine

The Associates - Party Fears Two

Kate Wolf singing Sandy Denny's 'Who Knows Where the Time Goes?':

https://www.youtube.com/watch?v=DgauX0bnN-0

my soul:

https://i.imgur.com/jb9Hmh9.gif

reminded me of
https://www.youtube.com/watch?v=mD1UY6KK-bc

But that cover does nothing to my soul compared to the original. Sandy Denny's voice is the ultimate soul crusher:

https://www.youtube.com/watch?v=5oBMDcLf6WA