Democratic Underground - "The Chalet Lines" by Belle & Sebastian

Possibly the most depressing song ever written. Features only vocals, a soft piano, and a nearly nonexistent cello part.

He raped me in the chalet lines
The girl I shared with was away for the night
I couldn't get up for my shift today
I'll have to leave the camp now anyway
I'll go to London there's a mate of mine I know
she'll give me a place
Full of woe and further to go
She caught the bus
"Oh I'll go anywhere"
She caught the bus
Her face was just a smear on the pane

He raped me in the chalet lines
I had just said no for the final time
Although it's last month it's like yesterday
I missed my time, I don't think I could stand
To take the test, I'm feeling sick
Fuck this, I've felt like this for a week
I'd put a knife right into his eyes
My friend can't see
She asks me why I don't
Tell the law
Oh what's the fucking point at all

He raped me in the chalet lines
It was a party, it was going fine
With the boys from the amusement park
A few were idiots, they were a really good laugh
They had the shows on till way after dark
I hope she'll give me a place
Full of woe and further to go
She caught the bus
"Oh I'll go anywhere"
She caught the bus
Her face was just a smear on the pane

Runner up: "Asleep" by the Smiths

Okay, this is the second saddest song ever written. Here's a hint: he's not singing about sleeping. This is another vox/piano song, only this one features howling winds and a music box in the background.

Sing me to sleep
Sing me to sleep
I'm tired and I
I want to go to bed

Sing me to sleep
Sing me to sleep
And then leave me alone
Don't try to wake me in the morning
'Cause I will be gone
Don't feel bad for me
I want you to know
Deep in the cell of my heart
I will feel so glad to go

Sing me to sleep
Sing me to sleep
I don't want to wake up
On my own anymore

Sing to me
Sing to me
I don't want to wake up
On my own anymore

Don't feel bad for me
I want you to know
Deep in the cell of my heart
I really want to go

There is another world
There is a better world
Well, there must be
Well, there must be
Well, there must be
Well, there must be
Well ...

Bye bye
Bye bye
Bye ...

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