[irishsammy]

I've always been touched by R.E.M.'s "Let Me In" from the Monster album:

Yeah, all the stars drip down like butter,
Promises are sweet,
We hold out our pans, lift our hands to catch them.
We eat them up, drink them up, up, up, up

Hey, let me in.
Hey, let me in.

I only wish that I could hear you whisper down,
Mister Fisher moved to a less peculiar ground.
He gathered up his loved ones and he brought them all around
To say goodbye, nice try.

Hey, let me in. yeah yeah yeah
Hey, let me in. Let me in.

I had a mind to try to stop you. Let me in. Let me in.
But I've got tar on my feet and I can't see
All the birds look down and laugh at me.
Clumsy, crawling out of my skin.

Hey, let me in. yeah yeah yeah
Hey, let me in.
Hey, let me in. yeah yeah yeah
Hey, let me in.

It's supposed to be dedicated to Kurt Cobain which is sort of touching in itself but I also discovered it around the time a close friend/second father passed early and the lyrics really got to me.  I have never been able to make it all the way through the song without losing it.   

And at the very least, it's one of the coolest uses of guitar distortion I've ever heard.

[clarkjohnsen]

There's an, ah, amusing movie called The Saddest Music in the World, directed by Guy Maddin -- representative of Canadian avant-garde cinema, so watch out!

"A double-amputee beer baroness invites musicians of all nations to compete in a grand competition to find the world's saddest tune... in Winnipeg. The only thing zanier than the plot is Maddin's style, which makes the film look like a lost artifact from the Cabinet of Dr. Caligari era, a jumble of Expressionist compositions and gauzy focus. It helps if you're already a fan of the director of Careful and Dracula: Pages from a Virgin's Diary, for this is not Maddin's most cohesive picture. Kids in the Hall stalwart Mark McKinney is a little too arch as a sharpie returning to Manitoba, but Isabella Rossellini is delicious as the "Beer Queen of the Prairie." By the time she straps on a pair of hollow glass legs filled with bubbly lager, you're either delighted by this movie or you've given up."

http://www.amazon.com/Saddest-Music-World-Isabella-Rossellini/dp/B00062IXJW/ref=sr_1_1?ie=UTF8&s=dvd&qid=1278016472&sr=1-1

[1ZIP]

Brook Benton - "Rainy Night in Georgia"

http://www.youtube.com/watch?v=yRKqfrct070&feature=related

[KnowTalent]

most anything from the Nick Drake library...very dreary stuff.
REM's "Everbody Hurts" is another

although more bittersweet than sad, Dave Grohl's (Foo Fighters) acoustic version of "Everlong" where he laments over relations with his ex-wfie is soft yet still soul crushing imo

Hello
I've waited here for you
...Everlong

Tonight
I throw myself into you
And out of the red, out of her head, she sang

do, do, do do, do, do, ........

Come down
And waste away with me
Down with me

Slow how
You wanted it to be
I'm over my head, out of her head she sang

do, do, do do, do, do, ........

And I wonder...
When I sing along with you
If anthing could ever feel this real forever?
If anything could ever be this good again?
The only thing I'll ever ask of you
You've got to promise not to stop when I say when
....She sang

do, do, do do, do, do, ........

Breathe out
So I can breathe you in
Hold you in

And now
I know you've always been
Out of your head, out of my head I sang

do, do, do do, do, do, ........

And I wonder
When I sing along with you
If anything could ever feel this real forever?
If anything could ever be this good again?
The only thing I'll ever ask of you
You've got to promise not to stop when I say when
She sang

do, do, do do, do, do, ........

[lcrim]

I realize this thread has been around for a while and its been instructive to me to learn more about some people.
There is a classical piece by Samuel Barber written back in the 1930's, now usually referred to as Adagio for Strings, that I've heard played at many funerals and it always gets to me.  It's been used in many soundtracks including Oliver Stone's Platoon and David Lean's Elephant Man.  It's been sampled in countless trance pieces and even been used on the Simpsons.

[CSI]

A Cottage For Sale - Frank Sinatra

Written for an earlier generation, it is still poignant in our age of divorce and broken households.

The lawn we were proud of
Is waving in hay
A beautiful garden
Has withered away
Where you planted roses
The weeds seem to say
A cottage for sale

[jimdgoulding]

CSI, nice one.

[1ZIP]

David Grey - "Shine"


I can see it in your eyes
What I know in my heart is true
That our love it has faded
Like the summer run through
So we'll walk down the shoreline
One last time together
Feel the wind blow our wanderin' hearts
Like a feather
But who knows what's waiting
In the wings of time
Dry your eyes
We gotta go where we can shine

Don't be hiding in sorrow
Or clinging to the past
With your beauty so precious
And the season so fast
No matter how cold the horizon appear
Or how far the first night
When I held you near
You gotta rise from these ashes
Like a bird of flame
Step out of the shadow
We've gotta go where we can shine

For all that we struggle
For all we pretend
It don't come down to nothing
Except love in the end
And ours is a road
That is strewn with goodbyes
But as it unfolds
As it all unwinds
Remember your soul is the one thing
You can't compromise
Take my hand
We're gonna go where we can shine
We're gonna go where we can shine
We're gonna go where we can shine

(and look, and look)
Through the windows of midnight
Moonfoam and silver

[charmerci]

I'm going to throw a wrench to the monkey in here.  ( - or something like that....)

The saddest jazz instrumental is -

Time After Time - Ben Webster and Associates


Even though this song isn't sad per se and I don't understand Portuguese, her voice can move me to tears sometimes.

O Bebado E O Equilibrista - Elis Regina

http://www.youtube.com/watch?v=6kVBqefGcf4

I can't find a recording of this version but this one is almost as good - and higher quality of course.

http://www.amazon.com/Minha-Historia-Elis-Regina/dp/B000008C32/ref=sr_1_1?ie=UTF8&s=music&qid=1282302067&sr=8-1

[roymail]

Another vote for...
Sarah McLachlan, Arms Of An Angel
http://www.youtube.com/watch?v=jVbkz_3lO3c

I can't listen to that song without being moved.