Lastly for now, Wooden Horse, a song by Suzanne Vega, went completely under my radar for a long time until I learned who Kaspar Hauser was…
But when I’m dead
If you could, tell them this
What was wood became alive…
These are obvious ones, but I haven’t seen them mentioned yet:
Rebekah del Rio’s Spanish cover of Roy Orbison’s “Crying” (Llorando) in Mulholland Drive;
Aimee Mann, “Wise Up”:
Flaming Lips, “Do You Realize??”
Garbage, “You Look So Fine”
Paul Simon, “Father and Daughter”, since it’s all about the father my dad wasn’t. 
And while I wholly agree with the “Anything by Leonard Cohen” statement, I find Jeff Buckley’s version of “Hallelujah” far more depressing than Cohen’s, which sounds more like some boozy revival.
And “True Love Waits”, Radiohead
Sorry, but I only posted the first verse.
:smack: Sorry, C K Dexter Haven. I somehow missed your post higher on this page.
Not the most depressing ever, but Anna Nalick’s “Breathe” has some gut-punches available when you’re in a receptive mood:
“May he turn 21 on the base at Fort Bliss
Just a day, he sat down to the flask in his fist,
Ain’t been sober, since maybe October of last year.”
She’s too young to sing a song that sad.
Listening to Warren Zevon right now, I’d have to add a lot of his songs to the list o’ most depressing songs:
“Hasten down the wind”
“Carmelita”
I am SO bummed out right now. But I’m still playing WZ.
I was burning a CD of Christmas songs today for a friend*, and broke down crying when I got to “Snoopy’s Christmas” by the Royal Guardsmen. When I was a kid, I just thought, “Oh, cool; another Snoopy song!” Now, however, I can’t hear it the same way after having seen a documentary about the WWI Christmas Truce.
*The Baron had Snoopy dead in his sights
He reached for the trigger to pull it up tight
Why he didn’t shoot, well, we’ll never know
Or was it the bells from the village below?
The Baron made Snoopy fly to the Rhine
And forced him to land behind the enemy lines
Snoopy was certain that this was the end
When the Baron cried out, “Merry Christmas, my friend!”
The Baron then offered a holiday toast
And Snoopy, our hero, saluted his host
And then with a roar they were both on their way
Each knowing they’d meet on some other day.
Christmas bells those Christmas bells
Ringing through the land
Bringing peace to all the world
And good will to man*
Another nominee: “Luka”, by Suzanne Vega.
*If you hear something late at night
Some kind of trouble, some kind of fight
Just don’t ask me what it was
Just don’t ask me what it was
Just don’t ask me what it was
They only hit until you cry
After then you don’t ask why
You just don’t argue any more
You just don’t argue any more
You just don’t argue any more*
One more from Billy Joel: “Everybody Has A Dream”.
This is my dream, my own
Just to be at home
And to be all alone
All alone with you
And I second the nomination of “Everything at all from ‘The Wind’.”
*I specifically kept to the stuff that’s not overplayed in stores and on radio. “Christmas in Hollis”, “Fairytale of New York”, “Santa Claus and his Old Lady” (okay, technically not a song), “Christmas at Ground Zero”, and so forth. I thought about adding “Christmas in Heaven” by Monty Python, but I’ve never thought it was particularly funny.
You people have got to be kidding.
Runaway Train (Soul Asylum) has to be it, hands down.
[LYRICS]*
So tired that I couldn’t even sleep
So many secrets I couldn’t keep
Promised myself I wouldn’t weep
One more promise I couldn’t keep
It seems no one can help me now
I’m in too deep
There’s no way out
This time I have really led myself astray. *
[/LYRICS]
Bathtub.
Warm water.
Razor.
Oblivion.
Björk’s song rendition of EE Cummings’ it may not always be so, called Sonnets/Unrealities XI (Track 9 of Medulla).
The poem itself is one of the most terribly depressing ones known to mankind-
What worries me is there are a couple of songs listed which sum up my life! :eek: Specifically, At Seventeen describes my life as a teenager, although I learned the truth a bit younger and Father and Son, which I’ve only heard live, performed by Moe Keale in Hawaii, sums up my relationship with my father when I was younger.
I do have one contribution: I Honestly Love You sung by Olivia Newton John. I still remember coming home from a trip to visit a college crush on which I’d learned he didn’t love me. I sat down at the piano, started leafing through sheet music at random, found that song at some point and started playing it. I was crying by the end of it.
It’s been nearly 20 years, but the memory still lingers.
CJ