i’m gonna have to go with “last night i dreamt that somebody loved me” by the smiths. i don’t even have to type out the lyrics. the title says it all…
most. depressing. song. ever.
(but also really beautiful)
How about “Sylvias Mother” Dr. Hook. IIRC written by Shel Silverstien
"And the operator says40 cents more
for the next
three
minutes
Pleeeease Mrs. Avery
I just got to talk to her
I’ll only keep her a while
Please Mrs. avery
I just want to tell her
good bye…tell her good bye…"
Did I miss it or did you guys leave out Meatloafs “Two out of Three Aint Bad” ?
Actually, now that I think about it, Dr Hook did a song called “Carrie” that is even sadder.
"Second street and Broadway
sittin in door way
head held in his hands
looked upon the world
like he was praying
Foot wrapped in an old rag
bottle in a brown bag
then I heard the words
that he was sayin
and he said…
come on Carrie
carry me a little farther
come on Carrie
carry me one more mile
I don’t know where it’s leading to
but I know I can make it if I lean on you
soo…"
I can’t go on. My God that is a sad song.
I’m fairly new to rock, only having started listening to it over the past two years so I haven’t hit the point where I want to bash my head into the wall every time I hear it yet. 
Another Don Henley song - The Last Worthless Evening
For me the most depressing song would be
Thank You by Dido
It was the song for me and my ex, I cant listen to it without crying
Close second would be
Tracks of my tears by smokey robinson
I have to suggest… well, any song by the Tear Garden, but two in particular:Judgement Hour is about a bitter, elderly divorced couple:
… and You and Me and Rainbows is about… well, I’m not entirely sure what it’s about, but it involves drug use somehow. And regret. And false hope. In spades.
The lyrics to these songs themselves are downer enough, but the real kicker is Ka-Spel’s incredibly dry, hopeless, resigned vocal delivery.
Another Sattellite
by XTC
My heart is taken it’s not lost in space
And I don’t want to see your mooney mooney face
I say why on earth do you revolve around me
Aren’t you aware of the gravity
Don’t need another satellite
I’m happy standing on my feet of clay
I have no wish to swim your milky milky way
I say why on earth do you send your letters 'round here
Only to gum up the atmosphere
Don’t need another satellite
So circling we’ll orbit another year
Two worlds that won’t collide
So circling we’ll orbit another year
Moon still tries to steal the tide away
Don’t need another satellite
Don’t need another satellite
Abort your mission let’s just say you tried
Before you glimpse I have a darker darker side
I say why in Heaven’s name do you come on these trips
Only to freeze in a total eclipse
Don’t need another satellite
So circling we’ll orbit another year
Two worlds that won’t collide
So circling we’ll orbit another year
Moon still tries to steal the tide away
Don’t need another satellite
Don’t need another satellite
Definatly. One of the few songs that make me cry every time I hear it .
I have to second Love Will Tear Us Apart Again. Dang. Poor Ian. I still get choked up at the pure, desperate agony of that song.
There’s a famous korean song by one Jo Sungmo, and its called For Your Soul. Its about a couple that are about to be married, and on their wedding day or when he is going to ask her to marry him, the girl is murdered in his arms, and right before she dies, he places a wedding ring in her hand.
The lyrics to the song, translated by my insufficient korean, go something like this:
The people to bless our wedding were going to come
Don’t think that there was no one else besides us
At this time, you have to make your wedding vow to love me for the rest of your life
But if you don’t answer, its ok, I can say it for both of us.
And as I weep, I clutch your picture to my heart, wet with tears,
Why on this wonderful day, even you…it was your last heartfelt wish
I send you on your way,
take this ring
dont lose it, grasp it tight
and when the day comes that our paths meet again,
I’ll take the ring and put it on your finger
Go, don’t be afraid.
And now you’re gone;
The sound of desolate wind suddenly rushes in
Will you be able to take this long road without me?
Why can’t I take you?!
When the first snow comes, or when it rains,
come and visit me
always on this day, you must come to me
In my song, in my dreams,
I send you on your way,
take this ring
dont lose it, grasp it tight
and when the day comes that our paths meet,
I’ll take the ring and put it on your finger
And even if I’m late, please wait for me.
I was in korea, and I had heard the song once in a music shop, so I knew what the tune was like. I was intrigued, so I bought the lyrics/music. I set to work to translating them, and when I was done, I could hardly read them without my eyes welling up with tears. I just imagined this poor beautiful girl, separated from her love taking this long, lonely, desolate path by herself, perhaps looking back from time to time. I don’t know. Just puts a knot in my throat. Its such a beautiful, mournful song.
D’oh yes your right, Ian Dury is the bloke from the Blockheads? Yes the rest of Joy division wrote the instrumental parts to the song as well.
A slightly obscure and sad little Dan Fogelberg song, Why Is Love Always The Last To Know:
Living in a house of cards
praying the wind doesn’t blow too hard
Living in two differences
Straining to keep up appearances
Freedom is near but seems to elude you
Trying to change your dreams into what your needs allow
It should be easy by now.
Why is love always the last to know?
Also, I second Meatloaf’s Two Out Of Three Ain’t Bad.
Sandy Denny - I’m a dreamer.
Haunting song about someone who is in the act of deciding wether or not, to quit a relationship of which they had great hopes.
http://www.concentric.net/~jpdaspit/fotheringay/lyrics.htm
The last line of the song is misleading at first, she says she thinks she will probably stay, but the way it is sung its clear that she will leave, and betrays just how torn bween the two options she is.
Back for more…
Missing You – John Waite
- ain’t missing you at all
Since you’ve been gone
Away
I ain’t missing you
No matter
What I might say *
How Would I Know – Melissa Etheridge
You might believe there’s a paradise
In the next hello
How would I know
If you don’t tell me so
Love Has No Pride - Bonnie Raitt. Just kill me now. This is one of my “Cryin’ and Vaccuumin’” songs.
Oh… You mean “depressing good”??? I thought you meant depressing like it stunk to high heaven. The first song that came to mind when I read the thread title was this song I remember from when I was a kid listening to the radio in the back seat of my parents car…
RUN, JOEY, RUN by DAVID GEDDES
[ANGELIC CHOIR AHH-ING]
[Voice of Julie, who sounds approximately 12 years old]
Daddy, please don’t - it wasn’t his fault
He means so much to me
Daddy, please don’t, we’re gonna get married
Just you wait and see
[Joey (David Geddes):]
Every night, the same old dream
I hate to close my eyes
I can’t erase the memories
The sound of Julie’s cries…
She called me up, late that night
And she said, “Joe, don’t come over
My dad and I just had a fight
And he stormed out the door
I’ve never seen him act this way
My God, he’s goin’ crazy
He say’s he’s gonna make you pay
For what we’ve done
He’s got a gun so
RUN, JOEY, RUN, JOEY, RUN!”
Even when I was 8 years old and had not developed any kind of taste, this song turned my stomach.
Man, I found this thread late, but there are some really good songs mentioned here. My top choices have all been mentioned already. Cormac36 introduced “If You Could Read My Mind” by Gordon Lightfoot, but left out my favorite lyric in that song:
When you reach the part
Where the heartache starts
The hero would be me
I also second Operator by Jim Croce:
Operator, will you help me place this call?
I can’t read the number that you just gave me.
There’s something in my eye
You know it happens every time
I think about the love that I thought would save me
Gyan9 said “I don’t know if you can call U2’s One depressing.”
Well, I do:
Did I disappoint you?
Or leave a bad taste in your mouth?
You act like you’ve never had love –
And you’d like me to go without.
Well, sad in a bitter sort of way.
One I haven’t seen brought up yet is Harry Chapin. (Most of his songs are depressing.) W.O.L.D. is depressing and bitter, but a more forlorn love story that’s depressing is Taxi:
*There was not much more for us to talk about,
Whatever we had once was gone.
So I turned my cab into the driveway,
Past the gate and the fine trimmed lawns.
And she said we must get together,
But I knew it’d never be arranged.
She handed me twenty dollars for a two fifty fare,
and said “Harry, keep the change.”
*
I can’t decide whether I want to wallow in the melancholy this thread brings, or go find a saccharine happy thread as an antidote.
Oh Gods, Harry Chapin deserves a "depressing song thread of his own. WIth only a couple of exceptions (Circle, and 30,000 Pounds Of Bannas -which itself is funny/depressing) all of his songs are so depressing they practically put the instrument of suicide in your hand.
That’s true. But the only person who could write a suitable tribute to Harry Chapin would be… Harry Chapin. (Or perhaps Jim Croce, but he’s not around to do so either.) Then again, his songs seem pretty self-referential, in hindsight.