I mean, EVER.

I think some nice depressing songs are:
Ashes to Ashes (David Bowie)
Rosie Won't You Please Come Home (the Kinks)
Time For Heroes (the Libertines)
Tangled Up In Blue (Bob Dylan)
Rock N Roll Suicide (David Bowie)
Radio America (Libertines)
The Winner Takes It All (ABBA- yeah I'm lame, what of it!)

but I don't think I know the most depressing song ever...

Artist: Jewel
Song: Adrian
Album: Pieces Of You

Adrian came home again last summer
Things just haven't been the same around here
People talk
People stare
Oh, Adrian, come out and play

An unfortunate accident in a canoe
Dr. said, 'I'm sorry, not much I can do'
The air was so still
His eyes did not blink
Oh, Adrian, come out and play

Little Mary Epperson liked him
She vowed always to watch after him
Still he did not move
Dr. said it's no use
Oh, Adrian, come out and play

She sat by his side, watched the years fly by
He looked so fragile, he looked so small
She wondered why he was still alive at all

Everyone in town had that 'I'm so sorry look'
They talked in a whispered hush, said
'I'd turn the machines off'
But still she sat by his side
Said, 'life he won't be denied'
Oh Adrian, come out and play

Yellow flowers decorate his bedroom
Sign above his door says Welcome Home
But he just sits and stares
He's awake but still not there
Oh, Adrian, come out and play

She sat by his side, watched the years fly by
He looked so fragile, he looked so small
She wondered why he was still alive at all

And little Mary Apperson grew up lovely
She still comes to visit him on Sundays
He's like an unused toy
He's got big hands but the mind of a little boy
Oh, Adrian, come out and play

Adrian came home again last summer
Things just haven't been the same around here

Only Gary Jule's version of Mad World. That's depressing.
The Tears for Fears original is more poppy, but somehow much more complex because of it...
-both version are great. :)

Wonderful world by Louis Armstrong is indeed depressing.

Pretty much anything by Tom Waits: Music to kill yourself to. And lots of stuff by Leonard Cohen... I can't be specific because I don't like either and find most of their stuff almost drives me to the brink :)
I could also say anything by Mariah Carey, Salene Dion, Britney Spears, N'sync (and all boy bands) and about a thousand others but Tom and Leonard are real musicians and depress through the tone and subject matter while those other morons depress through their vapidity.

Sky Pilot -by the Animals. That's very sad.

Puff The Magic Dragon -by Peter Paul and Mary?

Knock'n on heavens door -Bod Dylan.

Walk on the Wild side - Lou Reed.

i was going to say Wonderful world by Louis Armstrong is depressiing ozoneocean and but Walk on the Wild side Lou Reed is not sad.and i geuss Adrian is just sad when i was a kid i was really depreing but i colud play it paying banjo kazooi and played maro smash to that violinn guy.

Tom Waits terrifies me... yuughh...
good call on puff the magic dragon, too! that one... is embarrassingly sad.
(also "I'm through with love" by sarah vaughn... she sounds like she's ready to kill herself when she sings it)

"Tears", by X-Japan. =P Also, "Everybody Hurts" by R.E.M. and "Wish You Were Here" by Pink Floyd.

If you take a look at the lyrics for "Gotta Knock a Little Harder" by Yoko Kanno, you'd notice that the song is very depressing. "Lighting Crashes" by Live is another sad song about life and death. Both "I Lied" and "At The Edge of the World" by electronica band Telefon Tel Aviv are great samples of fantastic harmonic sad songs. (...honorable mentions go out to the wordless "Sound in A Dark Room" and "Map of What is Effortless")

Stereophonics also has a great sad song about breaking up called "Since I Told You It's Over" Primitive Radio Gods has a dreamy sad-ish song called "Standing Outside a Broken Payphone With Money in My Hand" of course no such is a mention with out Pink Floyd's "Marooned" and "Comfortably Numb". Others? Electric Light Orchestra's "Strange Magic", The Eagles' "I Can't Tell You Why" and "New York Minute" Last? Gerry Rafferty's classic "Baker Street" the story of a man that drinks too much.

Now the last two are just great samples of powerful sad songs, Pearl Jam's "Black" where Eddie's lyrics about love and losing it really bring the song home, and "Jeremy" (A man reminisces about the problems of a boy that killed himself in class.)

There.

Ruby (Don't Take Your Love to Town) -- Kenny Rogers
Maria -- Rage Against the Machine

ozoneocean
Only Gary Jule's version of Mad World. That's depressing.

I'd have said Michael Andrew's version. Only a song that emo could end a movie like Donnie Darko.

'Sing' by the Dresden Dolls. The lyrics in themselves aren't too bad, but the way they're sung...it just breaks your heart.

anybody ever listen to the Unbelievable Truth they so depressing its beautiful, especisally forget about me :)

I vouch for "Hurt" by Nine Inch Nails. Johnny Cash's cover version was pretty depressing too for totally different reasons.

Oh and who can forget Eric Clapton's "Tears In Heaven"?

I'm going to go with "Yesterday" by The Beatles. Now, maybe that's just because that was the only really "depressing" song I listened to after my first real breakup, but to me that's what depression really feels like.

I don't agree with most of these. Yes, they have some depressiveness in them, but most of these are songs they are so sad they simply are pretty and by that they have some sort of 'hope' in them that makes me feel good.

If there was to be a depressive song it must be from Radiohead. Something like Karma Police has the same effect I just descriped, but Paranoid Android hasn't. That's just the most deperessive a song can get. Especially in combination with the video clip. (still it's of very great value). If I look back at my own 'depressive fase' (wearing only black, hating the world, only staying inside) I adored 'Micro Cuts' by Muse. The ending is so powerful that it isn't depressive at all, but that edited over-the-top opera-like singing of Matthew "I've seeeeeeeeeeeeeeeeeen what you're dooooooooiiiing to meeeeeeee! Destrooooyyiiiing puppet striiiings to our sooooouuls" makes me shiver. Jack of Jill's 'When Angels Fuck and Devils Kiss' and 'Star No Star' aren't that happy either. And ofcourse Cranberries - Zombie.

Mark
I vouch for "Hurt" by Nine Inch Nails. Johnny Cash's cover version was pretty depressing too for totally different reasons.

Yes, that NIN-song is also pretty depressive. The Cash-version however makes me feel real good again, I don't know what is is man.

The Verve - The Drugs Don't Work was chosen by some sort of poll by the BBC I believe, a while ago. I don't agree with that, again yes the song is sad, but it's BEAUTIFUL! It doesn't have that depressive effect on me.

Also, "I'm Dying" by Vast is pretty depressing.

Somewhere Over The Rainbow - Eva Cassidy - It's a simple guitar melody that sounds sweet but sad and it's compounded by the fact that she had a such a sad death.

Agnus Dei (Platoon Theme)- Samuel Barber - The movie was sad and the melody makes you consider throwing yourself off a cliff.

Nothing In My Way - Keane - Sad piano ballad, video makes is sadder though...

Runaway Love - Ludacris feat. Mary J. Blidge - Really sad R&B, but in my opinion, that's ALL Mary J. Blidge makes.

Donne le moi temps - Jenifer - Really really sad french song.

The Sixth Station - Sprited Away - The music scene where she tells Haku his name always makes me cry a little.

Destiny - Megumi Hayashibara & Seki Tomazaku(sp?) - The words are really sad plus in the anime both characters commit suicide.

Bitter Cry - Haibane Renmei - this one really, really got to me but that's not hard :P

Something Which I Can't Forget - Haibane Renmei - rather touching but depressing

Will of the Heart - Bleach - also depressing.

Here's my list of most depressing songs ever.

Luka- Susanne Vega
Everything I Touch, I Break- Stabbing Westward
Miss Misery- Elliot Smith
Blasphemous Rumors- Depeche Mode
Anything by Nick Cave

And for the win... the most depressing song ever...

Seasons in the Sun- Terry Jacks

My biggies:

"Glycerine" by: Bush
"Come Downstairs and Say Hello" by: Guster

Less for their actual content, but for their connection to the point in my life I was at when I first heard them.

Joy Division - Day of the Lords

Ouch, it really hurts in my depressive-brain-organ (yes, I actually have one of those)

There are some songs I will always hear and feel sad while listening to them.
Eleanor Rigby
She's Leaving Home
Golden Slumbers (into) Carry That Weight
A Day in the Life

-The Beatles. I don't know why Golden Slumbers into Carry That Weight depresses me, but it does. And A Day in the Life. Dunno why it upsets me, but there ya' go.

Goodnight Saigon by Billy Joel. I CRY when I listen to it. Every time.

I'll be Home for Christmas

Somewhere from West Side Story

The Sound of Silence
A Most Peculiar Man
Richard Corey
Dangling Conversation
Bookends
Sounds of Old People Talking (or something similar)
-Simon and Garfunkel

That's all I can think of now on a random perusal of my iPos contents

Twin
'Sing' by the Dresden Dolls. The lyrics in themselves aren't too bad, but the way they're sung...it just breaks your heart.

Truce hits me harder than Sing.

johnny cash - hurt

Twin
'Sing' by the Dresden Dolls. The lyrics in themselves aren't too bad, but the way they're sung...it just breaks your heart.

that song is too cheerful for me... but good choice.

I second Puff The Magic Dragon, simply because that is more likely to be the first sad song you'll ever hear in your young life. That's what happened to me. At first I thought I was hearing an enjoyable kid's song. But after hearing it a few times and then making an active effort to make out all the lyrics (I was pausing the tape and writing on my notepad), I was hit with the awful truth.

Heh. When I was a wheeee little lad I'd just cry when I heard Puff the Magic Dragon. :(

Stupid song!

This Brilliant comic by Lothar reminds me of it actually and I think he did it better.

Better than Puff the Magic Dragon? Your standards are a bit fuzzy.

Anyways, no matter how much I changed, I never ever treated my dog any differently. I can't see how anyone could, and I would look down on anyone who did, and feel no sympathy for him/her.

Who Wants to Live Forever - Queen
...or at least it bums me out when I listen to it. XP

mlai
Better than Puff the Magic Dragon? Your standards are a bit fuzzy.

Anyways, no matter how much I changed, I never ever treated my dog any differently. I can't see how anyone could, and I would look down on anyone who did, and feel no sympathy for him/her.

I feel sympathy for the dog, which is what I felt for the tragic dragon, not the careless boy.

That queen song is VERY depressing... You're right Sarah.

One of my favorite depressing songs, especially considering the context around it, is Elliot Smith's "Kings Crossing".

"nuthing left" by Insane Clown Posse ! its a good song !

btw, that comic was a true story, so i guess i'm a tottal Bastard, i've been dreaming about that dog coming back to life for the past ten years now ...