I think alot of Silverchair songs are pretty depressing.

"Don't Think Twice, It's Alright" is a song Bob Dylan wrote about leaving his female-friend in the middle of the night and in his voice in this song, you can really hear how he hurts. It seems everyone in the world has covered this song, Radiohead, Peter, Paul and Mary, and a few more whose names I cannot think of right now, but the original is far superior. One verse goes like this though:

"I'm walking down that long, lonesome road, babe
Where I'm bound, I can't tell
But goodbye's too good a word, gal
So I'll just say 'Fare thee well'
I ain't sayin' you treated me unkind
You could've done better but I don't mind
You just kinda wasted my precious time
But Don't Think Twice, It's Alright"

I'm a HUGE Dylan fan, I've seen him 3 times which is every time he's been remotely near in the last 7 years or so, each time with my pops, but his new rockin' style lacks all truly creative energy he once had, he's a man on decline, sadly. However, another two of his very best songs, but that are both depressing as hell is "Percy's Song" and "The Lonesome Death of Hattie Carroll." "Percy's Song" is about his buddy going to jail for 99 years for "manslaughter, in the higest of degrees" when he was in a car accident claiming the lives of 4 others. "The Lonesome...." is about an Aristocrat going free for Murder One, when he slays his maid out of fury from a dinner discussion, and does it at dinner. The way these two songs are juxtaposed on the Dylan box set is pretty damn depressing as well. I presume it to be intentional, but I wonder...

Send in the Clowns-

That's the most depressing song I've ever heard in my entire life.

However, I also think it's an incredibly beautiful and well done, depending on Artist singing it. It has amazing flow.

Always,
Jess

That reminds me of Bruce Springsteen's entire "Nebraska" album. Brilliant, but it can make you want to crawl under your bed and not come out for a few days. "Johnny 99" is especially depressing, about a man who is laid off of his job and in a drunken rage shoots a clerk at a convenience store. When the judge sentences him to 99 years in prison, the man answers:
"Now, judge, judge I got debts no honest man could pay
The bank was holding my mortgage,
they were going to take my house away.
I'm not saying that makes me an innocent man,
but it was more than all this that put that gun in my hand.
Your honor, I do believe I'd be better off dead,
And if you can take a man's life for the thoughts that's in his head
Then sit back in that chair and think it over, Judge, one more time,
And let 'em shave off my hair and put me on that execution line."

I'm listening to it right now. I think I'm going to fix a drink. :(

oh most definitely the depressing-est song I know is "Stan" by Eminem.

When I was in college and grad school I often felt as though I was living in a Stevie Nicks song...most often "Sometimes it's a Bitch" or "Two Kinds of Love" ("And don't you know/as you walk on by/the great temptations never really die")

One of the songs that brings back happy memories is "A Land Down Under" by Men at Work...heehee every time I hear it I remember dancing to it on a coffee table at the Delt house during Rush. And for driving on the 405, there's no other song than "Red Barchetta" by Rush. Different songs bring back different memories, I guess.

Poetry Man, Phoebe Snow:
The Other Woman, Nina Simone
Next Lifetime, Erykah Badu
Easy to be Hard, Movie Soundtrack from "Hair"
One Mo 'Gin, D'Angelo

Ok, I mentioned this once before-
"Something Vague" by Bright Eyes will make you kill yourself. I'm talking, slit my wrist with a fork/hang myself by my shoelaces b/c it's so sad.

Pink Floyd
 

No one mentions Pink Floyd? No one makes music more depressing than Pink Floyd. Try The Gunner's Dream off of their most depressing album, The Final Cut.

floating down through the clouds
memories come rushing up to meet me now
in the space between the heavens
and the corner of some foreign field
i had a dream
i had a dream
goodbye max
goodbye ma
after the service when your walking slowly to the car
and the silver in her hair shines in the cold november air
you hear the tolling bell
and touch the silk in your lapel
and as the tear drops rise the meet the comfort of the band
you take her frail hand
and hold on to the dream

a place to stay
enough to eat
somewhere old heroes shuffle safely down the street
where you can speak out loud
about your hopes and fears
and what's more no-one ever disappears
you never hear their standard issue kicking in your door
you can relax on both sides of the tracks
and maniacs don't blow holes in bandsmen by remote control
and everyone has recourse to the law
and no-one kills the children anymore
and no-one kills the children anymore

night after night
going round and round my brain
his dream is driving me insane
in the corner of some foreign field
the gunner sleeps tonight
whats done is done
we cannot just write off his final scene
take heed of his dream
take heed

Canadian singer Michelle Wright's "He Will Be Sixteen" about a woman (girl, really. According to the lyrics, she's a high school student) who gave up her baby for adoption.

Chorus is:

"He would be sixteen
The son she never knew
It hurt so much to give him up
But what else could she do
He would be sixteen "

No one's mentioned "Cat's In The Cradle" by Harry Chapin. That song always makes me feel sad.

'She Just Wept' by Star Sailor
'Lighting Crashes' by Live
'Brick' by Ben Fold Five

pretty much any song by dashboard confessional makes me want to slit my wrists ;)

"Free Bird" is another sad song.

The Dangling Conversation by Simon and Garfunkle. The words are really pretty sad, I think.

And how the room is softly fading
And I only kiss your shadow
I cannot feel your hand
You're a stranger now unto me
Lost in the dangling conversation...

Sounds too much like two people growing farther and farther apart.:(

One Sweet Day - Mariah Carrey and Boys II Men

This Used to Be My Playground - Madonna (even more depressing when you watch the end of A League of Their Own and the song's playing)