Most. Depressing. Pop or rock song. Ever.

I have to go with Lou Reed’s Perfect Day.

Every Rose Has its Thorn by Poison
Something I Can Never Have by Nine Inch Nails
My Immortal by Evanescence
Landslide - Fleetwood Mac

A few months ago I heard the Beatles song For No One for the first time. It’s about a guy whose girlfriend just doesn’t love him anymore. It bummed me out for about two hours after hearing it.

That song was also recorded by his son, Rufus Wainwright.

The most depressing pop song is Bonnie Raitt’s “I Can’t Make You Love Me” about a woman (or man) coming to terms with the fact that her feelings are unrequited. Excerpts below (warning: get your hanky ready):
Here in the dark
in these final hours
I will lay down my heart
And I’ll feel the power
but you won’t…
Morning will come
and I’ll do what’s right
just give me till then
to give up this fight

::sob::

Complete lyrics

The Smiths: Heaven Knows I’m Miserable Now…

I was happy in the haze of a drunken hour
But heaven knows I’m miserable now
I was looking for a job and then I found a job
And heaven knows I’m miserable now
In my life
Why do I give valuable time
To people who don’t care if I live or I die?
Complete Lyrics

Well, if you want to bring up The Smiths, there’s plenty of material. How about “Asleep,” a nice little suicide number:

Sing me to sleep
Sing me to sleep
And then leave me alone
Don’t try to wake me in the morning
'Cause I will be gone
…Don’t feel bad for me
I want you to know
Deep in the cell of my heart
I really want to go
There is another world
There is a better world
Well, there must be
Well, there must be…

But of the songs that made the charts in the US, I’d have to agree with "Ode to Billy Joe"

Don’t Take the Girl by someone who’s name escapes me. That might be too country for the list, though.

What was the name of the song about some shoes a kid wants to bury his mother in? That’s most depressing song ever.

Dylan’s Ballad of Hollis Brown. In fact a good chunk of The Times They are a Changing is depressing. When I was in college I stopped playing it at 3 am since it made me want to jump out the window. (The Lonesome Death of Hattie Carrol ain’t too cheerful either.)

Wildfire is pretty depressing.

Neil Young: Here’s a song that will bring you right down. It’s called “Don’t Let it Bring you Down.”

Everything But The Girl’s Me and Bobby D is pretty bad, involving abuse/etc.

I don’t need no arms around me
And I don’t need no drugs to calm me.
I have seen the writing on the wall.
Don’t think I need anything at all.
No! Don’t think I’ll need anything at all.
All in all it was all just bricks in the wall.
All in all you were all just bricks in the wall

(smooth — albeit creepy — seque into…)

Goodbye cruel world,
I’m leaving you today.
Goodbye, goodbye, goodbye.
Goodbye, all you people,
There’s nothing you can say
To make me change my mind.
Goodbye.

Alone Again Naturally is just about as depressing as it can get:

And then it gets depressing.
*Seventeen * is pretty wrist slashingly depressing

However I have to add * Arms of an Angel * by Sarah Mclachlan:

Life sucks, kill yourself and maybe things will get better (only more beautifully said)

I came in here to say Brick as well. Man it hurts to listen to that song.

Also, Tears in Heaven by Eric Clapton

Cat Steven’s Father & Son is another song of non-connection:

How can I try to explain?
When I do he turns away again.
And it’s always been the same, same old story.
From the moment I could talk I was ordered to listen
Now there’s a way and I know
I have to go away away.

ABBA’s Knowing Me Knowing You:

Walking through an empty house, tears in my eyes.
Here is where the story ends. This is good-bye.
Knowing me, knowing you, there is nothing we can do.
Knowing me, knowing you, we just to face it, this time we’re through.

Pink Floyd’s The Wall. The. Whole. Freakin’. Album. Both disks. And the feature film. And the concert film. Jeez, what were these guys tryin’ to do, pump up the national suicide rate to win a bet or somethin’?

That would be Tim McGraw.

Well, let’s not forget Leonard Cohen’s Dress Rehearsel Rag.

On the subject of father/son missed connection, there’s Barry Manilow’s song Ships.

Most of this is subtle, finely-tuned, relationship depressing. You want cranked up, heavy metal depressing, try D.O.A. from Bloodrock, about a plane crash victim bleeding out on the ground after the wreck.

The one I came in to mention. Wow, what a downer.

Pretty much anything from Simon and Garfunkel’s “Sounds of Silence” album is pretty depressing, too.