This list is in no particular order, however I do think that Johnny Cash's Hurt is the Number One Saddest Song of ALL TIME.

Seriously, I spent a bit of time working on this list, raked through my music portfolio, cried a little, now I have a sore throat from trying not to cry. Damnit, why do I have to be emo?

Still, I know there is a lot missing from this list, but I couldn't be bothered to make it longer tonight. Perhaps I will work on it more later.

Hurt – Johnny Cash
I don't know what it is about this song, but it just rips the heart from my chest and stomps on it. Easily the saddest vocals.

He stopped loving her today – George Jones
He loved her until he died, obsessed till the end. Sucks to be him.

All My Trials – Anita Carter
Your mom is dying. What's sadder? Youtube it. Haunting song.

Not Pretty Enough – Casey Chambers
One woman looses her sense of self-worth.

Am I not pretty enough
Is my heart too broken
Do I cry too much
Am I too outspoken
Don't I make you laugh
Should I try it harder
Why do you see right through me

I live
I breathe
I let it rain on me
I sleep
I wake
I try hard not to break
I crave
I love
I've waited long enough
I try as hard as I can

Smoke Rings in the Dark – Gary Allen
He can't make you love him. So he takes up smoking.

Ships that don't come in – Joe Diffie
A sad toast.
So here's to all the soldiers
Who have ever died in vain
The insane locked up in themselves
The homeless down on Main
To those who stand on empty shores
And spit against the wind
And those who wait forever
For ships that don't come in.

Leaving October Behind – Sons of the Desert
Dad lives on with his young daughter after his wife dies, dreads october because that's when she died.

My December – Linkin Park

and i give it all away
just to have somewhere to go to
give it all away
to have someone to come home to

Don't Close Your Eyes – Kieth Whitely
A woman who closes her eyes when you fuck, and images you are someone else. So he begs her to let it be him, just once. Now that's messed up.

I'm No Stranger to the Rain – Kieth Whitely

But when I get that foggy feeling
When I'm feeling down
If I don't keep my head up, I may drown
But it's hard to keep believing
I'll even come out even
While the rain beats your hope in the ground
And tonight it's really coming down

Enough said.

Cold, Cold Heart - Hank Williams
I tried so hard my dear to show that youre my every dream.
Yet youre afraid each thing I do is just some evil scheme
A memory from your lonesome past keeps us so far apart
Why cant I free your doubtful mind and melt your cold cold heart

I'm So Lonesome I Could Cry – Hank Williams
Did you ever see a robin weep
When leaves begin to die
That means hes lost the will to live
Im so lonesome I could cry

Please Remember Me – Tim McGraw

She left him, and all he wants is for her to remember him. Please. Pretty please.

Alone But Not Lonely – Mary Chapin Carpenter
One very, very lonely girl. I, too, wish I could be alone but not lonely.
Everyday on the street I study their faces
The ones who rush on through the crowd
Towards their own quiet worlds, their separate places
Somewhere I'm never allowed

The End of my Pirate Days – Mary Chapin Carpenter
This song helped me through a tough break-up. Well, not really, it made me weep buckets.
The night is soft and silent, new moon at my door
There's nothing near as quiet as the light I'm looking for
And last time that it appeared he was lying next to me
Last time I felt this near to whispered ecstacy

And those who need adventure, they can sail the seven seas
And those who search for treasure, they must live on grander dreams

We rose and fell just like the tides, he filled my heart and soul and I
Buried all my dreams for someone else to find in my pirate days

This world is kinder to the kind that won't look back
They are the chosen few, among us now, unbowed somehow
And one day he turned to me, and before I took one breath
I knew I would only see his shadow in what light was left

And those who need adventure, they can sail the seven seas
And those who search for treasure, they must live on grander dreams

And if I've seen his face since then, it's only been in dreams my friend
Since I came to the end of my pirate days
And if I've called his name since then, it's only been in dreams my friend
So I came to the end of my pirate days

Someone else's Prayer – Mary Chapin Carpenter
She travels the world to get away from him, and always his memory follows her. At least she finds closure at the end without having to die. Only song on this list with a happy ending.
Where do shadows fall when there's only light
Why'd you follow me halfway 'round the world tonight
What I'd give right now not to even care
And then this could be someone else's prayer

And on a sleepless night by St. Stephen's Green
Oh I turned and tossed with my Irish dreams
And when the morning shone through the burned off mist
I could sense you still just as close as this
Just as close as lips brush against a cheek
It's your voice I hear and it's your name I speak
But when I look around there's no one there
How I wish you were someone else's prayer

And now the twilight comes as a silent guest
And of all its gifts I like stillness best
Except for tin roof rains that commence with spring
It's a lullaby when that tin roof sings
Now you can look for me on the streets of Rome
Or in Dublin town but I've gone back home
I would always be just a stranger there
And now you're free to be someone else's prayer

Rhythm of the Blues – Mary Chapin Carpenter
He just keeps coming back, to rip her heart out anew.
I want a place to call my own, where you have never been
I wanna look around and know you won't be coming back again
On some pretense paper-thin that I can see right through
You come and go baby, like the rhythm of the blues

Burned in my Mind – Sons of the Desert
A man turns to alcoholism to get over being left. She says she still loves him, but does it make a difference if they can't be together?
Johnny Walker's on the table
He tends to soothe since you're unable
Day after day, after day
Johnny's walking all over me
Slowly gaining control of my destiny

But it's tried and it's true
And there's nothing I can do
But make it through everyday

You make the pain go away
When you say
You still love me
I don't know why I can't let go
I'd like to say goodbye

But you're burned in my mind
You're burned in my mind

Ghost of a Good Thing – Dashboard Confessional
He loves her, and she's off chasing what could have been. This guy has a really haunting voice, but he is no Johnny Cash for making you feel it.

The Storm – Garth Brooks
Yeah, I know Garth Brooks is a douchenozzel but this song is good stuff.
He left her. It sucked. She found out why, and it was even worse. Ignorance is bliss.
The door it slammed like thunder and the tears they fell like rain
And the warnings from her family whirl like a hurricane
She's drowning in emotions and she cannot reach the shore
She's alive but can she survive the storm

I fall to Pieces – Patsy Cline

Beautiful voice. He left her, told her to get over it, yet he still hangs around with her friends. That bastard.
I fall to pieces,
Each time someone speaks your name.
I fall to pieces.
Time only adds to the flame.

Streets of Heaven – Sherrie Austin

Maybe it's because I am a new mom, but this song tears the heart from me. I weep. I literally weep.
So tell me: what do you need her for? Don't you know one day she'll be your little girl forever. But right now I need her so much more. She's much too young to be on her own; Barely just turned seven. So who will hold her hand when she crosses the streets of Heaven?

Nothing Compares to You - Sinaed O'Conner
No words to describe. No words can describe. Listen, and you will know. That is all.

No Surprises - Radio Head

I'll take a quiet life
A handshake of carbon monoxide

A Change Is Gonna Come - Sam Cooke

He knows he's gonna die. Maybe it's better that way after all.
I was born by the river in a little tent
And just like the river, I've been running ever since
It's been a long time coming
But I know a change is gonna come

It's been too hard living, but I'm afraid to die
I don't know what's up there beyond the sky
It's been a long time coming
But I know a change is gonna come

I go to the movie, and I go downtown
Somebody keep telling me "Don't hang around"
It's been a long time coming
But I know a change is gonna come

Then I go to my brother and I say, "Brother, help me please"
But he winds up knocking me back down on my knees

There've been times that I've thought I couldn't last for long
But now I think I'm able to carry on
It's been a long time coming
But I know a change is gonna come

Back to Black – Amy Winehouse
He goes back to her, and she goes back to black. She has an amazing voice, but she is so fucked up.

Anyone Who Had a Heart - Dionne Warwick

He's a low down, dirty rotten... MAN.
Every time you go away, I always say
This time it's goodbye , dear
Loving you the way I do
I take you back, without you I'd die dear
Knowing I love you so

Silent All These Years - Tori Amos
What better way to describe a past rape than with silence?

The Captain - Casey Chambers

She is one sad little pirate, with a soul-wrenchingly sad voice. You be the Captain, and I be no one.

Broken Wing – Martina McBride
Spousal abuse leads a woman to jump to her death.

Independence Day – Matina McBride

Spousal abuse leads a woman to burn herself and her drunken husband to death leaving behind a young daughter.

Concrete Angel – Martina McBride

Child abuse. Sad, sad.
Bearing the burdon of a secret storm,
Sometimes she wishes she was never born;

Through the wind and the rain,
She stands hard as a stone in a world that she can't rise above;
But her dreams give her wings and she flies to a place where she's loved.

Concrete Angel

Somebody cries in the middle of the night,
The neighbors hear but they turn out the lights;
A fragile soul caught in the hands of fate,
When morning comes it will be too late.

Through the wind and the rain,
She stands hard as a stone in a world that she can't rise above;
But her dreams give her wings and she flies to a place where she's loved.

Concrete Angel

A statue stands in a shaded place,
An angel girl with an upturned face;
Her name is written on a polished rock,
A broken heart that the world forgot.

Alone Again (Naturally) - Gilbert O'Sullivan
His bride-to-be stands him up at the alter, so he kills himself. Damn, it really sucks to be him. It's such a jaunty little tune until you hear the lyrics.

Gloomy Sunday – Billie Holiday
Man, doesn't her voice just cut right through the bullshit and bore into your brain?

Jeff Buckley – Hallelujah
I'm not sure why this song is so haunting, maybe it's the instrumentals, maybe it's the vocals, but it causes a distinctly uncomfortable burning sensation behind my eyes.

Cry Me a River - Julie London.
Wow. What a voice. Great revenge song for after a break-up.

Last Kiss - Pearl Jam

Everybody Hurts – REM

Tears in Heaven – Eric Clapton

My Heart Will Go On - Celine Dion