I wish someone would Unbreak Toni Braxton’s Heart because it puts me in a blue mood every time I hear it.
And I’ll fifth Bonnie Raitt’s I Can’t Make You Love Me. Heart wrenching.
Alison Krauss’s It Doesn’t Matter is good for putting me in a funk even though it’s short on lyrics. The melody and her haunting voice just sound so lonely.
I will have to say Bonnie Raitt’ s – I Can’t Make You Love Me…
it always brings a tear to me eye…and when I hear her sing it or even think about it I get all choked up…
excuse me I need a minute… 
If someone made a gravelly-voiced acoustic version of Herman’s Hermits’ Mrs. Brown You’ve Got a Lovely Daughter, I wonder if it would be perceived as earnest or camp.
I’m surprised no one’s mentioned Sarah McLachlan I Will Remember You.
Another one is I Wish by Carl Thomas:
I can’t even think about, let alone listen to ‘Honey’ by Bobby Goldsboro. My mother used to cry when she heard it (she said it reminded her of her mother who had died). My mother died in 1975 when I was 12 so now every time I hear the song, I cry too.
‘My Heart Will Go On’ only makes me cry when I see the Celine Dion video with it. It’s the scene with the old couple clinging to eachother in bed and kissing good-bye while water surges around them that gets me.
Sniff, sniff
Inspired by a similar thread on the Unaboard, I created a playlist of Sad Songs from my media files. Here it is:
Valentine - Old 97s
New Favorite - Alison Krauss
All My Love IS Gone - Lyle Lovett
Blue Eyes Crying in the Rain - Willie Nelson
Dancing With Tears in My Eyes - Old 97s
Distantly in Love - Jimmy Buffett
Haunt Me - Countney Fairchild
He Stopped Loving Her Today - George Jones
How Do You Tell Someone? - Cowboy Mouth
I Can’t Love You Anymore - Lyle Lovett
Imaginary Love - Rufus Wainwright
I Should’ve Known Better - Nickel Creek
I Want Love - Elton John
It Ought to Be Easier - Lyle Lovett
I Wish I Felt Nothing - The Wallflowers
Jagged - Old 97s
Lonely In Love - Lyle Lovett
Reasons Why - Nickel Creek
Sabra Girl - Nickel Creek
She Never Knew Me - Don Williams
She’s Already Made Up Her Mind - Lyle Lovett
She’s Leave Me Because She Really Wants To - Lyle Lovett
Silver Wings - Merle Haggard
Some Broken Hearts Never Mend - Don Williams
Sorry - Courtney Fairchild
These Reminders - Max Stalling
This Train Don’t Stop There Anymore - Elton John
Three Cigarettes in an Ashtray - k.d. lang
Valentine’s Day - the Help
Wavin’ My Heart Goodbye - The Flatlanders
What A Crying Shame - The Mavericks
What Bothers Me Most - Waylon Jennings
“I Can’t Make You Love Me” by Bonnie Raitt is my number two contender. What a great song!
But I’m surprised that no one mentioned The Dance by Garth Brooks. To wit:
First time I heard that was two days after breaking up with a girlfriend I’d been with for two and a half years…really hit home at that point in my life.
My (not-very-definitive-at-all-due-to-my-relative-lack-of-exposure-to-music-before-the-mid-80’s) list:
Total Eclipse of the Heart- Bonnie Tyler
“Once upon a time I was falling in love,
Now I’m only falling apart…
Nothing I can do, a total eclipse of the heart…”
I Let Love In- Nick Cave
“Well, I’ve been bound and gagged and I’ve been terrorized
And I’ve been castrated and I’ve been lobotomized
But never has my tormentor come in such a cunning disguise–
I let love in.”
A Letter to Elise- The Cure
“Oh Elise it doesn’t matter what you do
I know I’ll never really get inside of you
To make your eyes catch fire
The way they should
The way the blue could pull me in
If they only would
If they only would
At least i’d lose this sense of sensing something else
That hides away.”
A Night Like This- The Cure
“It goes dark… it goes darker still- please stay!
But I’m watching like I’m made of stone as you walk away…”
Strange Attraction- The Cure
“I’m sorry, blame infatuation,
Blame imagination,
I was sure you’d be the one, but I was wrong,
It seems reality destroys our dreams,
I won’t forget you…”
Painters- Jewel
"Until one day the rain fell as thick as black oil,
And in her heart she knew something was wrong.
She went running through the orchard, screaming,
“No God, don’t take him from me,”
But by the time she got there,
She feared he already had gone.
She got to where he lay,
Water-colored roses in his hands for her.
She threw them down, screaming,
‘Damn you, man, don’t leave me with nothing left behind
But these cold paintings, these cold portraits to remind me!’
He said, “Love I only leave a little, try to understand.
I put my soul in this life we’ve created with these four hands.
Love, I leave, but only a little,
This world holds me still.
My body may die now, but these paintings are real.”
La de di, la de di, la de di, de di."
Snif Brings a tear to my eye every time. Okay, hundreds of tears.
Foolish Games (Album Version)- Jewel
“You’d teach me of honest things,
Things that were daring, things that were clean,
Things that knew what an honest dollar did mean.
So I hid my soiled hands behind my back
Somewhere along the line, I must have gone off-track with you.
Excuse me, think I’ve mistaken you for someone else…”
Creep- Radiohead
“When you were here before,
Couldn’t look you in the eye,
You’re just like an angel,
Skin makes me cry.
You float like a feather
In a beautiful world…
You’re so f*cking SPECIAL!
I wish I were SPECIAL!
But I’m a creep,
I’m a weirdo.
What the HELL am I doing here?
I don’t belong here.”
My pick would be Janis Ian’s Jesse as sung by Joan Baez.
*Jesse come home, there’s a hole in the bed
Where we slept; now it’s growing cold.
Jesse your face, in the place where we lay
By the hearth, all apart, it hangs on my heart
And I’m leaving the light on the stairs
No I’m not scared; I wait for you
Hey Jesse, it’s lonely, come home.
*
“When She Loved Me” by Jessie the Singing Cowgirl
“For No One” by The Beatles
“Thorn Tree In The Garden” by Derek and The Dominos
“Girl From The North Country” by Bob Dylan
Al Green’s cover of “How Can You Mend a Broken Heart?”
Such a wrenching experience that this song should only be heard after taking Zoloft.
I’ve always found Harry Nilsson’s “Without You” to be wonderfully depressing:
<i>Can’t live, if living is without you
Can’t live, can’t give anymore</i>
I may have the title wrong - that’s what the MP3 came off kazaa titled as, but who knows how accurate that is.
She sees him laying in the bed alone tonight
The only thing a touching him is a crack of light
Pieces of her hair are wrapped around and 'round his fingers
And he reaches for her side, for any sign of her that lingers
And she says you are not alone
Laying in the light
Put out the fire in your head
And lay with me tonight
One of them bullets went straight for the jugular vein
There were people running , a flash of light
Then everything changed
Nothing really matters in the end you know
All the worrys sever
Don’t be afraid for me my friend, one day we all fall down forever
Shodan hit it on the head with Nothing Compares 2 U. Damn cried my eyes out over that one today. Dittos as well for Fire & Rain and I can’t make you love me.
Actullay being single ALL love songs are depressing to me right now, the top three being “Suddenly” by Billy Ocean, “Because I love you” by that other guy and “Still Ray” by Raphael Sadiq
teleute12 [sup](there are 11 other posters by that name ?)[/sup]
Without you - Nielson is far more tragic then most people realise.
The song was credited as being written as a group effort by the UK band Badfinger, though the truth was that is was mostly the work of Pete Ham who was a depressive and very cut up over the breakup with his then girlfriend.(Tom Evans was the cowriter)
Pete Ham had many serious depressive episode, not helped by wrangling over royalties between the band and a crooked management, and when Harry Neilson made the song a worldwide smash, this made the arguments even more bitter.
Pete never really got over that breakup and committed suicide, the band split up, reformed some time later, only to have Tom Evans committ suicide in 1983 the same way as Pete.
The song title is literally true.
A couple obscure songs:
Sarah, from Bob Dylan’s album Desire
Dancing with tears in my eyes - Ultravox’s album Lament
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I can’t believe it took this long for someone to mention The Smiths!! Just about any one of their songs would qualify IMHO.
A few others:
“In the darkened underpass
I thought Oh God my chance has come at last
But then a strange fear gripped me
And I just couldn’t ask”
There is a light and it never goes out - Who doesn’t have regrets about a missed opportunity?
Jeff Buckley’s
Forget her is another good example.
“But don’t fool yourself
She was heartache from the moment that you met her
Now my heart is frozen still as I try to find the will
To forget her somehow…
She’s somewhere out there now.”
It’s a bit out of left field, but I’ve always found They’ll Need a Crane, by They Might Be Giants, to be one of the saddest songs there is. The lines: ‘I’m just tired/ And I don’t love you any more’, delivered without much of any kind of emotion, always just tears me up.
It’s Too Late by Carole King
Not even sure if it is a love song, but All the things she said makes me think of my ex in a love song kind of way