I am making a CD of heartbreaking songs

[HornGrandioso]

So far:

John Lennon - Mother (there is no sadder song)
James McMurtry - Rachel's Song
Ryan Adams - Dear John
Townes Van Zandt - Waitin Round to Die
Roy Orbison - Crying
U2 - Love is Blindness

...don't ask me why I get off listening to utterly hopeless sad songs, just suggest.

And don't try and slip in a song that ends on a happy note!

 

[HornGrandioso]

Oh man, adding another Roy Orbison song: It's Over.

First line: "Your baby doesn't love you anymore..."

Musical masochism at its finest.

 

[Third Coast]

Bonnie Raitt - "I Can't Make You Love Me"

 

[El_Oso]

George Jones - "He Stopped Loving Her Today"

 

[kangsta]

Gary Jules- Mad World

 

[El_Oso]

Johnny Cash - Hurt

 

[NatChampUT]

Blink 182- Adam's song
Donnie Hathaway- A song for you

 

[kangsta]

Ben Lee - Sleepwalking

 

[halsteadfrost]

Last Kiss

There's an original version by J. Frank Wilson and the Cavaliers and it was covered by Pearl Jam.

 

[Horn89]

Patty Griffin, "Nobody's Crying"

 

[TXgrl222]

Desiree- Kissing You

It's more of an urban song compared to what's been listed, but it gets me everytime. From the Romeo and Juliet soundtrack.

 

[soonerinatlanta]

You've never heard of it but I'll offer

East River Pipe - Druglife

The lyric that gets me:
If it comes down to the drugs or you
Baby, we're through

 

[addison4ya_28]

Brand New - Limousine

And here is the story its based on...

Lyrics

 

[Macanudo]

U2 - All I want Is You

 

[Soul Glo]

sinatra-send in the clowns

 

[chillywillywall]

george strait- cheyanne

 

[schnarkle]

Do You Realize - Flaming Lips

 

[El_Oso]

Neko Case - Maybe Sparrow

 

[Horn37]

Old 97's - Salome, No Mother
Uncle Tupelo - Still Be Around
The Replacements - Here Comes A Regular
Sufjan Stevens - Casimir Pulaski Day

 

[HenryGandorf]

my favorite sad song is "suffering" by satchel, from the beautiful girls soundtrack.

jeff buckley probably belongs somewhere on your cd. "last goodbye" maybe.

 

[l00p]

The Cure - Untitled (that is the name of it, last track on Disentigration

Depeche Mode - Somebody

Daft Punk - Something About Us (theme from Interstella...found on Daft Club)

Sade - Love is Stronger Than Pride

Cocteau Twins - Wax and Wane (very moody, many of their tracks)

Scorpions - Lady Starlight (go ahead, laugh. It's on the Animal Magnetism lp)

 

[Mr. Orange]

Ben Folds - Fred Jones

 

[Crusher X]

R.E.M. - Sweetness Follows . A very haunting song. Its on "Automatic for the People".

 

[rhorn27]

Ray Lamontangue
Empty

 

[rage-a-holic]

This Mortal Coil - It'll End in Tears

 

[DCLonghorn]

Can I slit my wrist now??

 

[Phil Conners]

Ben Harper - Another Lonely Day

 

[hullabelew]

Broken Fingers by Sam Baker. His left hand was destroyed in a terrorist explosion. He was almost killed and lost virtually all of his hearing. Along the lines of John Prine.

 

[PanzerDSS]

In reply to:

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[Mageeman]

Personally I think "Cigarette" by Ben Folds is even sadder that the successive Fred Jones, but both are great songs.

Here's some gold old folk songs that always me think about my past and other things.
Goin' Away - Utah Phillips (I really recommend this one and probably my favorite song)
Girl From the North Country - Bob Dylan/Johnny Cash or any good cover (Mojave 3 does an awesome version)
Boots of Spanish Leather - Bob Dylan