Saddest music you've ever heard

A Case Of You-Joni Mitchell
This one has that beautiful Joni Mitchell folk blues feel to it, with the melancholic undertone of Mitchell's crooning. Impossibly beautiful and sad.

With Or Without You-U2
Title says it all, really. Anthemic, epic, yet evocatively emotional. Theme song for anyone who's ever loved someone they can't get. Bonus: Joey and Rachel's theme song from Friends!

The River-Bruce Springsteen
One of the best lines in any song, and saddest.
"Now those memories come back to haunt me/they haunt me like a curse/Is a dream a lie if it don't come true/Or is it something worse?"

And Johnny Cash's cover of Hurt, of course. If you haven't heard it i recommend you do. The song weeps with quiet emotion and sadness at a life wrecked by neglect and pride, anchored by Cash's voice of bottomless gravity. He owned the song, which says a lot for a cover.
 
hmmm what about the whole Black album by Metallica...since it was a tribute to Burton.

maybe nothing else matters too?
 
And She Said - Quasimodo
i heard this song live at esplanade on the same day me and my girlfriend broke up. it was one of the most depressing day of my life. suffered at work that night. heh.
and she said? "i wanna be with you, but not now". coincidentally what SHE said. somewhere along that line.

aaand of course,
Graduation - Vitamin C

Knockin' on Heaven's Door. doesn't matter who sings it. covers or whatever, it's still a sad song to me.

and some others that i can't think of right now.
 
the story behind poison's "every rose has it's thorn" is that the poison lead singer called his girlfriend one night and over the phone he heard a male cough in the background

maybe it didn't occur to him that it was possible given the fact that she was a STRIPPER...
 
Interesting posts from you peeps here :)
Pardon the long list!

Perfect Day - Lou Reed (first time I heard it was....*surprise surprise* a mediacorp...or was it SBC local drama that featured this song in a scene where one of the character was killed when his car crashed into a tree *lol* But during that time damn drama to me cos I was much younger mah)
http://www.youtube.com/watch?v=nCymRC7cZTk

Scarborough Fair - Simon And Garfunkel (loved the age-old ballad since the 17th century)
http://www.youtube.com/watch?v=XEhAXQ5QQzs

Get Me Away From Here, I'm Dying - Belle and Sebastian (The light-hearted acoustic strumming contrasts the sad lyrics, making it even more impactful...)
http://www.youtube.com/watch?v=3T6vGCbhsDA

Manhattan Skyline - A-ha
http://www.youtube.com/watch?v=YZqcmZqKY9s

Comforting sounds - Mew
http://www.youtube.com/watch?v=AAT9GiVU6g0 (I love the vid!)

Chop Suey - System of a down (especially the latter parts of the song)
http://www.youtube.com/watch?v=mdRd3k4CIAg

More commercial stuff:
You're beautiful - James Blunt
Somebody - Depeche Mode (everytime listen to it, damn yearning for a partner *lol*)

Instrumental:
Sleepwalk - Santo & Johnny (the very first time I hear it was from the movie, La Bamba in where news broke out that Ritchie Valens was killed in the plane crash...that music, coupled with the scene, moved me to tears)
http://www.youtube.com/watch?v=JJR-qdwxYOg
 
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