“World Coming Down” by Type O Negative
I’ll second the nomination of Red Water (Christmas Mourning) by Type O
And to end this mindnumbingly long post i’ll nominate “Northern Lad” By Tori Amos. This song remindes me of that man who broke my heart. Sigh
No offense, torie but I believe the moderators prefer if you don’t post whole lyrics of songs on the boards. Copyright issues, y’know.
You can post portions of lyrics or links to pages with full lyrics, though. May want to try that next time.
Sorry to be the local whinge.
whoops…Didn’t think of that. Sorry. Feel free to edit, Mods. Here are the links.
World Coming Down by Type O Negative
http://www.lyricsondemand.com/t/typeonegativelyrics/worldcomingdownlyrics.html#07
Red Water by Type O negative
http://www.lyricsondemand.com/t/typeonegativelyrics/octoberrustlyrics.html#06
Northern Lad by Tori Amos.
http://www.lyricsondemand.com/t/toriamoslyrics/northernladlyrics.html
Creep, by Radiohead have been the most depressing song I’ve heard.
She’s leaving home by -you know who, don’t you?- seems pretty sad to me, too.
One song that make my eyes wet (I don’t know if it’s sad, but it works that way for my heart) is Those were the days, by Mary Hopkin. In fact, I can’t explain it.
Good call on Kid Rock there, Horseflesh.
I nominate…
Disappear and Space-dye vest - Dream Theater
A therapy for pain and Timelessness - Fear Factory
To live is to die - Metallica
Tears of Sahara - Tony MacAlpine
-Wish You Were Here - Pink Floyd
Surprised I haven’t seen anyone bring this up yet (unless I missed it). Probably Floyd’s saddest song.
-That’s the Way - Led Zeppelin
Not as well known as their other songs, from the criminally underrated third album.
She’s Leaving Home and Wish You Were Here are winners. I like Radiohead a lot, and while I think Motion Picture Soundtrack is very moving (and it’s not going to bring a smile to your face), it’s not really that depressing. Romeo and Juliet get to be together in heaven, it’s the continuation of Exit Music. It’s not lighthearted, but you can get more depressing than that, with the harp music and all.
Pink Floyd’s Time is about as much of a downer as there is, if you ask me. Tori’s got plenty of sad ones as well… I’d nominate Me and a Gun, but I think that’s more horrifying than sad. Playboy Mommy, maybe, or I Can’t See New York.
Willing to Wait by Sebadoh
Soldier’s Joy by Michelle Shocked
I Married Her Just Because She Looks Like You by Lyle Lovett
Tears in Heaven – Eric Clapton
I always cry when I hear this song.
That’s because it’s also such a very sweet song. Kinda in a similar vein as the “I’d like to teach the world to sing…” song from that old Coca-Cola commercial.
It sounds like something you expect to hear around the campfire rather than from your deathbed.
That song always gave me the creeps as a kid.
Oh God, I can’t believe I forgot Kilkelly!
“Pictures of You” - The Cure
“Estranged” - Guns and Roses (I was too young to understand it the first time I heard it and I still almost cried)
“Bridge” - Queensryche
I find Dream Theater’s Finally Free extremely emotional. Some parts of it are immensely sad, while other parts are actually somewhat uplifting. If the lyrics don’t get you, the sounds of a woman screaming, glass breaking, and shots being fired together with the thunderously heavy, classical-ish bit that borders on cacophonic (though not messy), in there probably will.
Saddest instrumental: Johnny and Santo’s Sleepwalker.
Though not exactly sad, Underworld’s Born Slippy is probably the most depressing song I’ve ever heard, and you don’t even have to hear the lyrics to want to kill yourself listening to it.
“If I Didn’t Care”—The Ink Spots
(Catch the movie reference)
Third time I’ve posted this to similar threads:
My vote is for John Doe No. 24 by Mary Chapin Carpenter. Makes my eyes water just thinking about it.
Lyrics here. It’s based on a true story.
A lot of excellent suggestions already. I’d like to add a few.
Motörhead - 1916
Dire Straits - Brothers in Arms
I’ll think of more later.
Chavardz writes:
> Isreal Kamamawiwo’ole - Somewhere over the rainbow/it’s a
> beautiful world
Trivial nitpick: It’s “Israel Kamakawiwo’ole” and “What a Wonderful World”.
My suggestions are the Eva Cassidy versions of these two songs (although her versions were not a melody of the two). It’s funny - they are supposedly happy songs, but it’s easy to see them as being longing for an unobtainable happiness. I wonder if there’s a rule if a singer does a great version of “Somewhere over the Rainbow” they will die (relatively) young. Eva Cassidy died at 33, Israel Kamakawiwo’ole died at 38, and Judy Garland died at 47.
Pansy Division - Denny
I can’t listen to it most of the time, it depresses me so thoroughly. I changed the artists in the MP3 tags so that it would not come up when I played random Pansy Division.
I concur in both “Honey” and “Seasons in the Sun”. The former is going along just fine as a nice love song retrospective, until suddenly it takes a left turn and you realize the wife had died of some disease or medical problem or some such thing. I rarely get 45’s (well, you know what I mean. I rarely got 45’s) but I went out and bought that one after hearing it.
As for “Seasons in the Sun”, Terry Jacks’ recording was far from the first, let alone best; it was just the most famous. I’ve heard the Kingston Trio version (the first to sing the song using the English translation by Rod McKuen), I have the Nana Moskouri version (VERY sad sounding), and I had at one time the song in the original French (Le Moribund). It is hard to be more sad than a man singing on his deathbed about how hard it is to die and leave behind his friend, father and wife.
Tears in Heaven should make anyone cry. It also has one of the altime best modern recordings (meaning pop music) of someone playing a real guitar.
I’ll add one song from a while ago. The Last Rose of Summer, a Thomas Moore poem put to music by Philip Lawson. It’s last line is “When true hearts lie withered, and fond ones are flown, Oh! who would inhabit this bleak world alone?”
The Irish, ever the optimists. 
Sheesh, no mention of Les Miserables?
“I Dreamed a Dream” quickly prompts some tears and minutes later “Come to Me” has me openly sobbing every time. I’m getting weepy just thinking of it. Something about that parental feeling of leaving a small child behind without you is the most heart wrenching thing I can conceive.
Saddest. Song. Ever. http://icarus.cc.uic.edu/~dmitra1/cometome.shtml
On disc two of Les Miserables “On My Own” and “A Little Fall of Rain” are pretty devastating too.