Let's hear your nominees. I'll put a few out there:
Hurt (any version is equally affecting; here's a
duet with Bowie, here's
Kermit)
Why it's the saddest song: "What have I become, my sweetest friend? Everyone I know goes away in the end ..."
Strike against it: Reznor got rich, famous and happy with music like this. Kinda undercuts the whole premise of Emo misery.
The Only Answer (ignore the video, just listen to the music)
Why it's the saddest song: "Five years in the wrong I am assured, my name to you is just another word." Great zinger for a lost love, you gotta admit. We've all been there.
Strike against it: Maybe a little too up-tempo to be the bummer music of all time.
The Ballad of Hollis Brown
Why it's the saddest song: Well, it does describe a seven-person murder/suicide from the most sympathetic possible perspective. Points for weirdness at least.
Strike against it: Maybe too horrifying to be strictly sad.
Rollin' By
Why it's the saddest song: The death of an entire town: "Me I stand here at the last filling station, while the wind moans a dirge to a coyote's cry."
Strike against it: How sad are we supposed to get about the passing of a community?
I could go on, but I'll stop there for now. So far I think I'd have to give the title to
Hollis Brown, even if it is a little bit grotesque.
Hooahguy 04:19 07-10-2009
ok, people will hate me for it, but id say, as the saddest song that i listen to, is
The Outlaw Torn, by Metallica.
now, there are many ways to interpret the song. i think that its talking about a man who years for his love but then finds out that she left him.
thats just what i think.
i also like
Second Chance, by Shinedown
pevergreen 05:13 07-10-2009
Get out of myspace - pure pwnage
CountArach 05:43 07-10-2009
Pretty much anything by Anberlin. That stuff depresses me... Yet I'm going to go and see them next month...
I really dig that cover by Dolbro Dan, I don't really like Bob Dylan at all, but that cover made me like the song now.
Louis VI the Fat 05:53 07-10-2009
Born in the USA - Bruce Springsteen.
Why it's the saddest song:
Ballads are never sad. Songs need tension, ambiguity. The pumping drums, that keyboard melody, the vocals shouted at the top of his lungs both perfectly capture the theme of the lyrics and contrast with them. The nuance of the lyrics are in great contradiction to the unsubtleness of the music. It is a sad song, introverted. The lone thoughts of a lone man, abandoned. The words ought to be mumbled by an embittered man, alone on his porch. Uttered by that drunk you walked past earlier that day, avoiding eyecontact.
Strike against it: Like a video of Neda, unbearable to sit out. You want to cast your eyes downwards, avoid the shame, the intrusion.
The greatness is the ambiguity with the bombastic stadium rock anthem music.
Legosoldier 06:18 07-10-2009
Nebel, by Rammstein
Why it's the saddest song:
"The last kiss was so long ago, the last kiss, he does not remember it anymore..." The song is about the death of a loved one, and what is ironic about this is the title; when you flip it backwards, it says leben, which means life.
Strike against it:
Till Lindemann's gruff voice doesn't exactly match the mood of the song, but even then, it still sounds pretty great.
Originally Posted by Louis VI the Fat:
Born in the USA - Bruce Springsteen.
Why it's the saddest song:
Ballads are never sad. Songs need tension, ambiguity. The pumping drums, that keyboard melody, the vocals shouted at the top of his lungs both perfectly capture the theme of the lyrics and contrast with them. The nuance of the lyrics are in great contradiction to the unsubtleness of the music. It is a sad song, introverted. The lone thoughts of a lone man, abandoned. The words ought to be mumbled by an embittered man, alone on his porch. Uttered by that drunk you walked past earlier that day, avoiding eyecontact.
Strike against it: Like a video of Neda, unbearable to sit out. You want to cast your eyes downwards, avoid the shame, the intrusion.
The greatness is the ambiguity with the bombastic stadium rock anthem music.
Louis, I'll see your "Born in the USA" and raise you another Springsteen song, "Jungleland". Probably my favorite song of all time, and is one of the very few songs that still gives me shivers when I listen to it.
Why it's the saddest song:
Excellent portrayal of life wasted in the 70s, and still a great depection of how street/gang life is
just so stupid even now. Great piano riff and sax solo as well.
Strike against it:
Bit lengthy, really. Also, keep in mind that this was the period of time when Springsteen was at his most bombastic, music-wise, if you're not into that.
~~~~~~~~~~~~
"
Landslide" by Fleetwood Mac
Why it's the saddest song:
Moving guitar work. In addition, the lyrics to a point deal with the ever-present problem of aging and looking back at everything and how it's all piled up on you at once.
Strike against it:
I suppose it's not sad so much as melancholy and reflective.
~~~~~~~~~~~~~
"
American Pie" by Don McLean
Why it's the saddest song:
Yeah, I know,
that one. But my interpretation of the song is McLean's viewing of the 60s as an outsider; watching as everything he holds to dear to him crashes and burns (in some cases, literally) in the madness that was the later part of the decade. The final verse is just apocalyptic.
Strike against it:
Despite the overall theme of the song, parts of it are pretty up-tempo. In addition, it loses points in the same way that "Hurt" did - the song is now a staple of classic-rock radio, sharing airtime with the same artists that killed the good ol' days. -edit- Also, for some inexplicable reason, Madonna did a cover version of this that was so abysmal it detracted from the power of the original. Weird Al's version didn't help either, but at least that was funny.
Well... supposedly more than a hundred people, including the composer himself, committed suicide right after listening
"Gloomy Sunday", "The Hungarian suicide song". It was banned during the thirties because of that....
https://www.youtube.com/watch?v=4WBZwLkvpFI
Wouldn't that make it the saddest of all time?

. Personally I find, 'sad',
Auf Asche by Franz Ferdinand. I also love
Moonlight Sonata, which is melancholinc in it's own way.
PS: Sorry for any messiness with my post. I had to do all the coding manually... Remind me to change my posting window options. Oh and sorry for not using the format hehehe I'm in a hurry right now.
LeftEyeNine 08:37 07-10-2009
Probably there are dozens I'll be able to recommend however momentarily one pops up.
Goran Bregovic - Aven Ivenda
It has such an embracing atmosphere that I remember my little brother as numb as dead, lying on the carpet as I started to play that song.
Banquo's Ghost 13:47 07-10-2009
I fear I am about to end this debate right here. Once an Irishman enters the fray of laments, the conversation is over.
Danny Boy, as sung by the wondrous voice of Eva Cassidy.
Why it's the saddest song?
You need to ask? The sorrow of a nation that lost her children. The tragic loss of the songstress. It's an Irish lament.
Strike against.
None at all. If you are not weeping your heart out through this song, you surely lack poetry of the soul.
I've been trying to think of songs that I found to be very sad.
The one I can think of that always kinda gets me, mainly because I am a hugely sentimental weenie, is
Here's to the Night by Eve 6. It always drags up memories of friends, places, experiences that I know I'll never see again.
Another one that's kinds corny with somewhat of the same effect is
See you when you get there by Coolio.
The next one I can think of is the song from the
final scene of Gladiator. Perhaps the visuals and backstory have something to do with it, but nevertheless I found it to be very sad and final.
The songs are somewhat "sad" by themselves, perhaps it's more of the personal twist that applies directly to me that I would associate them as opposed to them just standing alone without perspective.
"Szomorú Vasárnap" or "Gloomy Sunday"
Just listen to it. It drives you insane.
..or off a bridge/cliff
Tristuskhan 18:24 07-10-2009
Last Kiss by anyone who's ever covered it. I have to change the radio station whenever that thing comes on or I'll drive myself off a bridge just to end it.
He ain't heavy, he's my brother, by the Hollies.
They played it at my buddy's funeral years ago. He and his girlfriend were killed in a car accident and the funeral was for both of them at the same time. Some funerals are light hearted, some are some are even fun; this one was just a great big kick in the nuts. It's been years and I still can't hear that song without losing it.
Maybe it's not a sad song, really, but it's sad for me.
Hosakawa Tito 01:52 07-11-2009
Pretty tough to top Danny Boy.
However, this song,
Teach Your Children , has special meaning to me. I just started my midnight shift at the jail and was relieved from my post to take an outside phonecall in the watch-commander's office. My mother called to tell me Dad had just passed away. I held up okay till on the drive home that song came on the radio. Then I cried like a baby the rest of the way....
johnhughthom 02:49 07-11-2009
https://www.youtube.com/watch?v=5Qepn6PN8Y4
Williams Last Words by The Manic Street Preachers.
From their recent album (great by the way, first Manics album I've bought in 14 years). Though the band have denied it, it's hard to see it as anything other than a suicide note from Richey Edwards who disappeared in 1995. It's sung by Nick Wire, probably the band member closest to him, and his lack of singing ability somehow add to the song.
Samurai Waki 03:23 07-11-2009
Lament by Arcana. Every time I listen to it, I look back on my entire life, and know that eventually that I will be unable to escape my own death.
Lord Winter 06:54 07-11-2009
Solider of Fortune by deep purple and the other bands that have covered it. Simple and somber with beautiful mellotron. I'm not a huge fan of Coverdale's voice but the lyrics and instruments more then make up for it. Also Epitaph by King Crimson, more somber simple music, excellent vocals and the mellotron back ground all expressing cynicism and hope tied into one song. Surely the invention of the mellotron was one of the greatest in all of human history.
Banquo's Ghost 12:41 07-11-2009
Originally Posted by
Hosakawa Tito:
However, this song, Teach Your Children , has special meaning to me. I just started my midnight shift at the jail and was relieved from my post to take an outside phonecall in the watch-commander's office. My mother called to tell me Dad had just passed away. I held up okay till on the drive home that song came on the radio. Then I cried like a baby the rest of the way....
That touched me deeply,
Hosa.
I feel I should share something personal in return. "
I hope you meet again" by the Saw Doctors evokes the heartbreak and loss of the Troubles. My priest, knowing how much I liked the band, had it played at my daughter's funeral and now it is both unbearable and strangely comforting listening to it play.
Forgive the idiot video - it's the only version I could find.
Hosakawa Tito 13:09 07-11-2009
Originally Posted by
Banquo's Ghost:
That touched me deeply, Hosa. 
I feel I should share something personal in return. "I hope you meet again" by the Saw Doctors evokes the heartbreak and loss of the Troubles. My priest, knowing how much I liked the band, had it played at my daughter's funeral and now it is both unbearable and strangely comforting listening to it play.
Forgive the idiot video - it's the only version I could find.
That is a very moving folk song. While sad, it also gives one comfort and hope for the future. Thank you for sharing that and the personal story behind it.

For me, music is the auditory touchstone in our lives that we use to associate with life's ups & downs.
I recall watching a tv program on Irish folk bands a while back. One of the musicians interviewed had a great insight on the tradition and evolution of their music. I don't remember the exact wording, but to paraphrase, " The victors write the history, but the vanquished write the songs."
KukriKhan 13:53 07-11-2009
Ballad of The Green Beret - SSG Sadler & R. Moore.
Why it's the saddest song: Soldiers dying in foreign lands. Wives, mothers & gf's losing their men.
Strikes against it: It's so unabashedly patriotic that it provides fodder for much and many
parodies.
pevergreen 14:11 07-11-2009
I just remembered the song that makes me cry every time I hear it.
You may know it as the song from that ad with the balls bouncing down the street.
The cover of
heartbeats by Jose Gonzalez (
https://www.youtube.com/watch?v=s4_4abCWw-w). The original is terribad IMO, but this cover makes me cry every time.
Ah...damnit I'm listening to it now because I got the link...and the tears start a'flowing.
edit: its probably only sad because its so very meaningful to me.
Pannonian 14:32 07-11-2009
And the band played Waltzing Matilda
Why it's the saddest song: "And the band played Waltzing Matilda / As the ship pulled away from the quay / And amidst all the cheers / The flag waving and tears / We sailed off for Gallipoli / ....So they gathered the crippled, the wounded, the maimed / And they shipped us back home to Australia / The legless, the armless, the blind, the insane / Those proud wounded heroes of Suvla / And as our ship pulled in to Circular Quay / I looked at the place where me legs used to be / And thank Christ there was nobody waiting for me / To grieve, to mourn, and to pity / But the band played Waltzing Matilda / As they carried us down the gangway / But nobody cheered / They just stood and stared / Then they turned all their faces away
Strike against it: Some of the details weren't quite accurate, and Bogle felt it went on too long. However, there was a stunned silence, followed by standing applause when it was first performed in public.
Reverend Joe 19:00 07-11-2009
I don't think this can top some of the songs already posted here (that Gallipoli one is pretty rough) but I'll still post
"Monday, Monday" by the Mamas and the Papas to top some of the poppier songs.
Why it's the saddest song: it's probably the most depressing pop song ever; the Mamas and the Papas had a knack for mixing sad lyrics with appealing music, but this probably tops all their other efforts. It's a song about someone (the sex is never identified) whose partner breaks up with them on one of the best Mondays of their life -- so now, "whenever Monday comes, you can find me cryin' all the time..."
Every freakin' Monday. Not a holiday or a month, but a day of the week -- that sucks.
Strikes against it: The fact that it sounds like a poppy love song means that quite a few people will probably miss the lyrics, or at least their meaning, which is sad becuase it beats the hell out of every Emo song ever.
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