For me, a toss up between Concrete Blonde’s Joey and Evanescence’s My Immortal.
Of course pop music is one thing. For true, mind-numbing, soul-crushing sadness, nothing beats a classical piece like Adagio for Strings…
If we’re going the classical route, Abinoni’s Adagio in G Minor literally hits every sad note in the book.
Since I had to look it up anyway, Into The West by Annie Lennox.
Johnny Cash - Hurt. I think this is a contender, especially considering the context.
In the same vein (and with the same name), Christina Aguilera - Hurt.
Nobody’s mentioned Elanor Rigby by The Beatles. Also Queen’s Save Me and U2’s Love Is Blindness.
I once saw this song reduce a room of fifty-eight newly recovering male addicts to blubbering messes when it was played after a lecture on the importance of communication. It was a bit lugubrious but I suspect, for them, refreshingly cathartic.
My earliest sad songs were sung to me by my grandmother and still can move me to tears - for mysterious strangers! Babes in the Woods and Red Wing.
Jeez, Grandma!
Most of my sad songs have been mentioned already, but these haven’t:
“The Flowers Of The Forest”, cause I did some research about what it’s really about. John McDermott sings a wonderful cover of it, but there are alternate lyrics.
“Too Ra Loo Ra Loo Ra (That’s An Irish Lullaby)”, not because I’m Irish but because my mom passed a couple of years ago.
“When I Had You” by Jerry Jeff Walker
Carly Simon’s - That’s the Way I Always Heard It Should Be.
The last verse never fails to make me tear up. I guess that says a lot about me.
“When I am Laid in Earth” by Henry Purcell (from "Dido and Aeneas)
“Not All My Torments”, also by Henry Purcell
“Flow my Tears” by John Dowland
And, of course, Israel Kamakawiwo’ole’s “Over the Rainbow/ Wonderful World” medley, which we played at my mom’s funeral.
I was going to mention “She’s Leaving Home” and forgot to.
As for Carly Simon, I recommend Better Not Tell Her
“My Father” by Judy Collins. I understand she wrote it as a tribute to her own blind father. When I first heard it I thought of my own father, who was not blind and actually doing quite well at the time. I don’t know; it’s just one of those songs…
God Damn The Sun by Swans Or Failure, by same.
Sam Stone by John Prine
First Christmas by Stan Rogers
I guess there’s a fine line between “sad” and “repulsive.”
I’ve always had a soft spot for “My Sister” by Tindersticks:
I will follow you into the dark by Death cab for cutie. Mainly because of the video http://www.youtube.com/watch?v=jEGXU773tTM
my other is hello by evanescence http://www.youtube.com/watch?v=F9x4wmsPTlk
Expecting To Fly by Neil Young when he was in Buffalo Springfield.
Although it’s not about death or other nasties, it’s a heartbreakingly sad song about broken love. The orchestration by Jack Nitzsche is very effective.
Maybe not the saddest song per se, but I’ve seen it described as the saddest of all love songs, and I concur:
Not familiar with that one, but another that fits the thread’s title - and your description of “The Kids” - is Lou Reed’s “Street Hassle”. Just thinking of the strings music opening the song is enough to raise the pollen count in the room … if you catch my drift. The whole song kills.
If you haven’t heard the Alison Krauss version, it really deserves a listen. The whole album is a melancholy treat.
Her song “Standing Knee Deep in a River” is another really sad song about friends and love lost.
In a close second place for me, Ferron’s “Ain’t Life a Brook”.A song about reconciling your life with your ex after a breakup and watching the facade of “let’s still be friends” slow fade away with that person.
[QUOTE=Ain’t Life a Brook]
And just the other day
I got your letter in the mail
I’m happy for you, it’s been so long
You’ve been wanting a cabin and a backwoods trail
And I think that’s great…me…
I seem to find myself in school
It’s all Ok, I just want to say
I’m so relieved we didn’t do it cruel
But ain’t life a brook
Just when I get to feeling like a polished stone
I give me along drawn look
It’s kind of a drag to find yourself alone
And sometimes I mind
Especially when I’m waiting on your heart
But life don’t clickety clack down a straight line track
It comes together and it comes apart.
[/QUOTE]
But first place is a song that gets me every goddamn time. Melissa Etheridge’s "Tuesday Morning". The lyrics are about Mark Bingham, the gay man who with 3 others helped take down Flight 93 on 9/11. But crossed with those lyrics are the story of a country that marginalized people based on their sexuality. It’s probably because that’s very personal for me that it gets me even now as I’m typing this.