Put “Papa’s Roses” by Pat Benatar and “Little Did She Know (She Kissed a Hero)” by Kristy Jackson on the list. Just thinking about the Kristy Jackson song (it’s about 9/11) makes me tear up.
I was a kidlet when “Wildfire” (about the horse?) came out and it made me cry. And I’m not into horses, or animals in general, if you follow me. I still could get misty-eyed in the right frmae of mind. And when my girlfriend (now wife 
) broke up with me, I listened to Blues Travelers’ “Alone” about 1000 times a day. It was cathartic to cry like that. The song itself is sad in tone, but, man, if you’re already in the dumps, look out!
And I didn’t write down the poster, but to whoever listed REM’s “Everybody Hurts”, it is not a sad song. Granted, it’s not a bouncy sing-a-long like “Stand” or “Shiny Happy People”. It’s meant to give comfort to those who are already sad, you know, everybody hurts sometimes, everybody cries. You’re not alone! Feel better! You’re just human too! It’s kind of sunk into pathetic pop culture scorn, but I still love that song.
I agree, Les Mis is full of sad songs. My favorite DVD is the Dream Cast concert. I would also nominate Empty Chairs at Empty Tables as another good, sad song. Especially if sung by Michael Ball.
Another vote for Eric Clapton’s “Tears In Heaven”…
If the starting lyrics is…“Would you know my name if I saw you in Heaven?”…knowing that he is asking this question posthumously of his deceased 2 year old son (I believe his name was Connor who died tragically) in fear of being permanently disconnected from him physically, mentally and spiritually is quite a dosage of depression that Eric easily summed up in this tune.
Hopefully, a fear that none of us has to experience firsthand…
rackensack, “It Makes No Difference” is one of the saddest songs I’ve ever heard, but I had forgotten about it until you mentioned it.
Also had to add Sinead O’Connor’s “Nothing Compares 2 U” and Tom Waits’ “Invitation to the Blues.”
I can’t beleive no one’s mentioned…
Amazing Grace.
Or maybe Somewhere, Out There
Good one! I’d also add Your Latest Trick from the same album.
Also, I Am Stretched On Your Grave as performed by Dead Can Dance.
And when I was a kid, in the Reagan era, Russians by Sting used to truly depress me…
Mr Reagan says we will protect you
I don’t subscribe to this point of view
Believe me when I say to you
I hope the Russians love their children too
Noah’s Dove by 10000 Maniacs , I was going thru a difficult time when I first heard it.
Yetticus, Clapton’s son was indeed named Connor. He died after falling out a 49th-story window in his mother’s Manhattan apartment.
Pretty much of the eels’ library is pretty depressing/sad. There are also some killer sad songs on the new Belle & Sebastian album. For example, from “Lord Anthony”:
“Tasting blood again… at least it’s your own.”
and
“You may as well take one in the guts – it can’t get worse than this.”
vunderbob – “I Don’t Like Mondays” is my favorite song in the world. Never heard it described as sad, but I can easily see how.
I’m also on board with “Puff, the Magic Dragon”. Jackie Paper dies, dammit. That’s not a happy thing.
Time by The Alan Parsons Project.
The Pretenders - I’ll Stand by You
The Blantyre Explosion always makes me cry. So does Two Little Boys by Rolf Harris, even though it has a happy ending.
“Why” Roger Whittaker…I know, I’m old
'Scuse me, Rawkstah, but Jackie Paper doesn’t die. He GROWS UP. The song is about the loss of innocence - how Jackie grew up and didn’t believe in things like dragons anymore.
Check snopes.com if you don’t believe me.
Presley made a balls of it, Willie Nelsons recording is by far the best.
Another for saddest is Bill Withers " Lean on Me"
…and nobody has mentioned “Words” The BeeGees
Pearls - Sade
My girlfriend died at about the same time as Eric Clapton’s son and someone bought be Tears in Heaven on 12in.
It still makes me cry - but I still don’t think of it as a sad song.
It’s very, very beautiful.
Chalk up a “me too” for that one.
I want to add:
The duet by Sheryl Crowe and Emmylou Harris on “Juanita”, from a Gram Parsons tribute album, and “River of Tears” by Eric Clapton.