Hackensack, by Fountains of Wayne, the saddest song about unrequited love ever (yes, my first girlfriend to break my heart was an actress, why do you ask?)
Call To Heaven, by Patty Smyth, about a firing squad in WWI, the song is just haunting.
not exactly the saddest song i know, but most of those have been mentioned already in this thread (my vote goes for Wreck of the Edmund Fitzgerald). this is an old song by Paul Evans named “Hello, this is Joannie.”
it is kinda corny, kinda fun, and plenty sad...but the best part is that if you message Paul Evans on youtube or via email, he will probably message you back as he is still very active online despite being well into his 70s.Since there are dozens of sites where one can read the whole lyric of a million songs, what is the purpose of barring more than 5 lines here?
[channeling Mom]
If your friends jumped off a cliff, would you jump too? 
[/cM]
Well, if “Old and Wise” by Alan Parsons doesn’t tug your heartstrings, I don’t know what will.
Those dozens of sites are violating copyright. The people who run SDMB don’t want to do that.
I remember this song reducing my mother to tears when I was a child. I didn’t understand. I thought it would be wonderful to “turn around and be grown”. I have a son. Now I understand.
Am surprised nobody’s voted for this one yet: Peter, Paul and Mary’s Leaving on a Jet plane (written by John Denver).
Already I’m so lonesome
I could cry
So kiss me and smile for me
Tell me that you’ll wait for me
Hold me like you’ll never let me go
*
“The One You Really Love” by The Magnetic Fields
Hard to see where the financial loss to the author comes in. I’d think it would be the other way round. In any event, thanks for editing my posts to keep me out of jail…
would anyone linking to a lyrics site, or youtube video also be putting SDMB in jeopardy?
How has there been no mention of Jeff Buckley?
“Lover, You Should Have Come Over”
Also:
Mason Jennings - “Rebecca DeVille”
There are some great sad songs here. I’ll be wallowing in it tonight I guess.
My nominees:
Leonard Cohen: “One of Us Cannot Be Wrong”.
It’s got a plot like “Something About Mary”.
Gordon Lightfoot: “If You Could Read My Mind”
Falling out of love and unable to communicate the pain and sense of loss.Crosby, Stills, Nash and Young: “Wasted on the Way”
It’s just about the passing of time and how we waste so much time on the unimportant things.The last time through, when they switch from “Time” to “Love” in the lyrics always tugs at my heart and makes me wonder if I’ve been a good enough son, husband and friend.
That’s a little surprising; I’ve always seen that song as about, oh, 80% comedy.
Not *you “out of jail,” but Cecil. (Okay, jail unlikely, but a site shutdown would not be unprecedented). And, yes, links to just about anything are fine. (They link to other *sites, hence the name).
Not sure why you feel a need to get rather whiny about simple and easy-to-follow rules.
There’s always Pete Seeger’s Where Have All the Flowers Gone?
Here’s Peter, Paul, and Mary’s version of Pete’s song. They add two verses, to make explicit the circle which Pete just leaves for the listener to figure out.
I’ve always found Bruce Sprinsteen’s Brilliant Disguise terribly sad.
Me too. Another song written during the throes of divorce. I think Springsteen is somewhat under-rated as a songwriter…he’s done a lot of stuff that reaches me. I don’t know if he personally did the arrangement for “I’m On Fire”, but between the instrumentation and vocals, I’m filled with a feeling of unfulfillable longing.
The Last Song - Elton John
According to Wikipedia, “The song tells of an estranged father coming to terms with the sexuality of his gay son, who is dying of an AIDS-related illness.” I’ve had quite a few close friends die from that.
Girl I’m Gonna Miss You - Milli Vanilli
It was played at the funeral of my first high school love, who committed suicide at the age of 19. Since her funeral, I haven’t heard that song in its entirety.
Empty Chairs at Empty Tables - from Les Miserables
Around the same time in high school, I went to see my first musical. This was one of the songs I cried to that day. And when I saw the film version a couple of years ago, I teared up again.