I forgot one in my earlier posting haste.
“Shes’ Already Made Up Her Mind” by Lyle Lovett
Two immediately come to mind:
“Yesterday” by The Beatles. Can’t believe nobody mentioned this, unless I missed it.
“Fast Car” by Tracy Chapman. What a sad song about someone trying to escape a horrible life for something better only to wind up right back where they started.
I’ve come up with a few more…
For a band who’s every single song has made me cry, Anathema.
I have particular favorites though…
Anathema -A Fine Day to Exit
" "Deep
" "Panic
" "Everwake
" "Inner Silence
" "Parisienne Moonlight If your going to download any, get this one
" "Release
" "Anyone Anywhere
REM - Loosing My Religion (That’s a given)
Switchfoot - You
Duran Duran - Come Undone
Duran Duran - Ordinary world
Diana Washington - What a Difference a Day Makes
Jars of Clay - Lift Me Up
Fred Astaire - Cheek to Cheek (From the Green Mile soundtrack)
Massive Attack - Teardrop
Stutterfly - Gun in Hand
Chobits - Opening Song
It’s an anime, and for some reason this song really gets to me.
Maybe it has to do with the show, not too sure…
I can’t believe no one has mentioned NFB.
Shannon by Henry Gross. Even if it is about a dog.
How many votes have been cast for Danny Boy now? Three? I’ll make it four. Or whatever.
L’un Vers L’Autre from Les Miserables always gets to me. It has since I went through a French-English dictionary and figured out what some of it meant.
I also cry every time I hear The Lost Chord [arthur sullivan] or Emma’s last melody in Jekyll and Hyde:
You are free now
You’re with me now
Where you’ll always be
Sorry Trancey, it’s Dinah Washington.
Songs To Aging Children Come - Joni Mitchell
Don’t Let It Bring You Down - Neil Young
nobody’s mentioned Neil?
A Better Place To Be - Harry Chapin
Desperado - The Eagles
This thread has been done many times before… but…
-Another vote for Danny Boy
-Another vote for A Gentle Fall of Rain from Les Miz, along with the death of Fantine, and the reapearrance of Fantine’s ghost (“Monsieur I bless your name” “I am ready Fantine” “Monsieur lay down your burden” “at the end of my days” “You’ve raised my child in love…”)
-Puff the Magic Dragon
-Where have all the flowers gone?
-But the hands down saddest song ever written, at least when heard in its correct context, is Oh Lord, I’m on my way, the finale from Porgy and Bess. The irony is that it’s this incredibly upbeat triumphant music, but it’s triumphant because poor Porgy (who has no legs) is wheeling his way in his cart out of Catfish Row to go to New York (which is described as “way up north, past the customs house”) to find his true love, Bess. And he’s all hopefuly and happy, and the music is all excited and happy, and of course you just know that he’s never going to make it. Gut-wrenching.
Another vote for Jeff Buckley’s “Lover, You Should’ve Come over” and for Tracey Chapman’s “Fast Car.”
I’m surprised no one’s mentioned anything my Ryan Adams or his former band, Whiskeytown. “Jacksonville Skyline,” “Sit and Listen to the Rain,” “Come Pick Me Up,” and “Harder Now that It’s Over” are all incredibly morose.
“Jacksonville Skyline,” actually, reminds me of “Fast Car” in the way it captures the narrator’s inability to change his situation in life. The saddest songs, for me, are the ones about dashed hopes.
Joy Division Isolation “I’m ashamed of the things I’ve been put through; I’m ashamed of the person I am”
Belly Low Red Moon “Now I’ve got strong arms, strong arms for a skinny girl, and I say ‘He belongs to me’”
Slint Good Morning, Captain “I miss you”
Cat Power Moonshiner “When the bottle gets empty, then life ain’t worth the drown”
Nina Simone Strange Fruit “Southern trees, bearin’ strange fruit”
Big Star Big Black Car “Driving in my big black car, nothing can go wrong”
Nick Drake All My Trials “But it’s too late, my friend, too late but never mind”
Neutral Milk Hotel Two-Headed Boy Pt. 2 “And in my dreams you’re alive and you’re crying, as your mouth moves in mine, soft and sweet, Rings of flowers round your eyes and I’ll love you for the rest of your life”
- Tim Buckley Song to the Siren (the version on Starsailor)
This Mortal Coil does a very pretty version of this song, but after hearing Tim’s Starsailor version their’s doesn’t even seem sad at all. Tim Buckley had the greatest voice of any singer, it has to be heard to be believed.
“Here I am, here I am, waiting to hold you”
Nightime: Strange Fruit is certainly a great song. But it’s usually associated with Billie Holiday (although writen by Lewis Allen for her).
For Nina Simone (who at 80+ when I saw her at the Scnitz here in Portland was still stomping) and a sad rendition I would say her “I Put A Spell On You” is Earthshaking and sad in it’s desperation. Her cover of “I loves you Porgy” is pretty damned good too.
I have to add yet another vote to Jeff Buckely’s*“Lover, You should’ve come over”*. Gets to me every time. He had the voice of an angel.
Then there’s “Oh Death” from the the O Brother, where art Thou soundtrack.
“Wichita Lineman” by Glenn Campbell.
“And I need you more than want you and I want you for all time
And the Wichita lineman is still on the line…”
sigh
and “Wildfire” by Michael Martin Murphy. Saddest “girl-dies-in-blizarrd-looking-for-her-horse” song I’ve ever heard. 
Cocteau Twins - Spooning Good Singing Gum, Eggs And Their Shells
Lisa Fischer - Ruler Of My Heart
John Mayer - Cavatina (theme from Deer Hunter)
Elvis Costello - Couldn’t Call It Unexpected No. 4
Peter Gabriel - Flotsam And Jetsam
Sam Stone - By John Prine
Actually, of the top-20 saddest songs, I think about 7 or 8 of them would come from John Prine. “Angel From Montgomery”, “Hello in There”, “Far From Me”, “Paradise”…
Wow! Two references to Porgy And Bess, but neither one mentioned the truly sad Where is Brother Robins?, sung by the chorus about a fisherman lost at sea in a storm, and the really gut-wrenching My Man’s Gone Now, sung by Robins’ widow. “Ain’ no use a listnin’ for his tired footsteps climbin’ up the stair.” Now, that’s sad.
Kern River - Merle Haggard
Pancho and Lefty - Townes Van Zandt
Please Please Please Let Me Get What I Want - Smiths
This Is Not A Rebel Song - Sinead O’Connor
A Rainy Night In Soho - The Pogues
I Love - Tom T. Hall
So Cruel - U2
The Only One - Billy Bragg
Tank Park Salute " "
This Womans Work - Kate Bush
Apron Strings - Everything But The Girl
Requiem - Mozart
And a very depressing song I’ve been listening to lately:
The Old Main Drag - The Pogues
Synopsis:16 yr old boy heads to London with only “…a fiver in my pocket…” gets swept into a life of being a drug addicted “rent boy.” The last verse of the song goes
“Now I am lying here, I’ve had too much booze/I’ve been spat on and shat on and raped and abused/I know that I am dying and I wish I could beg/For some money to take me from the old main drag”
G.
There are very few things that I regret having done. Having said that, I sincerely regret doing a search for the lyrics to “Padraic My Prince”.
Jesus Christ
I second Coldfire’s selection of Pink Floyd’s The Gunner’s Dream, and am quite frankly amazed that that seems to be the only Floyd song picked. C’mon, The Wall should have been packaged with lithium pills for convenience!