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Anything by Bobby Goldsboro TrogL Feb 2013 #1
Anything by Madonna rocktivity Feb 2013 #2
hehehehehehe hibbing Feb 2013 #24
Renaissance- "Cold is Being" Doc_Technical Feb 2013 #3
Yeah, but....... lastlib Feb 2013 #67
Daddy's Gone rug Feb 2013 #4
I felt like opening my wrists when this song first came out aint_no_life_nowhere Feb 2013 #5
Concrete Angel - Martina McBride sharp_stick Feb 2013 #6
Love Will Tear us Apart by Joy Division nt NoGOPZone Feb 2013 #7
Leader of the Pack and Teen Angel graywarrior Feb 2013 #8
John Lennon - Mother Tabasco_Dave Feb 2013 #9
Absolutely! Rips my heart & soul out. graywarrior Feb 2013 #12
"Tell Laura I Love Her" by Ray Peterson sinkingfeeling Feb 2013 #10
When I was a little bitty kid in the 50s, this song really made me sad aint_no_life_nowhere Feb 2013 #11
I had never seen a song by him. You know Eileen is an homage, sort of, to him? Here ya go. Honeycombe8 Feb 2013 #30
I Din't Care Anymore by Phil Collins. Mr.Bill Feb 2013 #13
Tommorrow Wendy by Andy Prieboy uriel1972 Feb 2013 #14
here are a few Sad Songs - don't know about depressing but, they are kinda sad Tuesday Afternoon Feb 2013 #15
Try this on: discntnt_irny_srcsm Feb 2013 #48
Billy Jack! here is another one considered to be sad by many (me included) Tuesday Afternoon Feb 2013 #99
I always liked that one discntnt_irny_srcsm Feb 2013 #111
Paper and Pen by Alecia Nugent tg Feb 2013 #16
'Nights in White Satin' by the Moody Blues majorly bums me out Populist_Prole Feb 2013 #17
I think maybe the music from GUNSLINGER GIRL AsahinaKimi Feb 2013 #18
Most anything by BobDylan. RedCloud Feb 2013 #19
"Hurt" as a song is enough ok_cpu Feb 2013 #20
Corgan wrote that shortly after his mother died. Tommy_Carcetti Feb 2013 #62
The back story of that song and album as a whole ok_cpu Feb 2013 #77
Alone Again, Naturally (Gilbert O'Sullivan) Honeycombe8 Feb 2013 #21
I will second that nomination (nt) Jeff In Milwaukee Feb 2013 #32
"Sunny Came Home" by Shawn Colvin rachel1 Feb 2013 #22
Same old lang syne song (Dan Fogelberg) a/k/a I met my old lover in the grocery store... Honeycombe8 Feb 2013 #23
Not Dark Yet - Bob Dylan hibbing Feb 2013 #25
1916 - Motorhead WhoIsNumberNone Feb 2013 #26
Crying (K D Lang) Honeycombe8 Feb 2013 #27
Timothy... he is eaten by fellow miners in a mine collapse XRubicon Feb 2013 #28
So many choices (yours fit the bill, for sure) CreekDog Feb 2013 #29
Michael Gira - "Blind" nomorenomore08 Feb 2013 #31
Joy Division - "Decades" nomorenomore08 Feb 2013 #33
Anything by Harry Chapin, and... ms liberty Feb 2013 #34
My first thought was this song pink-o Feb 2013 #75
Exactly energumen Feb 2013 #91
Yeah, Harry could be a downer. AngryOldDem Feb 2013 #102
Yes, I was thinking the other night that I wish I had a "rewind" function on my life. Still Blue in PDX Feb 2013 #103
Try "The Shortest Story" bobclark86 Feb 2013 #92
Bruce Springsteen - "Racing in the Street" nomorenomore08 Feb 2013 #35
The Clientele - Dreams of leaving AllenVanAllen Feb 2013 #36
Bloodrock - DOA mokawanis Feb 2013 #37
wow lost-in-nj Feb 2013 #90
My brother and I used to play it fairly often mokawanis Feb 2013 #96
It was the 1st thing that popped into my head pintobean Feb 2013 #108
I can't decide between Eleanor Rigby and Alone Again (Naturally). Arkansas Granny Feb 2013 #38
Gloomy Sunday Llewlladdwr Feb 2013 #39
"Last Kiss" southerncrone Feb 2013 #40
Sorry, I'm an old guy: discntnt_irny_srcsm Feb 2013 #41
I think the last one was disqualified after the More Cowbell skit. Neoma Feb 2013 #42
I really like... discntnt_irny_srcsm Feb 2013 #43
Not a depressing song: Neoma Feb 2013 #45
I'm not sure how to characterize this: discntnt_irny_srcsm Feb 2013 #50
I do, too. Still Blue in PDX Feb 2013 #104
If you happen to be... discntnt_irny_srcsm Feb 2013 #110
ah. the guess who. always thought this one by them was very sad - Tuesday Afternoon Feb 2013 #112
"The Christmas Shoes" ... even though I am an atheist ... this gets me every time :( tandot Feb 2013 #44
rare extant recording of an actual castrato datasuspect Feb 2013 #46
Vietnam Deck of Cards datasuspect Feb 2013 #47
I have a few mythology Feb 2013 #49
"I Eat Dinner" by Rufus Wainwright Generic Brad Feb 2013 #51
Neil Young "ON the beach is the all time most depressing song for me Mojorabbit Feb 2013 #52
It really does beat out Tonight's the Night Tom Ripley Feb 2013 #74
I don't know how sad this song is, kentauros Feb 2013 #53
Is That All There Is? Peggy Lee Grammy23 Feb 2013 #54
I'd say the Taxi Driver theme robertkdem1965_h89 Feb 2013 #55
For me, it's "Is it Real" by Yoko Kanno sakabatou Feb 2013 #56
The Way We Were - Streisand. Liberal Veteran Feb 2013 #57
"Happy BIrthday" cliffordu Feb 2013 #58
kern river - merle haggard hopemountain Feb 2013 #59
"Scarecrow" by Melissa Ethridge and when I was younger "Wildfire" by Michael Martin Murphey Behind the Aegis Feb 2013 #60
I don't think I ever heard the song Wildfire without crying. nt Still Blue in PDX Feb 2013 #105
Cats In The Cradle. Alone Again, Naturally. I Am A Rock. Iggo Feb 2013 #61
A few already mentioned here: Tommy_Carcetti Feb 2013 #63
"Happy Birthday To You" always has been, always will be Tom Ripley Feb 2013 #64
Lou Reed "The Kids"... Tom Ripley Feb 2013 #65
To Be Invisible by Gladys Knight Sticky Feb 2013 #66
The Who - "Behind Blue Eyes" lastlib Feb 2013 #68
Ah, I remember listening to this with my boyfriend on his 8-track on our second date. Still Blue in PDX Feb 2013 #109
Mazzy Star - Look on Down from the Bridge Locrian Feb 2013 #69
All Cats Are Grey - The Cure progressoid Feb 2013 #70
"Cat's in the Cradle." NT raccoon Feb 2013 #71
Mad World - Gary Jules kudzu22 Feb 2013 #72
First time I heard it, it was Harry potter movie clips with that song. Neoma Feb 2013 #73
The Wreck of the Edmund Fitzgerald. Manifestor_of_Light Feb 2013 #76
A Song For You mimi85 Feb 2013 #78
Best. Song. Ever. nt Still Blue in PDX Feb 2013 #106
Agreed Sherman A1 Feb 2013 #85
Try "Home From the Forest" by Gordon Lightfoot. Brigid Feb 2013 #79
Tom Waits - A Christmas Card from a Hooker in Minneapolis Beearewhyain Feb 2013 #80
The Lovesong of J. Alfred Prufrock... Wounded Bear Feb 2013 #81
"Ladder Song" by Bright Eyes EastTennesseeDem Feb 2013 #82
Ice Cube--"You Know How We Do It" Jamaal510 Feb 2013 #83
Most of My Dying Brides stuff Arcanetrance Feb 2013 #84
The Wreck of the Edmund Fitzgerald probably ranks up there somewhere Art_from_Ark Feb 2013 #86
A few more. bluedigger Feb 2013 #87
Turn The Page - Metallica distantearlywarning Feb 2013 #88
Can't You See? KG Feb 2013 #89
The Fields of Athenry lost-in-nj Feb 2013 #93
My generation (Y?): Socal31 Feb 2013 #94
The Last Time I Saw Richard Zorro Feb 2013 #95
Pretty much anything acoustic by Aaron Lewis. Socal31 Feb 2013 #97
"Learning the Game" as sung by Leo Kottke DFW Feb 2013 #98
Down To Seeds And Stems Again Blues PuffedMica Feb 2013 #100
couple of more, just for sadness Tuesday Afternoon Feb 2013 #101
This song always gets me. Still Blue in PDX Feb 2013 #107
Waltzing Matilda ornotna Feb 2013 #113
The sad final scene in the film On The Beach aint_no_life_nowhere Feb 2013 #114
Strange Fruit. whistler162 Feb 2013 #115
Mazzy Star Ahpook Feb 2013 #116
Hate Me sweetNsassy Feb 2013 #117
Most of Tom Waits' catalog. He once covered "Pancho and Lefty" Recursion Feb 2013 #118
A song from the 90s actually banned by the label when they still had control of artists... Socal31 Feb 2013 #119
I have to agree on 'Hurt'. polly7 Feb 2013 #120
Night Dig (Bring Me the Head of Alfredo Garcia) - Jerry Fielding MrScorpio Feb 2013 #121
Julie's Sixteenth Birthday by John Bult jmowreader Feb 2013 #122
Eric Clapton's "Tears in Heaven" mithnanthy Feb 2013 #123
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