top 100 saddest songs of all time

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94. "Lucille," Anthony Hamilton. This shit will KILL you.

Haibun (Begs2Differ), Friday, 3 December 2004 05:37 (nineteen years ago) link

93. "This Woman's Work" by Kate Bush -- I sincerely cannot hear Ms. Bush torturedly plead "OH, DARLIN' MAKE IT GO AWAY!" without welling up like a grandmother.

Alex in NYC (vassifer), Friday, 3 December 2004 05:38 (nineteen years ago) link

92. "Missing" by Everything But the Girl -- Sorry, I know I'm going to get pelted with rocks and garbage for this one, but seriously, this is one sincerely sad tune. C'mon,.....she's still taking trains to walk up and down this guy's block, and years have gone by since he's lived there? GET OVER IT, WOMAN!

Alex in NYC (vassifer), Friday, 3 December 2004 05:39 (nineteen years ago) link

91. "I'm So Lonesome I Could Cry," Hank Williams.

Haibun (Begs2Differ), Friday, 3 December 2004 05:40 (nineteen years ago) link

90. "Tha Crossroads," Bone Thugs N Harmony.

Haibun (Begs2Differ), Friday, 3 December 2004 05:42 (nineteen years ago) link

89. "Give Me the Reason" by Luther Vandross -- I ain't big for this type of stuff normally, but I so digs this bittersweet (accent on bitter) sentiment of the once-dumped lover not immediately accepting his presumptious dumper who has returned to his door. And sung so sweetly.

Alex in NYC (vassifer), Friday, 3 December 2004 05:43 (nineteen years ago) link

88. Neil Young -- Philadelphia

MindInRewind (Barry Bruner), Friday, 3 December 2004 05:43 (nineteen years ago) link

87 "wild is the wind" nina simone

equinox, Friday, 3 December 2004 05:43 (nineteen years ago) link

86. "Nothing Compares 2 U" by Sinead O'Connor -- Fuck Prince, she owns it.

Alex in NYC (vassifer), Friday, 3 December 2004 05:44 (nineteen years ago) link

86. Sinead O'Conner - "Nothing Compares 2 U" with apologies for this entry.

xpost. disregard it.

cws (cws), Friday, 3 December 2004 05:45 (nineteen years ago) link

85. "Twenty-Four Hours" by Joy Division -- Sad in block capital letters.

Alex in NYC (vassifer), Friday, 3 December 2004 05:46 (nineteen years ago) link

84. "climbing up the walls" radiohead

cb, Friday, 3 December 2004 05:47 (nineteen years ago) link

Lots of stuff here:
Top 100 - Tearjerking Techno.

... but I'll name one I forgot to put on that thread

83. Global Communication -- 12 18

MindInRewind (Barry Bruner), Friday, 3 December 2004 05:48 (nineteen years ago) link

83. "Stay" by Shakespeare's Sister -- I was never a fan, but when Ms.Detroit wails so emphatically towards the end of the song, her desperation is positively palpable.

Alex in NYC (vassifer), Friday, 3 December 2004 05:48 (nineteen years ago) link

83. The Beach Boys - "Caroline, No"

cws (cws), Friday, 3 December 2004 05:48 (nineteen years ago) link

80. "I'm Not Quite," David Bowie

jaymc (jaymc), Friday, 3 December 2004 05:49 (nineteen years ago) link

79. Leonard Cohen - "Hey, That's No Way to Say Goodbye"

cws (cws), Friday, 3 December 2004 05:51 (nineteen years ago) link

78. "Apologia" by Gavin Friday & the Man Seezer -- Total histrionic cabaret ala Brel & Piaf, but done so evocatively.....Gavin writhes around on the floor of some Parisian flophouse, lamenting a soiled love. BRILLIANCE

Alex in NYC (vassifer), Friday, 3 December 2004 05:51 (nineteen years ago) link

77. trembling blue stars - nobody but you

the surface noise (slight return) (electricsound), Friday, 3 December 2004 05:51 (nineteen years ago) link

76. The Smiths -- Please Please Please Let Me Get What I Want
75. ABBA -- Dancing Queen (OK, hands up -- who else thinks this is a very sad song?)

MindInRewind (Barry Bruner), Friday, 3 December 2004 05:51 (nineteen years ago) link

Them - "It's All Over Now, Baby Blue" -- man, but does this one always get me.

cws (cws), Friday, 3 December 2004 05:52 (nineteen years ago) link

74. Husker Du, "Hardly Getting Over It"

m.e.a. (m.e.a.), Friday, 3 December 2004 05:52 (nineteen years ago) link

74. "please push no more" -- gary numan
73. "atmosphere" -- joy division
72. "all that i've got is you" -- ghostface killah (w/ mary j blige)

Eisbär (llamasfur), Friday, 3 December 2004 05:53 (nineteen years ago) link

73. "Boot Camp" by Soundgarden -- Betcha didn't think they'd appear here, eh? Last song on their last album. Chris Cornell mournfully postulates about a better, brighter, happier place far, far away -- but one he'll never know, as he'll be stuck where he is for good.

Alex in NYC (vassifer), Friday, 3 December 2004 05:53 (nineteen years ago) link

68. "iron man" - black sabbath. i mean for fuck's sake, NOBODY WANTS HIM. and i don't care how much fucking revenge he gets, he's still got to be the most miserable superhero ever.

fact checking cuz (fcc), Friday, 3 December 2004 05:54 (nineteen years ago) link

67. "ghetto bastard (everything's gonna be alright)" -- naughty by nature

Eisbär (llamasfur), Friday, 3 December 2004 05:55 (nineteen years ago) link

67. "Can't Fight It" by Bob Mould -- Like a fist to the solar-plexus, this Mould breakup tune kills me everytime. So well done.

Alex in NYC (vassifer), Friday, 3 December 2004 05:55 (nineteen years ago) link

66. 'Gloomy Sunday' Billie Holiday

Kevin Gilchrist (Mr Fusion), Friday, 3 December 2004 05:55 (nineteen years ago) link

65. "when will i see you again?" -- the three degrees

Eisbär (llamasfur), Friday, 3 December 2004 05:56 (nineteen years ago) link

64. "He Likes Me" by the Violent Femmes -- Though quite jaunty and damn funny, the sentiment behind this tune (former boyfriend is livid with ex-girlfriend's new boyfriend expresses admiration for old boyfriend) is actually quite poignant. Translation: being dumped sucks.

Alex in NYC (vassifer), Friday, 3 December 2004 05:57 (nineteen years ago) link

hell yeah on the abba mention above - those swedes know melancholy

64. if drinking don't kill me, her memory will - george jones

Fritz Wollner (Fritz), Friday, 3 December 2004 05:57 (nineteen years ago) link

63. "lodi" -- creedence clearwater revival

Eisbär (llamasfur), Friday, 3 December 2004 05:58 (nineteen years ago) link

63. "Valentine's Day is Over" by Billy Bragg -- the fallout of an abusive relationship. Crushing line: "you'll find your things all stacked out on the landing." Ouch.

Alex in NYC (vassifer), Friday, 3 December 2004 05:58 (nineteen years ago) link

62. "Against All Odds" by Phil Collins -- Fuck you. It's the best song he ever pulled out of his ass. And it's a great, soppy, tear-jerker.

Alex in NYC (vassifer), Friday, 3 December 2004 05:59 (nineteen years ago) link

60. The Kinks - "Nothin' in This World Can Stop Me Worryin' 'bout That Girl"

cws (cws), Friday, 3 December 2004 05:59 (nineteen years ago) link

two weeks pass...
Oh well, the last backup happened only midway through this thread!

I'd attempt to repost the stuff I wrote before, but each and every thread is one of a kind and history can never be repeated. What is lost, is lost, and shall never be again, and trying to reassemble it bit by bit is fruitless.

So, let's create new history with songs we didn't cover last time:

59. Yo La Tengo -- Nowhere Near. A devastating portrait of loneliness. A perfect song in every way, from the way the drums slink into it midway through, to the sighing harmonies, to the sustained organ tones that slow the passing seconds to a crawl ...

MindInRewind (Barry Bruner), Tuesday, 21 December 2004 01:54 (nineteen years ago) link

I'd attempt to repost the stuff I wrote before, but each and every thread is one of a kind and history can never be repeated. What is lost, is lost, and shall never be again, and trying to reassemble it bit by bit is fruitless.

You otmfm, MIR.

Ken L (Ken L), Tuesday, 21 December 2004 04:04 (nineteen years ago) link

It was a great thread, though. And it still can be!

MindInRewind (Barry Bruner), Tuesday, 21 December 2004 04:07 (nineteen years ago) link

58. Candy Says - Velvet Undergound

Japanese Giraffe (Japanese Giraffe), Tuesday, 21 December 2004 07:20 (nineteen years ago) link

57. Waiting in Vain - Bob Marley

Forksclovetofu (Forksclovetofu), Tuesday, 21 December 2004 07:25 (nineteen years ago) link

56. "Jackson" - Lucinda Williams

Jazzbo (jmcgaw), Tuesday, 21 December 2004 12:36 (nineteen years ago) link

55. "Gone for Good" - Morphine
54. "Bird Stealing Bread" - Iron and Wine
53. "Winter" - Tori Amos

nickalicious (nickalicious), Tuesday, 21 December 2004 13:44 (nineteen years ago) link

"Gone For Good" is even sadder than intended, really, as it was supposed to just be a sortuv "okay then I'll leave you alone" breakup song and now, posthumously, takes on a much more heavy air.

nickalicious (nickalicious), Tuesday, 21 December 2004 13:58 (nineteen years ago) link

52. "I See A Darkness" -- Will Oldham (or the fantastic cover by Johnny Cash)

Surfer_Stone_Rosalita, Wednesday, 22 December 2004 03:54 (nineteen years ago) link

51. Red House Painters - "Katy Song"

Curt1s St3ph3ns, Wednesday, 22 December 2004 03:57 (nineteen years ago) link

I made a mix tape of sad songs once planning to give it to an ex and
ended up keeping it for myself and playing it for years. Some songs on it were:

51. Echo & The Bunnymen - Ocean Rain
50. R.E.M. - Perfect Circle
49. Rush - Losing It
48. The Cure - Sinking
47. David Sylvian & Ryuichi Sakamoto - Forbidden Colours
46. New Order - In A Lonely Place
45. Brian Eno - Spider & I
44. Japan - Night Porter
43. Robyn Hitchcock - I Used To Say I Love You

I still say the very saddest songs ALWAYS have piano in them. Even

42. Joy Division - The Eternal

and my vote for saddest song ever goes to:

41. This Mortal Coil - Holocaust (no I haven't heard the original but I can't see how it could possibly be any more sad - "your mother's dead", the rise and fall of strings and piano and one excellent performance by Howard Devoto)


Bimble..., Wednesday, 22 December 2004 06:20 (nineteen years ago) link

40. Glen Campbell - Wichita Lineman

derrick (derrick), Wednesday, 22 December 2004 06:36 (nineteen years ago) link

39. Frank Sinatra - Guess I'll Hang My Tears Out to Dry
Then somebody says, just forget about her
But I gave that treatment a try
Strangely enough, I got along without her
Then one day she passed me right by - oh well
I guess I?ll hang my tears out to dry

38. Beatles - For No One
And in her eyes you see nothing
No sign of love behind the tears
Cried for no one
A love that should have lasted years

Guuzbourg (Guuzbourg), Wednesday, 22 December 2004 14:40 (nineteen years ago) link

37. Roy Orbison - The Comedians (written by Elvis Costello, Orbisons version is better. Song's about a guy who quarrels with his girl, gets alone on a ferris wheel and when he's hanging there, he sees his girl flirting with the guy who operates the ferris wheel. In the end they leave him hanging there)

Guuzbourg (Guuzbourg), Wednesday, 22 December 2004 17:09 (nineteen years ago) link

Lyric:
I can hardly hear the music from the carousel
The wind picks up, the carriage starts sway
As one by one the lights go out
It’s closing time
I see you take his hand and walk away walk away

They say that you will always be the last to know
They say that all that glitters is not gold
It’s not just that you’re never coming back to me
It’s the bitter way that I was told

Guuzbourg (Guuzbourg), Wednesday, 22 December 2004 17:11 (nineteen years ago) link

Man, Taking Tiger Mountain brings the tears every time. Every time! And I'm mostly unemotional? Sort of?

an uptempo Pop/Hip Hop mentality (imago), Thursday, 6 April 2017 21:30 (seven years ago) link

five months pass...

No xpost

Week of Wonders (Ross), Monday, 25 September 2017 06:46 (six years ago) link

Carol - "So Low"

Sushi and the Banchan (Spectrist), Monday, 25 September 2017 07:08 (six years ago) link

"Flooding" by Kristin Hersh, the piano demo.

sick, fucking funny, and well tasty (katherine), Monday, 25 September 2017 17:20 (six years ago) link

"In This Hole" - Cat Power
"Holding" - Grouper
"For Martha" - the Smashing Pumpkins
"My New Freedom" - Elliott Smith
"Something in the Way" - Nirvana
"The End of the Rainbow" - Richard & Linda Thompson
"Sawdust & Diamonds" - Joanna Newsom
"God" - John Lennon
"This Night Has Opened My Eyes" - The Smiths
"Buzz Saw" - Xiu Xiu

flappy bird, Monday, 25 September 2017 18:05 (six years ago) link

People have some odd ideas on what constitutes a sad song.

The Doug Walters of Crime (Tom D.), Monday, 25 September 2017 18:07 (six years ago) link

A harder challenge would be coming up with some sadder than any of the songs on Mount Eerie's A Crow Looked at Me.

flappy bird, Monday, 25 September 2017 18:09 (six years ago) link

Yeah :-(

Le Bateau Ivre, Monday, 25 September 2017 18:12 (six years ago) link

I mean, Phil abandons/dismisses any attempt at making "art" on that record, because it's been rendered completely meaningless and useless to him. understandably. I couldn't get through 4 songs.

flappy bird, Monday, 25 September 2017 18:13 (six years ago) link

Sufjan Stevens - Carrie and Lowell is probably a contender for saddest album.

otm, I could listen to that one twice all the way through, and haven't revisited it since. songs are good, I just can't sink into that mood.

flappy bird, Monday, 25 September 2017 18:24 (six years ago) link

Little Green, Joni Mitchell – The wistful optimism is just heartbreaking

dinnerboat, Monday, 25 September 2017 18:26 (six years ago) link

oh man, I was gonna mention that one. "A Case of You" as well, even if it's more bittersweet. "Little Green" is similar to "This Night Has Opened My Eyes" - the complicated emotions that come with having an abortion / giving up a child for adoption.

flappy bird, Monday, 25 September 2017 18:28 (six years ago) link

River too -- subject matter is kind of run-of-the-mill as far as sad songs but the treatment is especially heartbreaking.

joni mitchell - other people's parties

Week of Wonders (Ross), Monday, 25 September 2017 18:57 (six years ago) link

Inconsolable - Jonatha Brooke

Bloody Snail, Monday, 25 September 2017 19:13 (six years ago) link

Zabelle Panosian, Groung (The Crane)

https://www.youtube.com/watch?v=GizgyxGSrFs

Mungolian Jerryset (bendy), Monday, 25 September 2017 19:49 (six years ago) link

one year passes...

The Train by Sinatra, off Watertown, a brutally sad album all told.

https://www.youtube.com/watch?v=dXP-417oiv0

Have the Rams stopped screaming yet, Lloris? (Chinaski), Sunday, 28 October 2018 12:21 (five years ago) link

Franz Schubert - 'Der Leiermann' (from Winterreise):

https://www.youtube.com/watch?v=sIIS-UgixGE

pomenitul, Sunday, 28 October 2018 12:33 (five years ago) link

six months pass...

The Band - It Makes No Difference

fancy the Dirkishness of carrying Doré a round (fionnland), Wednesday, 22 May 2019 21:53 (four years ago) link

the winner

i think ur a controp (voodoo chili), Wednesday, 22 May 2019 22:06 (four years ago) link

Bruce Springsteen, “Brilliant Disguise”

these are not all of the possible side effects (Karl Malone), Wednesday, 22 May 2019 22:15 (four years ago) link

Randy Newman - “Marie”

just thinking about that song, christ..

JoeStork, Wednesday, 22 May 2019 23:36 (four years ago) link

The Last Ride- Todd Rundgren

X-Prince Protégé (sonnyboy), Thursday, 23 May 2019 00:38 (four years ago) link

Kathleen Edwards - "Alicia Ross"

Josh in Chicago, Thursday, 23 May 2019 02:29 (four years ago) link

Josh Ritter - "The Curse"

Josh in Chicago, Thursday, 23 May 2019 02:29 (four years ago) link

Rickie Lee Jones - "Skeletons"

Herman Woke (cryptosicko), Thursday, 23 May 2019 02:30 (four years ago) link

also legit surprised not to see John Prine’s “Hello in There” in this thread.

JoeStork, Thursday, 23 May 2019 03:36 (four years ago) link

Sandy Denny - "All Our Days"

https://www.youtube.com/watch?v=MsxeL-59GbM

Brainless Addlepated Timid Muddleheaded Awful No-Account (Pheeel), Thursday, 23 May 2019 07:29 (four years ago) link

also legit surprised not to see John Prine’s “Hello in There” in this thread.

It's here.

kornrulez6969, Thursday, 23 May 2019 14:25 (four years ago) link

Peter Hammill, "This Side of the Looking-Glass"

the word dog doesn't bark (anagram), Thursday, 23 May 2019 14:39 (four years ago) link

Everybody's Been Burned by the Byrds
so sad it's haunted

Dr X O'Skeleton, Thursday, 23 May 2019 16:20 (four years ago) link

billy Bragg - tank park salute

brimstead, Thursday, 23 May 2019 16:42 (four years ago) link

Jason Isbell - "Elephant"

The Perfect Disaster - Down (Down)

mfktz (Camaraderie at Arms Length), Thursday, 23 May 2019 17:06 (four years ago) link

Dory Previn - "Beware of Young Girls" or "Mary C. Brown and the Hollywood Sign"

by the light of the burning Citroën, Thursday, 23 May 2019 17:27 (four years ago) link

anything by sibylle baier. colour green is the darkest LP i've ever heard, and that's coming from a regular elliott smith listener.

meaulnes, Thursday, 23 May 2019 17:36 (four years ago) link

A couple days ago, my daughter was singing "Maybe" from Annie, and I actually irl teared up. That song is inappropriately sad. It should be illegal except under tightly controlled circumstances.

mitt the hoopla (Ye Mad Puffin), Friday, 24 May 2019 13:36 (four years ago) link

41. This Mortal Coil - Holocaust (no I haven't heard the original but I can't see how it could possibly be any more sad - "your mother's dead", the rise and fall of strings and piano and one excellent performance by Howard Devoto)

― Bimble..., Wednesday, December 22, 2004 6:20 AM (fourteen years ago) Bookmark Flag Post Permalink

Fucking hell, I can't imagine knowing this song without being aware of the Big Star original. It's the pinnacle of devastation.

Brainless Addlepated Timid Muddleheaded Awful No-Account (Pheeel), Saturday, 25 May 2019 18:21 (four years ago) link

The Specials - I Can't Stand It

kitchen person, Saturday, 25 May 2019 19:36 (four years ago) link

most of the "sad songs" people talk about are to me encouraging and uplifting, which i guess says a lot about me. people with the saddest voices in the world like robert wyatt singing about how it'll be ok, no really, just make me think "yeah, they have a point, it will be ok". to me a really sad song is something like "you can make it if you try" by sly and the family stone.

Flood-Resistant Mirror-Drilling Machine (rushomancy), Saturday, 25 May 2019 19:42 (four years ago) link

I think I sort of know what you mean. Like, “what a wonderful world” fills me with deep deep despair

brimstead, Saturday, 25 May 2019 19:53 (four years ago) link

Sad songs say so much, even when they’re in another language (Turkish, in this case):

https://www.youtube.com/watch?v=zdngjh5cy5E

Sezen Aksu • Kavaklar

breastcrawl, Sunday, 26 May 2019 10:25 (four years ago) link

seasons in the sun

flappy bird, Tuesday, 28 May 2019 17:45 (four years ago) link


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