top 100 saddest songs of all time

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100. what becomes of the broken-hearted? - jimmy ruffin

Fritz Wollner (Fritz), Friday, 3 December 2004 05:10 (9 years ago) Permalink

99. up the junction - squeeze

Fritz Wollner (Fritz), Friday, 3 December 2004 05:11 (9 years ago) Permalink

98. go go round - gordon lightfoot

Fritz Wollner (Fritz), Friday, 3 December 2004 05:18 (9 years ago) Permalink

97. "Sunday Morning Coming Down" - Johnny Cash

so utterly hopeless. the stark, dirty bottom of the emotional barrel....

m0stly clean (m0stly clean), Friday, 3 December 2004 05:30 (9 years ago) Permalink

96. "end of the world" - skeeter davis. it's the end of the world as she knows it and she does NOT feel fine.

fact checking cuz (fcc), Friday, 3 December 2004 05:32 (9 years ago) Permalink

95. "silver wings" - merle haggard. sadness expressed so perfectly that he only had to write one short verse. a second verse might well have fucked it up.

fact checking cuz (fcc), Friday, 3 December 2004 05:36 (9 years ago) Permalink

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

Haibun (Begs2Differ), Friday, 3 December 2004 05:37 (9 years ago) Permalink

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 (9 years ago) Permalink

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 (9 years ago) Permalink

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

Haibun (Begs2Differ), Friday, 3 December 2004 05:40 (9 years ago) Permalink

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

Haibun (Begs2Differ), Friday, 3 December 2004 05:42 (9 years ago) Permalink

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 (9 years ago) Permalink

88. Neil Young -- Philadelphia

MindInRewind (Barry Bruner), Friday, 3 December 2004 05:43 (9 years ago) Permalink

87 "wild is the wind" nina simone

equinox, Friday, 3 December 2004 05:43 (9 years ago) Permalink

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

Alex in NYC (vassifer), Friday, 3 December 2004 05:44 (9 years ago) Permalink

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

xpost. disregard it.

cws (cws), Friday, 3 December 2004 05:45 (9 years ago) Permalink

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

Alex in NYC (vassifer), Friday, 3 December 2004 05:46 (9 years ago) Permalink

84. "climbing up the walls" radiohead

cb, Friday, 3 December 2004 05:47 (9 years ago) Permalink

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 (9 years ago) Permalink

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 (9 years ago) Permalink

83. The Beach Boys - "Caroline, No"

cws (cws), Friday, 3 December 2004 05:48 (9 years ago) Permalink

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

jaymc (jaymc), Friday, 3 December 2004 05:49 (9 years ago) Permalink

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

cws (cws), Friday, 3 December 2004 05:51 (9 years ago) Permalink

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 (9 years ago) Permalink

77. trembling blue stars - nobody but you

the surface noise (slight return) (electricsound), Friday, 3 December 2004 05:51 (9 years ago) Permalink

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 (9 years ago) Permalink

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

cws (cws), Friday, 3 December 2004 05:52 (9 years ago) Permalink

74. Husker Du, "Hardly Getting Over It"

m.e.a. (m.e.a.), Friday, 3 December 2004 05:52 (9 years ago) Permalink

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 (9 years ago) Permalink

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 (9 years ago) Permalink

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 (9 years ago) Permalink

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

Eisbär (llamasfur), Friday, 3 December 2004 05:55 (9 years ago) Permalink

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 (9 years ago) Permalink

66. 'Gloomy Sunday' Billie Holiday

Kevin Gilchrist (Mr Fusion), Friday, 3 December 2004 05:55 (9 years ago) Permalink

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

Eisbär (llamasfur), Friday, 3 December 2004 05:56 (9 years ago) Permalink

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 (9 years ago) Permalink

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 (9 years ago) Permalink

63. "lodi" -- creedence clearwater revival

Eisbär (llamasfur), Friday, 3 December 2004 05:58 (9 years ago) Permalink

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 (9 years ago) Permalink

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 (9 years ago) Permalink

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

cws (cws), Friday, 3 December 2004 05:59 (9 years ago) Permalink

2 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 (9 years ago) Permalink

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 (9 years ago) Permalink

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

MindInRewind (Barry Bruner), Tuesday, 21 December 2004 04:07 (9 years ago) Permalink

58. Candy Says - Velvet Undergound

Japanese Giraffe (Japanese Giraffe), Tuesday, 21 December 2004 07:20 (9 years ago) Permalink

57. Waiting in Vain - Bob Marley

Forksclovetofu (Forksclovetofu), Tuesday, 21 December 2004 07:25 (9 years ago) Permalink

56. "Jackson" - Lucinda Williams

Jazzbo (jmcgaw), Tuesday, 21 December 2004 12:36 (9 years ago) Permalink

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

nickalicious (nickalicious), Tuesday, 21 December 2004 13:44 (9 years ago) Permalink

"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 (9 years ago) Permalink

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

Surfer_Stone_Rosalita, Wednesday, 22 December 2004 03:54 (9 years ago) Permalink

"Ladies And Gentlemen We Are Floating In Space" by Spiritualized

andy dale (andy dale), Sunday, 28 May 2006 21:54 (8 years ago) Permalink

It probably wasn't intended to be a sad song, but the one that always brings a tear to my eye is John Lennon's Beautiful Boy-especially the part where he says " I can hardly wait to see you come of age" because as we all know, that is never going to happen.

Dwango, Friday, 2 June 2006 10:07 (8 years ago) Permalink

15. Billie Holiday - "You've Changed"

PB, Friday, 2 June 2006 10:59 (8 years ago) Permalink

14, Fleetwood Mac - Man Of The World

eyesteel (eyesteel), Friday, 2 June 2006 11:43 (8 years ago) Permalink

13. "my whole world ended (the moment you left me)" - david ruffin

12. "the bitterest pill" - the jam

11. "wise up" - aimee mann

Lawrence the Looter (Lawrence the Looter), Friday, 2 June 2006 12:11 (8 years ago) Permalink

10. Mark Eitzel - "Mission Rock Resort"
9. American Music Club - "I've Been A Mess (Since You've Been Gone)"
(not enough Eitzel/AMC on this thread)
8. Leonard Cohen - "Bird On A Wire"
7. Cat Power - "Water & Air"
6. Joy Divison - "Love Will Tear Us Apart"
(no one wants to pick the obvious one, but what the hell)
5. Nick Drake - "Which Will"

Edward III (edward iii), Friday, 2 June 2006 14:18 (8 years ago) Permalink

4. Jackson Browne--Late For The Sky

kornrulez6969 (TCBeing), Friday, 2 June 2006 14:23 (8 years ago) Permalink

3. Bruce Springsteen - "You're Missing"

PB, Friday, 2 June 2006 15:05 (8 years ago) Permalink

2. "No Regrets" - Tom Rush (covered by Walker Brothers, Emmylou Harris, etc.)

Joe (Joe), Friday, 2 June 2006 16:39 (8 years ago) Permalink

1. Tomorrow and Me, Michael Nesmith

Billy Pilgrim (Billy Pilgrim), Friday, 2 June 2006 17:18 (8 years ago) Permalink

On a related note...
Anyone have any opinions of this book?

I Hate Myself and Want to Die: The 52 Most Depressing Songs You've Ever Heard by Tom Reynolds
http://www.amazon.co.uk/exec/obidos/ASIN/1860746284/203-7908214-9069500

Leafed through it. The essay on "Prayers for Rain" by the Cure was hilarious.

Lord Custos Omicron (Lord Custos Omicron), Saturday, 3 June 2006 18:40 (8 years ago) Permalink

I know this is totally cheating but what the fuck...

0. hardly getting over it - husker du.
-1. borrowed tune - neil young

simon 803 (simon 803), Saturday, 3 June 2006 20:22 (8 years ago) Permalink

-2. Roberta Flack and Donny Hathaway - Back Together Again

Donny died during recording and Roberta's lyrics just go on and on without him... for about 10 minutes actually.... there is a lot of "I miss you" and futile language in this song.... it is really really sad in context.

JTS (JTS), Saturday, 3 June 2006 21:33 (8 years ago) Permalink

1 year passes...

I just put this up, if anyone's interested: The Walrus Magazine picks 30 of the saddest songs ever.

Includes contributions from sometime-ILX-person DaveM and, er, me. Feel free to leave some comments/abuse/recommendations.

Thanks, sorry, whorishness over.

Chuck_Tatum, Friday, 18 April 2008 20:18 (6 years ago) Permalink

mozart's requiem lol

davie, Friday, 18 April 2008 20:25 (6 years ago) Permalink

Great list. FWIW, another good sad (rock) song is Grant Hart's You Don't Have To Tell Me Now, which is unsettling in how direct it is.

Daniel, Esq., Friday, 18 April 2008 20:32 (6 years ago) Permalink

Some more that come to mind: Gregg Allman's All My Friends and his version of Jackson Browne's These Days, both of which are on the Laid Back disc; Chris Bell's You And Your Sister; The Clientele Dreams Of Leaving; Pernice Bros.' Number Two; Sun Kil Moon's Carry Me Ohio (not entirely sure about this one, but it feels right); Bruce Springsteen's One Step Up; Jimmy Cliff's Many Rivers To Cross; Richard Hawley's The Ocean (Again, I'm not totally sure about this one. In some ways, Hawley sounds hopeful and content; in others, he sounds like he's lost so much time and he's saying goodbye); and 2/3 of Billie Holiday's catalogue (and a good deal of Iron & Wine's early catalogue).

Daniel, Esq., Friday, 18 April 2008 20:54 (6 years ago) Permalink

Gnossienne No. 5, Modéré

Michael White, Friday, 18 April 2008 21:48 (6 years ago) Permalink

Biz Markie - Alone Again (Naturally)
[Grand Upright Music, Ltd. v. Warner Bros. Records, Inc.]

PappaWheelie V, Friday, 18 April 2008 22:00 (6 years ago) Permalink

Hello In There--John Prine

kornrulez6969, Friday, 18 April 2008 22:21 (6 years ago) Permalink

Did I see "Thousand Dollar Wedding" upthread? Not sure.

ellaguru, Friday, 18 April 2008 22:48 (6 years ago) Permalink

KATY SONG - RED HOUSE PAINTERS - shush

Fer Ark, Saturday, 19 April 2008 00:01 (6 years ago) Permalink

Can't believe this wasn't metioned: "I Know it's Over" - Smiths

Pillbox, Saturday, 19 April 2008 00:14 (6 years ago) Permalink

"It Never Entered My Mind" - Rodgers/Hart
"You're A Big Girl Now" - Bob Dylan
"So Long" - Rickie Lee Jones

iago g., Saturday, 19 April 2008 00:52 (6 years ago) Permalink

Michelle Shocked - "Stillborn"

Since I just finished the 33 1/3 book on Swordfishtrombone:

Tom Waits - "Soldier's Things"
"And this one is for bravery
And this one is for me
And everything's a dollar in this box"

Hideous Lump, Saturday, 19 April 2008 02:37 (6 years ago) Permalink

"How I Long to Feel that Summer" - Gorky's Zygotic Mynci

EMO, I know, but even when I was IN that summer this song felt sad and nostalgic.

Z S, Saturday, 19 April 2008 04:01 (6 years ago) Permalink

Roads - Portishead
All Things to All Men - Cinematic Orchestra and Roots Manuva

chap, Sunday, 20 April 2008 02:03 (6 years ago) Permalink

"Smalltown Boy", The Bronski Beat

daavid, Sunday, 20 April 2008 02:44 (6 years ago) Permalink

to broadly echo stuff from immediately upthread, so much of mark koz's or ricki lee's catalog brings on the sad

dell, Sunday, 20 April 2008 02:52 (6 years ago) Permalink

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.

yeah. why this one works, i don't pretend to understand. but, it does, against all odds, even.

dell, Sunday, 20 April 2008 02:57 (6 years ago) Permalink

"Teddy Bear" - Red Sovine
*sniffle*

gigabytepicnic, Sunday, 20 April 2008 03:04 (6 years ago) Permalink

http://www.youtube.com/watch?v=06MfMaxp8RU

gigabytepicnic, Sunday, 20 April 2008 03:05 (6 years ago) Permalink

Well you better believe I took my turn at riding Teddy Bear

Curt1s Stephens, Sunday, 20 April 2008 03:11 (6 years ago) Permalink

*stifles a laff*

gigabytepicnic, Sunday, 20 April 2008 03:24 (6 years ago) Permalink

Gnossienne No. 5, Modéré

qft

davie, Sunday, 20 April 2008 05:09 (6 years ago) Permalink

5 years pass...

i think we need to re-do this because nobody mentioned "halah" by mazzy star, which i can't listen to without crying (esp the line "you're leaving before my time").

Treeship, Wednesday, 19 June 2013 02:46 (1 year ago) Permalink

I have the same experience with Hope Sandoval's "Down the Steps", a portrait of someone who's in denial after the death of a friend. there's something very convincing in the way she avoids using the word "death" or any of its synonyms, slips confusedly between past and present tense, and mixes matter-of-fact observations about the body with incoherent musings about where the soul has gone. her quavering, uncertain delivery of the last line ("wake up, make us some tea") is just devastating.

☉.☉☂ (unregistered), Wednesday, 19 June 2013 04:30 (1 year ago) Permalink

that is a great one too. she is easily one of my favorite singers of all time. her voice is just so beautiful, clear and youthful yet darkened always by this palpable weight of despair, like she could just break down and start crying any second.

Treeship, Wednesday, 19 June 2013 04:39 (1 year ago) Permalink

Man of the World - Fleetwood Mac (Peter Green iteration)

Iago Galdston, Thursday, 20 June 2013 00:03 (1 year ago) Permalink

14, Fleetwood Mac - Man Of The World
― eyesteel (eyesteel), Friday, June 2, 2006 7:43 AM (7 years ago) Bookmark Flag Post Permalink

Oops! Sorry, eyesteel

Iago Galdston, Thursday, 20 June 2013 00:05 (1 year ago) Permalink

Any number of versions of Adagio for Strings -- hell, it even works "for horns":

bodacious ignoramus, Thursday, 20 June 2013 07:49 (1 year ago) Permalink

Stephin Merritt and two of his 69LS allies did a 'saddest songs' show in 2000:


I'm Forever Blowing Bubbles [Kenbrovin/Kellette]
Seasons in the Sun [Brell/McKuen]
I Live off You [X-Ray Spex]
He Hit Me (It Felt Like a Kiss) [Goffin/King]
My Man [Yvain/Willmetz/Charles/Pollock]
The Winner Takes It All [Abba]
Big Red Balloon [Lee Hazelwood]
Anywhere (Like the Moon) [Kid Montana]
The Silver Swan [based on a 16th century madrigal by Orlando Gibbons]Oh, Danny Boy [trad. Irish]
If You Go Away [Brell/McKuen]
Pretty in Pink [The Psychedelic Furs]
Maria, Maria [Merritt]
Some Small Hope [Astley/Sakamoto]
Don't Get Around Much Anymore [Duke Ellington]
In My Room [Pocktiss/Vance]
Measure of a Man [ld beghtol]
The Slave's Lament [Robert Burns]
Big Louise [Scott Walker]
An Hour Too Late - 1890s parlour ballad
As Soon As I Hang up the Phone [Conway Twitty]
The Butcher Boy [trad. Irish]
Send in the Clowns [Stephen Sondheim]
'Tis the Last Rose of Summer [trad. Irish; lyrics by Sir Thomas More] - Is That All There Is? [Leiber/Stoller; extra lyrics by Christina]

ballin' from Maine to Mexico (Dr Morbius), Thursday, 20 June 2013 18:45 (1 year ago) Permalink

which allies? was it LG Benghtol and Lemony Snicket? sounds awesome regardless.

Treeship, Thursday, 20 June 2013 18:56 (1 year ago) Permalink

Is broken hearted same as sad?

Cat Power - Still In Love
Palace - New Partner

nicky lo-fi, Thursday, 20 June 2013 19:31 (1 year ago) Permalink

it is. for cat power, my pick would be "maybe not".

Treeship, Thursday, 20 June 2013 19:33 (1 year ago) Permalink

Treeship, it was LD & Dudley Klute. (w/ SM, The Three Terrors)

ballin' from Maine to Mexico (Dr Morbius), Thursday, 20 June 2013 19:56 (1 year ago) Permalink

that is a great one too. she is easily one of my favorite singers of all time. her voice is just so beautiful, clear and youthful yet darkened always by this palpable weight of despair, like she could just break down and start crying any second.

― Treeship, Wednesday, June 19, 2013 12:39 AM (Yesterday)

hmm, I don't really get an "on the verge of a breakdown" feeling from her music, apart from "On the Steps" and a few of the quieter Mazzy Star songs ("Look on Down From the Bridge"?). if anything it sounds like she could fall asleep any second, and the constant, low-level moodiness is perfect for when you're feeling tired and depressed but aren't in the mood for anything properly weepy.

☉.☉☂ (unregistered), Thursday, 20 June 2013 20:02 (1 year ago) Permalink

when i imagine the breakdown, it is like she is on the verge of quietly walking out of the studio and driving calmly back to her apartment and lying in bed lightly but ambivalently crying.

Treeship, Thursday, 20 June 2013 20:18 (1 year ago) Permalink

but i agree, there is a numbness there, which is familiar to anyone who has experienced really significant depression for a prolonged period of time. she sounds like she is suffering to me, i guess. but i still enjoy listening to the music and find it very beautiful.

Treeship, Thursday, 20 June 2013 20:19 (1 year ago) Permalink

well she does have a habit of quietly walking offstage in the middle of concerts, so you may have a point there (I kid). I've listened to her solo stuff so often while falling asleep that it's hard for me to hear it as anything but chill-out music — it's like I've conditioned myself to tune out the content/lyrics/emotions in favor of the vibes, maaaan. the same thing happens when I listen to certain music regularly while exercising. using music for purely functional purposes has its drawbacks.

oddly I don't like most of Mazzy Star's stuff, especially when they're in retro-psych mode, and I don't like Opal's heavier material (on Happy Nightmare Baby). Rain Parade completely bores me. sorry, Dave Roback, but I don't think I like you.

☉.☉☂ (unregistered), Thursday, 20 June 2013 20:43 (1 year ago) Permalink


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