# Saddest song you know
**URL:** https://boards.straightdope.com/t/saddest-song-you-know/683461
**Category:** Cafe Society
**Created:** [March 11, 2014, 5:50pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461 "2014-03-11T17:50:15Z")
**Posts on this page:** 20
**Page:** 1
### Author:  [@Sir\_T-Cups](https://boards.straightdope.com/u/Sir_T-Cups)
#### Post date: [March 11, 2014, 5:50pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/1 "2014-03-11T17:50:15Z")
As I am listening to Pearl Jam’s Last Kiss, I am thinking that this might be the saddest song I know.
I am not THAT well versed in music, but a song about killing your girlfriend in a car accident is way more sad than “he broke up with me”.
What is everyone else’s nominations?
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### Author:  [@KneadToKnow](https://boards.straightdope.com/u/KneadToKnow)
#### Post date: [March 11, 2014, 5:51pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/2 "2014-03-11T17:51:12Z")
[“When Somebody Loved Me” from _Toy Story 2_](https://www.youtube.com/watch?v=px0j1EHF8Y0)
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### Author:  [@Infovore](https://boards.straightdope.com/u/Infovore)
#### Post date: [March 11, 2014, 5:52pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/3 "2014-03-11T17:52:45Z")
[30KFT](http://www.songlyrics.com/assemblage-23/30kft-lyrics/) by Assemblage 23.
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### Author:  [@jayjay](https://boards.straightdope.com/u/jayjay)
#### Post date: [March 11, 2014, 5:55pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/4 "2014-03-11T17:55:01Z")
Puff the Magic Dragon.
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### Author:  [@jimbuff314](https://boards.straightdope.com/u/jimbuff314)
#### Post date: [March 11, 2014, 5:59pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/5 "2014-03-11T17:59:03Z")
“At 17” Janis Ian
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### Author:  [@oft\_wears\_hats](https://boards.straightdope.com/u/oft_wears_hats)
#### Post date: [March 11, 2014, 6:04pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/6 "2014-03-11T18:04:35Z")
It’s been said before on this very forum, but I must nominate [And the Band Played Waltzing Matilda](http://en.wikipedia.org/wiki/And_the_Band_Played_Waltzing_Matilda).
From memory, so the lyrics may not be quite right:
> [@](#):
>
> And as our ship pulled into Circular Quay
> I looked at the place where me legs used to be
> And thanked Christ there was nobody waiting for me
> To grieve, and to mourn, and to pity.
>
> And the band played Waltzing Matilda
> As they carried us down the gangway.
> But nobody cheered, they just stood and stared
> And turned their faces away.
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### Author:  [@running\_coach](https://boards.straightdope.com/u/running_coach)
#### Post date: [March 11, 2014, 6:05pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/7 "2014-03-11T18:05:19Z")
_[Yesterday, When I Was Young](https://www.youtube.com/watch?v=NEY4LxORCeo)_-Roy Clark
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### Author:  [@woodstockbirdybird](https://boards.straightdope.com/u/woodstockbirdybird)
#### Post date: [March 11, 2014, 6:05pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/8 "2014-03-11T18:05:43Z")
The Pogues - [The Old Main Drag](https://www.youtube.com/watch?v=-xTsShIUx1Q)
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### Author:  [@Eonwe](https://boards.straightdope.com/u/Eonwe)
#### Post date: [March 11, 2014, 6:08pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/9 "2014-03-11T18:08:49Z")
[Keep Me In Your Heart](https://www.youtube.com/watch?v=Ee5zp8kQZj8) by Warren Zevon (who was diagnosed with terminal cancer before recording this album, and died two weeks after its release).
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### Author:  [@Chimera](https://boards.straightdope.com/u/Chimera)
#### Post date: [March 11, 2014, 6:09pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/10 "2014-03-11T18:09:30Z")
Alan Parsons - [The Very Last Time](http://www.youtube.com/watch?v=OkavKBVmkyg)
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### Author:  [@Dale\_Sams](https://boards.straightdope.com/u/Dale_Sams)
#### Post date: [March 11, 2014, 6:11pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/11 "2014-03-11T18:11:36Z")
He Stopped Loving Her Today.
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### Author:  [@Skald\_the\_Rhymer](https://boards.straightdope.com/u/Skald_the_Rhymer)
#### Post date: [March 11, 2014, 6:15pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/12 "2014-03-11T18:15:40Z")
The very first thing that comes to mind is “Lesson Number Eight,” from Stephen Sondheim’s musical _Sunday in the Park with George_. The speaker–the musicals main character, great-great-grandson of George Seurat–is mourning the death of his grandmother (and only relative) and his own growing alienation from the things that make life worth living. It’s beautiful and sad.
’
[Here it is.](http://www.youtube.com/watch?v=8io-sAU0JK4)
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### Author:  [@kenobi\_65](https://boards.straightdope.com/u/kenobi_65)
#### Post date: [March 11, 2014, 6:15pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/13 "2014-03-11T18:15:47Z")
Roy Orbison’s [In the Real World](http://www.youtube.com/watch?v=c-8Fxu8TEH0). It’s not “she broke up with me”, but “we’re deeply in love, but there’s no way that it’s going to work out.” A very sad theme, made sadder due to some personal relevance for me.
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### Author:  [@TheChileanBlob](https://boards.straightdope.com/u/TheChileanBlob)
#### Post date: [March 11, 2014, 6:19pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/14 "2014-03-11T18:19:22Z")
[Whiskey Lullaby](http://www.youtube.com/watch?v=IZbN_nmxAGk)
[Where’ve You Been](http://www.youtube.com/watch?v=nl5Uog-MDGo)
[What’s Your Mama’s Name](http://www.youtube.com/watch?v=fnJHc6CkggA)
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### Author:  [@Cat\_Whisperer](https://boards.straightdope.com/u/Cat_Whisperer)
#### Post date: [March 11, 2014, 6:20pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/15 "2014-03-11T18:20:51Z")
[Where’ve You Been?](https://www.youtube.com/watch?v=nl5Uog-MDGo) by Kathy Mattea. I dare you to listen to the whole song without tearing up.
ETA: Dammit, **Blob!**
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### Author:  [@bup](https://boards.straightdope.com/u/bup)
#### Post date: [March 11, 2014, 6:27pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/16 "2014-03-11T18:27:01Z")
[**Christmas Shoes.**](https://www.youtube.com/watch?v=dQw4w9WgXcQ)
Or maybe **Yesterday, When I Was Young** , as per **running coach** , above.
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### Author:  [@Amateur\_Barbarian](https://boards.straightdope.com/u/Amateur_Barbarian)
#### Post date: [March 11, 2014, 6:45pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/17 "2014-03-11T18:45:28Z")
“I’ll Be Home for Christmas” - for the utterly unforced pathos. Not a word of loss or loneliness or havin’ dun wrong, but the final lyric will always choke a sob out of me.
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### Author:  [@RealityChuck](https://boards.straightdope.com/u/RealityChuck)
#### Post date: [March 11, 2014, 6:55pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/18 "2014-03-11T18:55:02Z")
“[Father and Son](https://www.youtube.com/watch?v=Jek6iP6AuAQ)” by Cat Stevens. They’re both right – and they’re both wrong, and can’t understand how their perceptions differ.
“[Turn Around](https://www.youtube.com/watch?v=eCh13Rsd-WU)” by Malvina Reynolds is exquisitely sad.
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### Author:  [@Dale\_Sams](https://boards.straightdope.com/u/Dale_Sams)
#### Post date: [March 11, 2014, 6:59pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/19 "2014-03-11T18:59:44Z")
> [@RealityChuck](#):
>
> “[Father and Son](https://www.youtube.com/watch?v=Jek6iP6AuAQ)” by Cat Stevens. They’re both right – and they’re both wrong, and can’t understand how their perceptions differ.
>
> “[Turn Around](https://www.youtube.com/watch?v=eCh13Rsd-WU)” by Malvina Reynolds is exquisitely sad.
Cat Stevens and Ronan Keating do a brilliant version of “Father and Son”. I can’t link it cause I’m on the wife’s IPad, and am not proficient with it.
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### Author:  [@74westy](https://boards.straightdope.com/u/74westy)
#### Post date: [March 11, 2014, 7:05pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/20 "2014-03-11T19:05:26Z")
Woody Guthrie [1913 Massacre](http://www.youtube.com/watch?v=oz7oguguIZE).
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