# The saddest songs you ever heard **URL:** \ **Category:** Cafe Society\ **Created:** [May 8, 2011, 3:23am UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126 "2011-05-08T03:23:48Z")\ **Posts on this page:** 20\ **Page:** 2
**Author:** ![GuanoLad](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/guanolad/32/42_2.png) [@GuanoLad](https://boards.straightdope.com/u/GuanoLad)\ **Post date:** [May 8, 2011, 9:47am UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/21 "2011-05-08T09:47:27Z")
[Lonely Boy](http://www.youtube.com/watch?v=0kbgjmmr5vw), Andrew Gold ---
**Author:** ![orcenio](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/orcenio/32/1036_2.png) [@orcenio](https://boards.straightdope.com/u/orcenio)\ **Post date:** [May 8, 2011, 10:22am UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/22 "2011-05-08T10:22:39Z")
[Bill Withers - Grandma’s Hands](http://www.youtube.com/watch?v=qv5pagal-ls); a quite enjoyable song nonetheless. [Bill Withers - Ain’t No Sunshine](http://www.youtube.com/watch?v=tIdIqbv7SPo&feature=related); is just great. ---
**Author:** ![Horatio\_Hellpop](https://avatars.discourse-cdn.com/v4/letter/h/e5b9ba/32.png) [@Horatio\_Hellpop](https://boards.straightdope.com/u/Horatio_Hellpop)\ **Post date:** [May 8, 2011, 10:38am UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/23 "2011-05-08T10:38:09Z")
“Willing to Wait” by Sebadoh. ---
**Author:** ![orcenio](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/orcenio/32/1036_2.png) [@orcenio](https://boards.straightdope.com/u/orcenio)\ **Post date:** [May 8, 2011, 10:46am UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/24 "2011-05-08T10:46:16Z")
[Biggie Smalls - Suicidal Thoughts](http://www.youtube.com/watch?v=GygEAcFFMVs); yes, rappers can be deep (plus you get to hear a pre-famous P. Diddy). [Tupac - Papa’z Song](http://www.youtube.com/watch?v=NEJphAxfNjg); you can’t have a Biggie song without giving a shout to Tupac. [Tracy Chapman - Fast Car](http://www.youtube.com/watch?v=dl6yilkU1LI); glimpses of intergenerational poverty and quick fixes. ---
**Author:** ![don\_t\_ask](https://avatars.discourse-cdn.com/v4/letter/d/e68b1a/32.png) [@don\_t\_ask](https://boards.straightdope.com/u/don_t_ask)\ **Post date:** [May 8, 2011, 12:43pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/25 "2011-05-08T12:43:07Z")
A couple of Aussie ones: [Paul Kelly - How To Make Gravy](http://www.youtube.com/watch?v=Yb4YWJgfmQE) [I Was Only 19](http://www.youtube.com/watch?v=Urtiyp-G6jY) ---
**Author:** ![FoieGrasIsEvil](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/foiegrasisevil/32/16638_2.png) [@FoieGrasIsEvil](https://boards.straightdope.com/u/FoieGrasIsEvil)\ **Post date:** [May 8, 2011, 2:03pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/26 "2011-05-08T14:03:13Z")
Yeah, _Cat’s Cradle_ for me too. ---
**Author:** ![Mr\_Downtown](https://avatars.discourse-cdn.com/v4/letter/m/8e8cbc/32.png) [@Mr\_Downtown](https://boards.straightdope.com/u/Mr_Downtown)\ **Post date:** [May 8, 2011, 2:30pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/27 "2011-05-08T14:30:48Z")
_[I Never Will Marry.](http://www.youtube.com/watch?v=MKYfESMWfQE)_ I first heard Linda Ronstadt’s version, but I know there are others. Some personal significance, which I was beginning to realize at age 20. ---
**Author:** ![Cubsfan](https://avatars.discourse-cdn.com/v4/letter/c/f4b2a3/32.png) [@Cubsfan](https://boards.straightdope.com/u/Cubsfan)\ **Post date:** [May 8, 2011, 2:48pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/28 "2011-05-08T14:48:50Z")
> [@runner pat](#): > > Brad Paisley and Allison Krauss-_[Whiskey Lullaby](http://www.youtube.com/watch?v=IZbN_nmxAGk)_ This was one I came in to mention. I had never seen the video before today though and I’m glad I hadn’t. The song alone is so much better than with the cheesy video. Tears in Heaven by Clapton was very sad when he played it during Unplugged. I think it was the first time he ever played it live from what I heard. [http://www.youtube.com/watch?v=sSbqm7ZK\_9s](http://www.youtube.com/watch?v=sSbqm7ZK_9s) This live version of If You’re Readin This was very good by Tim McGraw. Very sad tune. [http://www.youtube.com/watch?v=dEjz-wAQLSA](http://www.youtube.com/watch?v=dEjz-wAQLSA) ---
**Author:** ![Glory](https://avatars.discourse-cdn.com/v4/letter/g/7cd45c/32.png) [@Glory](https://boards.straightdope.com/u/Glory)\ **Post date:** [May 8, 2011, 2:58pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/29 "2011-05-08T14:58:29Z")
Cat’s Cradle, for sure. Ye gods. This song always makes me cry - Death Cab for Cutie [Someday You Will be Loved](http://www.youtube.com/watch?v=18gDQU2gNkg). ---
**Author:** ![pythonzzz](https://avatars.discourse-cdn.com/v4/letter/p/9e8a1a/32.png) [@pythonzzz](https://boards.straightdope.com/u/pythonzzz)\ **Post date:** [May 8, 2011, 3:07pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/30 "2011-05-08T15:07:08Z")
Damn Aussies and Kiwis: “White Wine in the Sun” Tim Minchin [![](https://img.youtube.com/vi/fCNvZqpa-7Q/hqdefault.jpg "White Wine In The Sun by Tim Minchin") ](https://www.youtube.com/watch?v=fCNvZqpa-7Q) “Better Be Home Soon” Neil Finn’s live ARIA performance, in tribute to the late Paul Hester [![]( " - YouTube") ](https://www.youtube.com/watch?v=FD8pMIH1puw) ---
**Author:** ![vivalostwages](https://avatars.discourse-cdn.com/v4/letter/v/d07c76/32.png) [@vivalostwages](https://boards.straightdope.com/u/vivalostwages)\ **Post date:** [May 8, 2011, 3:11pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/31 "2011-05-08T15:11:04Z")
“Hurt,” no matter who sings it. “Don’t let the sun go down on me” by Elton John makes me sad, though I am not sure why. “Vibrate” by Rufus Wainwright—beautiful song about loneliness. Sad. ---
**Author:** ![NineToTheSky](https://avatars.discourse-cdn.com/v4/letter/n/b5a626/32.png) [@NineToTheSky](https://boards.straightdope.com/u/NineToTheSky)\ **Post date:** [May 8, 2011, 3:26pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/32 "2011-05-08T15:26:57Z")
Neil Young’s (with Buffalo Springfield) ode to a lost love is the saddest love song I’ve heard. \*I tried so hard to stand As I stumbled and fell to the ground. So hard to laugh as I fumbled And reached for the love I found, Knowin’ it was gone. If I never lived without you, Now you know I’d die. If I never said I loved you, Now you know I’d try, Babe, now you know I’d try. Babe, now you know I’d try, Babe. - ---
**Author:** ![beowulff](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/beowulff/32/542_2.png) [@beowulff](https://boards.straightdope.com/u/beowulff)\ **Post date:** [May 8, 2011, 3:34pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/33 "2011-05-08T15:34:41Z")
[Forever Autumn](http://www.youtube.com/watch?v=CO9Qx7Kp_I8) - Justin Hayward [If I Could Change Your Mind](http://www.youtube.com/watch?v=lrOWfW9_a0g) - The Alan Parsons Project. ---
**Author:** ![eclectic\_wench](https://avatars.discourse-cdn.com/v4/letter/e/ac91a4/32.png) [@eclectic\_wench](https://boards.straightdope.com/u/eclectic_wench)\ **Post date:** [May 8, 2011, 3:35pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/34 "2011-05-08T15:35:53Z")
Tom Waits. Oh gods, Tom Waits. ‘Cold Cold Ground’, ‘Georgia Lee’… I can barely even listen to ‘Green Grass’. Each of those has at least one line that just punches you straight in the solar plexus. Radiohead, ‘Exit Music’. ‘Hurt,’ the Johnny Cash version. ---
**Author:** ![GIGObuster](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/gigobuster/32/421_2.png) [@GIGObuster](https://boards.straightdope.com/u/GIGObuster)\ **Post date:** [May 8, 2011, 3:36pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/35 "2011-05-08T15:36:19Z")
This one was saddest because it came from a movie that was supposed to be fun. Toy Story 2: When Somebody Loved Me. Sarah McLachlan [![](https://i.ytimg.com/vi/px0j1EHF8Y0/hqdefault.jpg "Toy Story 2: When Somebody Loved Me.") ](https://www.youtube.com/watch?v=px0j1EHF8Y0) Made more sad when one realizes that the toys in the movies are the symbols or the avatars of the parents. ---
**Author:** ![Sateryn76](https://avatars.discourse-cdn.com/v4/letter/s/a88e4f/32.png) [@Sateryn76](https://boards.straightdope.com/u/Sateryn76)\ **Post date:** [May 8, 2011, 3:39pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/36 "2011-05-08T15:39:55Z")
[Billy Vera - At This Moment](http://www.youtube.com/watch?v=O2ur063fMhs) There’s something about it that’s different from most sad love songs. It’s unquestionably over, and the guy is just…sad. ---
**Author:** ![beowulff](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/beowulff/32/542_2.png) [@beowulff](https://boards.straightdope.com/u/beowulff)\ **Post date:** [May 8, 2011, 4:14pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/37 "2011-05-08T16:14:00Z")
Game over, man: [“I will wait for you”, - Connie Francis, from Futurama](http://www.youtube.com/watch?v=OjNw75bJyuM&feature=related) ---
**Author:** ![A\_Dodgy\_Dude](https://avatars.discourse-cdn.com/v4/letter/a/a87d85/32.png) [@A\_Dodgy\_Dude](https://boards.straightdope.com/u/A_Dodgy_Dude)\ **Post date:** [May 8, 2011, 4:28pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/38 "2011-05-08T16:28:35Z")
If this doesn’t make you blink back a tear or two there must be something wrong with your heart: [The Old Man - Celtic Thunder’s version](http://www.youtube.com/watch?v=7Cw1yorwijY) ---
**Author:** ![Tamerlane](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/tamerlane/32/7602_2.png) [@Tamerlane](https://boards.straightdope.com/u/Tamerlane)\ **Post date:** [May 8, 2011, 4:32pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/39 "2011-05-08T16:32:15Z")
Maybe less sad, than _harrowing_ - Lou Reed’s [The Kids](http://www.youtube.com/watch?v=Q3AEL9bhftw) from the album Berlin ( possibly the least happy record ever made ). ---
**Author:** ![TreacherousCretin](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/treacherouscretin/32/476_2.png) [@TreacherousCretin](https://boards.straightdope.com/u/TreacherousCretin)\ **Post date:** [May 8, 2011, 5:18pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/40 "2011-05-08T17:18:29Z")
Mine are all pop: Traces (Dennis Yost) Now You’re Gone (Boz Scaggs) Keep Me From Blowing Away (Linda Ronstadt) For No One (Beatles) Caroline, No (Brian Wilson) [Previous page](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126.md?page=1) [Next page](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126.md?page=3)