# 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:** 5
**Author:** ![Alessan](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/alessan/32/465_2.png) [@Alessan](https://boards.straightdope.com/u/Alessan)\ **Post date:** [May 9, 2011, 5:05am UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/81 "2011-05-09T05:05:47Z")
It’s Memorial Day in Israel today, and in terms of sadness, you really can’t beat the songs they play on the radio today. You have “Flower”, “Winter of '73”, “Elifelet”, “The Medic’s Ballad”, and “Walking to Caesarea”. However, the saddest and most evocative one, at least to me, is “[The Little Prince](http://www.youtube.com/watch?v=Yke2mnYbBNs)”: \*I met him in the middle of the desert A beautiful sunset for a sad heart I drew him a sheep and a tree on a page And he promised he’d come back The little prince from Company B Won’t see another sheep eating a flower And all his roses are now thorns And his little heart is as cold as ice\* (Lyrics by Yehonatan Geffen; translation mine). ---
**Author:** ![Taomist](https://avatars.discourse-cdn.com/v4/letter/t/53a042/32.png) [@Taomist](https://boards.straightdope.com/u/Taomist)\ **Post date:** [May 9, 2011, 5:08am UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/82 "2011-05-09T05:08:02Z")
> [@vivalostwages](#): > > “Don’t let the sun go down on me” by Elton John makes me sad, though I am not sure why. This makes me choke up when I try to sing it, and I’m not sure why, either; the lyrics are sad, but there’s just something in the way he sings it that is oh so heartbreaking… On that note, his “Sacrifice” as well, Sinaed O’Connor’s version really tears it. And the Wilsons’ cover of “Daniel”, also. Peter Gabriel’s “I Grieve” kills me; I heard it for the first time right before my roommate’s mom died, and I spent about an hour listening to it over and over that day. Probably the one that is the best \ for me is Loreena McKennit’s “Dante’s Prayer”. So. Fucking. Haunting. When I die, well…yep. That’s the one. (The sad one, anyhoo; the one more fitting to my personality is Gabriel’s “Solsbury Hill”) ---
**Author:** ![zoog](https://avatars.discourse-cdn.com/v4/letter/z/7ea924/32.png) [@zoog](https://boards.straightdope.com/u/zoog)\ **Post date:** [May 9, 2011, 5:31am UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/83 "2011-05-09T05:31:19Z")
This topic pops up now and then, and I always have to chime in with John Prine’s [Sam Stone](http://www.youtube.com/watch?v=tafy0RVXNOo). “There’s a hole in daddy’s arm where all the money goes. Jesus Christ died for nothin’, I suppose.” Wow. And then there’s Patty Griffin’s [Long Ride Home](http://www.youtube.com/watch?v=A8HQu_hn6xA&feature=related). “40 years go by with someone layin’ in your bed. 40 years of things you say you wish you never said. How hard would it have been to say some kinder words instead? I wonder as I stare up at the sky a turning red.” If that doesn’t get to you, I don’t know what will. ---
**Author:** ![Peanuthead](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/peanuthead/32/360_2.png) [@Peanuthead](https://boards.straightdope.com/u/Peanuthead)\ **Post date:** [May 9, 2011, 5:43am UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/84 "2011-05-09T05:43:26Z")
Ray Charles talking to his mama on [Going Down Slow](http://www.youtube.com/watch?v=pOc9uK0InCY). I swear he gets himself choked up on this one. ---
**Author:** ![Carmady](https://avatars.discourse-cdn.com/v4/letter/c/f04885/32.png) [@Carmady](https://boards.straightdope.com/u/Carmady)\ **Post date:** [May 9, 2011, 7:09am UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/85 "2011-05-09T07:09:05Z")
Lots of sad songs here, but the saddest I’ve ever heard is Holocaust by Big Star. ---
**Author:** ![PapSett](https://avatars.discourse-cdn.com/v4/letter/p/ecc23a/32.png) [@PapSett](https://boards.straightdope.com/u/PapSett)\ **Post date:** [May 9, 2011, 1:59pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/86 "2011-05-09T13:59:23Z")
Another that chokes me up everytime is ‘Shannon’ by Henry Gross… about a childhood Irish Setter that drowned. _‘Shannon is gone, I hear she drifted off to sea. She always loved to swim away. Maybe she’ll find an island, with a shady tree, Just like the one in our backyard.’_ ---
**Author:** ![An\_Gadai](https://avatars.discourse-cdn.com/v4/letter/a/d6d6ee/32.png) [@An\_Gadai](https://boards.straightdope.com/u/An_Gadai)\ **Post date:** [May 9, 2011, 2:05pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/87 "2011-05-09T14:05:10Z")
_Facing The Chair_ by Patrick Street is a song I find very, very sad. It’s sung from the perspective of Bartolomeo Vanzetti. ---
**Author:** ![cjepson](https://avatars.discourse-cdn.com/v4/letter/c/a9adbd/32.png) [@cjepson](https://boards.straightdope.com/u/cjepson)\ **Post date:** [May 9, 2011, 4:16pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/88 "2011-05-09T16:16:05Z")
[“Your Long Journey”](http://www.youtube.com/watch?v=o9TmJBBKYmU) by Robert Plant & Alison Krauss ["Carmelita"](http://www.youtube.com/watch?v=B9L8jLPE84g)by Warren Zevon [“Angel from Montgomery”](http://www.youtube.com/watch?v=vhe3vb0z7mY) by Bonnie Raitt [“Last Train from Poor Valley”](http://www.youtube.com/watch?v=XwWlwpfFN0g) by Norman Blake ["How Will I Ever Be Simple Again"](http://www.youtube.com/watch?v=owodGwwjv_o)by Richard Thompson ---
**Author:** ![lieu](https://avatars.discourse-cdn.com/v4/letter/l/c2a13f/32.png) [@lieu](https://boards.straightdope.com/u/lieu)\ **Post date:** [May 9, 2011, 4:24pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/89 "2011-05-09T16:24:48Z")
> [@PapSett](#): > > For personal reasons, ‘At 17’ by Janice Ian. > > It came out about that time in my life, and I swear to God it felt like she was singing about me. A horrible, gut-wrenching time in my life where I started to figure out there were no happy-ever-afters for girls like me. After all these years, the song still brings me to tears. > > Every, single time. Yep, her pain is palpable. That and Taps. ---
**Author:** ![DirkGntly](https://avatars.discourse-cdn.com/v4/letter/d/d9b06d/32.png) [@DirkGntly](https://boards.straightdope.com/u/DirkGntly)\ **Post date:** [May 9, 2011, 4:42pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/90 "2011-05-09T16:42:54Z")
“Holes in the Floor of Heaven” - Stave Wariner. I always cry, even though it’s a great sentiment. The first first two lines always get me started, though: _One day shy if eight-years-old, my grandma passed away I was a broken-hearted little boy, blowing out that birthday cake…_ Also, “Wild Irish Rose” and The Grand Tour" - George Jones (the Aaron Neville version of Grand Tour is pretty good, too, but doesn’t grab me in the gut like George Jones) ---
**Author:** ![margin](https://avatars.discourse-cdn.com/v4/letter/m/65b543/32.png) [@margin](https://boards.straightdope.com/u/margin)\ **Post date:** [May 9, 2011, 7:03pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/91 "2011-05-09T19:03:54Z")
Joe Strummer’s version of “The Minstrel Boy” at the end of “Black Hawk Down”, especially after knowing what Shughart and Gordon did—and that they knew what would happen. “And The Band Played Waltzing Matilda” reduces me to a puddle every time. ---
**Author:** ![FordTaurusSHO94](https://avatars.discourse-cdn.com/v4/letter/f/f07891/32.png) [@FordTaurusSHO94](https://boards.straightdope.com/u/FordTaurusSHO94)\ **Post date:** [May 9, 2011, 7:25pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/92 "2011-05-09T19:25:42Z")
I’m Gonna Get There Someday - Dierks Bentley ---
**Author:** ![Long\_Time\_First\_Time](https://avatars.discourse-cdn.com/v4/letter/l/ad7895/32.png) [@Long\_Time\_First\_Time](https://boards.straightdope.com/u/Long_Time_First_Time)\ **Post date:** [May 9, 2011, 8:11pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/93 "2011-05-09T20:11:15Z")
> [@kelly5078](#): > > “Long, Long Time” - Linda Ronstadt I’ll see that and raise you \*\*Love Has No P_ride_ [http://www.youtube.com/watch?v=NRis8zKQ\_u4](http://www.youtube.com/watch?v=NRis8zKQ_u4) Also Tori Amos’ Winter always puts a catch in my throat. ---
**Author:** ![Steophan](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/steophan/32/9595_2.png) [@Steophan](https://boards.straightdope.com/u/Steophan)\ **Post date:** [May 9, 2011, 8:18pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/94 "2011-05-09T20:18:41Z")
[One Last Goodbye](http://www.youtube.com/watch?v=qboXhmXFA9g) by Anathema, especially this recent acoustic version. A devastating song about the aftermath of a loved one’s suicide. > [@](#): > > And somehow I knew you could never never stay > And somehow I knew you would leave me > And in the early morning light > After a silent peaceful night > You took my heart away > oh I wish, I wish you could have stayed [Forgotten Hopes](http://www.youtube.com/watch?v=d3VVRQWf2HU), also by Anathema. > [@](#): > > Hey you rotting in your alcoholic shell > Banging on the walls of your intoxicated mind > Do you ever wonder why you were left alone > As your heart grew colder and finally turned to stone ---
**Author:** ![Hazle\_Weatherfield](https://avatars.discourse-cdn.com/v4/letter/h/e9bcb4/32.png) [@Hazle\_Weatherfield](https://boards.straightdope.com/u/Hazle_Weatherfield)\ **Post date:** [May 9, 2011, 8:19pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/95 "2011-05-09T20:19:53Z")
“Crow Chasing a Butterfly” by Shinedown. Add the video and it’s just stunningly heartbreaking. ---
**Author:** ![Infovore](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/infovore/32/420_2.png) [@Infovore](https://boards.straightdope.com/u/Infovore)\ **Post date:** [May 9, 2011, 8:23pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/96 "2011-05-09T20:23:39Z")
Another vote for Tori Amos’s “Winter,” Johnny Cash’s “Hurt,” and “When Somebody Loved Me.” Also, “[30KFT](http://www.youtube.com/watch?v=dRIce9AX2fc)” by Assemblage 23. I am physically incapable of listening to this song without losing it. ---
**Author:** ![ghostman](https://avatars.discourse-cdn.com/v4/letter/g/a3d4f5/32.png) [@ghostman](https://boards.straightdope.com/u/ghostman)\ **Post date:** [May 9, 2011, 8:47pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/97 "2011-05-09T20:47:32Z")
[Schindler’s List Main Title](http://www.youtube.com/watch?v=0yYikshdLcw) ---
**Author:** ![\_mostly\_Harmless](https://avatars.discourse-cdn.com/v4/letter/_/9d8465/32.png) [@\_mostly\_Harmless](https://boards.straightdope.com/u/_mostly_Harmless)\ **Post date:** [May 9, 2011, 8:54pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/98 "2011-05-09T20:54:41Z")
Both of the OP’s are on my list. Also **Brick** by Ben Fold’s Five. So melancholy. ---
**Author:** ![Doug\_K](https://avatars.discourse-cdn.com/v4/letter/d/b5ac83/32.png) [@Doug\_K](https://boards.straightdope.com/u/Doug_K)\ **Post date:** [May 9, 2011, 9:09pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/99 "2011-05-09T21:09:20Z")
What can be sadder than losing a loved one not because she died, not because she found someone else, but because she was sold? [Darling Nellie Gray](http://en.wikipedia.org/wiki/Nellie_Gray) ---
**Author:** ![cosmosdan](https://avatars.discourse-cdn.com/v4/letter/c/a6a055/32.png) [@cosmosdan](https://boards.straightdope.com/u/cosmosdan)\ **Post date:** [May 9, 2011, 9:43pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/100 "2011-05-09T21:43:13Z")
[If I had Only Known](http://www.youtube.com/watch?v=eeKv_qc_aOo), by Reba McIntyre She released after the tragic accident that killed many of her band members. [The Last Song](http://www.youtube.com/watch?v=wlD_XNMCjuo) by Elton John. [Previous page](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126.md?page=4) [Next page](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126.md?page=6)