# Saddest song you know **URL:** \ **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:** 2
**Author:** ![Meltdown](https://avatars.discourse-cdn.com/v4/letter/m/45deac/32.png) [@Meltdown](https://boards.straightdope.com/u/Meltdown)\ **Post date:** [March 11, 2014, 7:06pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/21 "2014-03-11T19:06:13Z")
I could probably come up with sadder songs, but this one came up on my iPod last week and it knocked the wind out of me. [The Man in the Bed](https://www.youtube.com/watch?v=-_Yi88Xzqsc) – Dave Alvin ---
**Author:** ![dougie\_monty](https://avatars.discourse-cdn.com/v4/letter/d/439d5e/32.png) [@dougie\_monty](https://boards.straightdope.com/u/dougie_monty)\ **Post date:** [March 11, 2014, 7:06pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/22 "2014-03-11T19:06:14Z")
“I Dreamed a Dream” from _Les Misérables._ “500 Miles from Home”–the guy really misses his family… ☹ “I Am a Rock” by Simon & Garfunkel; at the end: _And a rock feels no pain And an island never cries_ “Bird in a Gilded Cage.” (The composer went to a brothel to write it. It made the prostitutes cry. The composer commented, “If my song makes THEM cry I have a hit on my hands.”) Just about anything by Tammy Wynette ☹ ☹ ---
**Author:** ![QuickSilver](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/quicksilver/32/7832_2.png) [@QuickSilver](https://boards.straightdope.com/u/QuickSilver)\ **Post date:** [March 11, 2014, 7:09pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/23 "2014-03-11T19:09:42Z")
Always[haunting](http://www.youtube.com/watch?v=TJhPH16AJe8). ---
**Author:** ![Zeke\_N.Destroi](https://avatars.discourse-cdn.com/v4/letter/z/4af34b/32.png) [@Zeke\_N.Destroi](https://boards.straightdope.com/u/Zeke_N.Destroi)\ **Post date:** [March 11, 2014, 7:22pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/24 "2014-03-11T19:22:58Z")
[break out the tissues](http://www.youtube.com/watch?v=yZ2sa3tyvkI) ---
**Author:** ![StGermain](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/stgermain/32/2868_2.png) [@StGermain](https://boards.straightdope.com/u/StGermain)\ **Post date:** [March 11, 2014, 7:23pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/25 "2014-03-11T19:23:13Z")
_Fast Car_ by Tracy Chapman. A girl starts out enabling a drunk father, and escapes to a better life, which turns out to be enabling a drunk husband, raising their kids in poverty-level existence. No hope for a better future, and her kids will probably end up like their parents. StG ---
**Author:** ![Northern\_Piper](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/northern_piper/32/5304_2.png) [@Northern\_Piper](https://boards.straightdope.com/u/Northern_Piper)\ **Post date:** [March 11, 2014, 7:29pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/26 "2014-03-11T19:29:59Z")
Why, _[Baseball’s Sad Lexicon](http://en.wikipedia.org/wiki/Baseball's_Sad_Lexicon)_, of course: > [@](#): > > These are the saddest of possible words: > “Tinker to Evers to Chance.” Says so, right in the opening line. 😃 ---
**Author:** ![dougie\_monty](https://avatars.discourse-cdn.com/v4/letter/d/439d5e/32.png) [@dougie\_monty](https://boards.straightdope.com/u/dougie_monty)\ **Post date:** [March 11, 2014, 7:34pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/27 "2014-03-11T19:34:51Z")
In “Lineup for Yesterday,” Ogden Nash included these lines: E is for Evers, His jaw in advance; Never afraid To Tinker with Chance. ---
**Author:** ![Ulfreida](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/ulfreida/32/8014_2.png) [@Ulfreida](https://boards.straightdope.com/u/Ulfreida)\ **Post date:** [March 11, 2014, 7:38pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/28 "2014-03-11T19:38:01Z")
[Kilkelly Ireland](https://www.youtube.com/watch?v=QRHQAtKbRTk). ---
**Author:** ![Little\_Nemo](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/little_nemo/32/3120_2.png) [@Little\_Nemo](https://boards.straightdope.com/u/Little_Nemo)\ **Post date:** [March 11, 2014, 7:45pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/29 "2014-03-11T19:45:22Z")
[_Alone Again_](http://www.youtube.com/watch?v=D_P-v1BVQn8&feature=kp) by Gilbert O’Sullivan. The peppy music conceals how bleak the lyrics are. But if you listen the singer is telling about how terrible his life is and he’s too depressed to even commit suicide. ---
**Author:** ![DCnDC](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/dcndc/32/2842_2.png) [@DCnDC](https://boards.straightdope.com/u/DCnDC)\ **Post date:** [March 11, 2014, 7:55pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/30 "2014-03-11T19:55:15Z")
[Spanish Doll](http://www.youtube.com/watch?v=4E8Y62k0KYs&feature=kp) by Poe ---
**Author:** ![Helena330](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/helena330/32/531_2.png) [@Helena330](https://boards.straightdope.com/u/Helena330)\ **Post date:** [March 11, 2014, 8:00pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/31 "2014-03-11T20:00:24Z")
Mike & The Mechanics _The Living Years._ It came out right when my father died, and still breaks me up pretty badly. Can’t even see through the tears while I type. http://www.lyricsfreak.com/m/mike+the+mechanics/the+living+years\_20093565.html ---
**Author:** ![Octarine](https://avatars.discourse-cdn.com/v4/letter/o/22d042/32.png) [@Octarine](https://boards.straightdope.com/u/Octarine)\ **Post date:** [March 11, 2014, 8:03pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/32 "2014-03-11T20:03:10Z")
> [@Ulfreida](#): > > [Kilkelly Ireland](https://www.youtube.com/watch?v=QRHQAtKbRTk). I was about to post that! It’s one of the saddest songs I know, along with [The Green Fields of France](http://www.youtube.com/watch?v=ntt3wy-L8Ok). ---
**Author:** ![Labrador\_Deceiver](https://avatars.discourse-cdn.com/v4/letter/l/7c8e57/32.png) [@Labrador\_Deceiver](https://boards.straightdope.com/u/Labrador_Deceiver)\ **Post date:** [March 11, 2014, 8:09pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/33 "2014-03-11T20:09:23Z")
> [@Sir\_T-Cups](#): > > As I am listening to Pearl Jam’s Last Kiss, I am thinking that this might be the saddest song I know. That’s a cover of a 1964 hit by J. Frank Wilson and the Cavaliers, for what it’s worth. ---
**Author:** ![dataguy](https://avatars.discourse-cdn.com/v4/letter/d/eada6e/32.png) [@dataguy](https://boards.straightdope.com/u/dataguy)\ **Post date:** [March 11, 2014, 8:11pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/34 "2014-03-11T20:11:10Z")
Michael McDonald, [I Can Let Go Now](https://www.youtube.com/watch?v=tRsu7h7fzms). Heartbreak, plain and simple. Everytime I play this I have to immediately play something upbeat to clear the sadness from the room. ---
**Author:** ![Blaster\_Master](https://avatars.discourse-cdn.com/v4/letter/b/cab0a1/32.png) [@Blaster\_Master](https://boards.straightdope.com/u/Blaster_Master)\ **Post date:** [March 11, 2014, 8:12pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/35 "2014-03-11T20:12:36Z")
“One Last Goodbye” by Anathema I’m at work, so I can’t provide a link, but I don’t think I’ve ever heard a song that more perfectly captures grief. Three of the members are brothers, as as I understand, the song is their tribute to losing her to cancer. What makes it especially powerful is just how simple it is, the crescendo, and the sort of lyrics that very much mimic the words that go through my head when I’ve been in that kind of grief. It’s even more powerful as perhaps the centerpiece of a concept album that explores these concepts, and the song that follows. Regardless, Anathema is one of those bands I cannot highly recommend enough for anyone who even remotely likes prog rock; hell, even people I know who generally detest the genre have loved them. Go listen to it. ---
**Author:** ![Bellhorn](https://avatars.discourse-cdn.com/v4/letter/b/898d66/32.png) [@Bellhorn](https://boards.straightdope.com/u/Bellhorn)\ **Post date:** [March 11, 2014, 8:50pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/36 "2014-03-11T20:50:37Z")
[I Can’t Make You Love Me](http://www.youtube.com/watch?v=jNAsUTGGzoc) by Bonnie Raitt. Great song, but what a downer. “You can’t make your heart feel something it won’t” Whenever I hear this song, I want to contact Bonnie and tell her she’s not homely at all. (white lie) ---
**Author:** ![Hermione](https://avatars.discourse-cdn.com/v4/letter/h/cdc98d/32.png) [@Hermione](https://boards.straightdope.com/u/Hermione)\ **Post date:** [March 11, 2014, 9:09pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/37 "2014-03-11T21:09:25Z")
> [@Skald\_the\_Rhymer](#): > > 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) That is rather melancholy, but at least it’s alleviated by the songs that come after it-- “Move On” and the “Sunday” reprise. (The one line that always chokes me up is the last line of “Sunday”…“on an ordinary Sunday.” Because it WAS just an ordinary Sunday…and this artist made it extraordinary. That’s the wonder of art.) ---
**Author:** ![Biggirl](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/biggirl/32/3294_2.png) [@Biggirl](https://boards.straightdope.com/u/Biggirl)\ **Post date:** [March 11, 2014, 10:19pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/38 "2014-03-11T22:19:24Z")
Came in to mention Keep Me In Your Heart and was beat to it. I can’t even listen to it, it make me choke up. ---
**Author:** ![The\_Second\_Stone](https://avatars.discourse-cdn.com/v4/letter/t/bbe5ce/32.png) [@The\_Second\_Stone](https://boards.straightdope.com/u/The_Second_Stone)\ **Post date:** [March 11, 2014, 10:53pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/39 "2014-03-11T22:53:57Z")
Wharf Rat by The Grateful Dead. ---
**Author:** ![UnPossible1](https://avatars.discourse-cdn.com/v4/letter/u/dc4da7/32.png) [@UnPossible1](https://boards.straightdope.com/u/UnPossible1)\ **Post date:** [March 11, 2014, 10:55pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/40 "2014-03-11T22:55:18Z")
I’m Still Here by Tom Waits off his Alice album [![](https://img.youtube.com/vi/iLB0VEUerBY/maxresdefault.jpg "Tom Waits - I'm Still Here") ](https://www.youtube.com/watch?v=iLB0VEUerBY) [Previous page](https://boards.straightdope.com/t/saddest-song-you-know/683461.md?page=1) [Next page](https://boards.straightdope.com/t/saddest-song-you-know/683461.md?page=3)