# 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:** 9
**Author:** ![crucible](https://avatars.discourse-cdn.com/v4/letter/c/5f8ce5/32.png) [@crucible](https://boards.straightdope.com/u/crucible)\ **Post date:** [June 24, 2014, 1:20pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/162 "2014-06-24T13:20:36Z")
Starry, starry night Portraits hung in empty halls Frame-less heads on nameless walls With eyes that watch the world and can’t forget ---
**Author:** ![crucible](https://avatars.discourse-cdn.com/v4/letter/c/5f8ce5/32.png) [@crucible](https://boards.straightdope.com/u/crucible)\ **Post date:** [June 24, 2014, 1:23pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/163 "2014-06-24T13:23:49Z")
'll be seeing you In all the old familiar places That this heart of mine embraces All day and through ---
**Author:** ![Octarine](https://avatars.discourse-cdn.com/v4/letter/o/22d042/32.png) [@Octarine](https://boards.straightdope.com/u/Octarine)\ **Post date:** [June 24, 2014, 1:56pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/164 "2014-06-24T13:56:45Z")
> [@crucible](#): > > He kissed his boy as he lay sleeping > Then he turned around and headed home again > Slip slidin’ away > Slip slidin’ away > You know the nearer your destination > The more you’re slip slidin’ away I also love the second and last stanzas from that song: I know a woman; became a wife These are the very words she uses to describe her life She said a good day ain’t got no rain She said a bad day is when I lie in bed And think of things that might have been. If you haven’t heard it, for some reason I find the [demo](https://www.youtube.com/watch?v=ZlZ4sP6z6gI) to be even sadder than the final version. Another Paul Simon nomination, from [one of my favorite songs of his](http://www.lyricsfreak.com/p/paul+simon/america_20105970.html) (and just all time favorite songs, as well): Kathy, I’m lost, I said, though I knew she was sleeping I’m empty and aching and I don’t know why Counting the cars on the New Jersey turnpike They’ve all come to look for America, all come to look for America. I also love [“I Am a Rock”](http://www.azlyrics.com/lyrics/simongarfunkel/iamarock.html) - the last two lines sum it up: And a rock feels no pain; And an island never cries. My final Paul Simon one, [“Graceland”](http://www.azlyrics.com/lyrics/paulsimon/graceland.html) - the stanza that stands out to me is: She comes back to tell me she’s gone As if I didn’t know that As if I didn’t know my own bed. As if I’d never noticed The way she brushed her hair from her forehead. Huh. I started out intending to do one of his songs, and ended up with four. I guess he does sad really well. 😃 OK, last ones - so many Leonard Cohen songs, especially the very early ones, are achingly sad, but the two that stand out to me are [“Famous Blue Raincoat”](http://www.azlyrics.com/lyrics/leonardcohen/famousblueraincoat.html) and [“That’s No Way to Say Goodbye”](http://www.metrolyrics.com/hey-thats-no-way-to-say-goodbye-lyrics-leonard-cohen.html). The latter sounds like a “we’re-so-happy-together” love song, until you realize that she left him, and the former is just . . . depressing beyond all reasonable bounds, with some mystery thrown in. ---
**Author:** ![CheshireKat](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/cheshirekat/32/1207_2.png) [@CheshireKat](https://boards.straightdope.com/u/CheshireKat)\ **Post date:** [June 24, 2014, 1:59pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/165 "2014-06-24T13:59:46Z")
Most of mine have been mentioned, but I’ll add [Send In the Clowns](https://www.youtube.com/watch?v=8L6KGuTr9TI)sung by Judy Collins. Just hearing the oboe at the beginning immediately puts me in a sad place. Also [How To Save a Life](https://www.youtube.com/watch?v=qw0wRfHjF5M), by The Fray: Where did I go wrong? I lost a friend Somewhere along in the bitterness And I would have stayed up with you all night Had I known how to save a life When this song came out, my daughter’s close friend, such a sweet young soul, had just committed suicide. I couldn’t even listen to the entire song for about a year, and it still makes me cry. ---
**Author:** ![phungi](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/phungi/32/395_2.png) [@phungi](https://boards.straightdope.com/u/phungi)\ **Post date:** [June 24, 2014, 2:03pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/166 "2014-06-24T14:03:47Z")
> [@Labrador\_Deceiver](#): > > That’s a cover of a 1964 hit by J. Frank Wilson and the Cavaliers, for what it’s worth. correct… [more detail](http://en.wikipedia.org/wiki/Last_Kiss#Pearl_Jam_version), should anyone care ---
**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:** [June 24, 2014, 2:32pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/167 "2014-06-24T14:32:42Z")
> [@Octarine](#): > > (Paul Simon songs snipped) What about “Richard Cory”? _He freely gave to charity, he had the common touch, And they were grateful for his patronage and thanked him very much, So my mind was filled with wonder when the evening headlines read: “Richard Cory went home last night and put a bullet through his head.”_ Or “A Most Peculiar Man”: _To his silent world and his tiny room; And Mrs. Riordan says he has a brother somewhere Who should be notified soon. And all the people said, “What a shame that he’s dead, But wasn’t he a most peculiar man?”_ Paul Simon (with and without Garfunkel) made some pretty depressing music. Good, but depressing. ---
**Author:** ![crucible](https://avatars.discourse-cdn.com/v4/letter/c/5f8ce5/32.png) [@crucible](https://boards.straightdope.com/u/crucible)\ **Post date:** [June 24, 2014, 3:01pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/168 "2014-06-24T15:01:11Z")
And she said losing love Is like a window in your heart Everybody sees you’re blown apart Everybody sees the wind blow. I wanted to use that one, too. I slipped some of it into a poem I wrote about writing poems as an example of one that gives you an immediate emotional reaction. ---
**Author:** ![Marley23](https://avatars.discourse-cdn.com/v4/letter/m/45deac/32.png) [@Marley23](https://boards.straightdope.com/u/Marley23)\ **Post date:** [June 24, 2014, 3:06pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/169 "2014-06-24T15:06:48Z")
A reminder to everybody: please don’t quote more than five lines from any one song unless it’s in the public domain. Thank you. ---
**Author:** ![Annie-Xmas](https://avatars.discourse-cdn.com/v4/letter/a/ecc23a/32.png) [@Annie-Xmas](https://boards.straightdope.com/u/Annie-Xmas)\ **Post date:** [June 24, 2014, 3:16pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/170 "2014-06-24T15:16:50Z")
Tom Paxton’s Born on the Fourth of July: Now I wheel myself down to the crossroads of town, To see the young girls and their lovers. And my mind is afire, it’s alive with desire, Christ, I’d barely begun, now it’s over. In my wheelchair for life, my mechanical wife, I’m supposed to be cheerful and stoic. I’m your old tried-and-true, Yankee Doodle to you, Clean-cut, paralysed and heroic. I was born on the Fourth of July. No one more loyal than I. When my country said so, I was ready to go And I wish I’d been left there to die. ---
**Author:** ![bup](https://avatars.discourse-cdn.com/v4/letter/b/6bbea6/32.png) [@bup](https://boards.straightdope.com/u/bup)\ **Post date:** [June 24, 2014, 3:22pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/171 "2014-06-24T15:22:02Z")
> [@tim-n-va](#): > > Maybe not the saddest but when a bluegrass song starts with: “Two old friends shared a room in a home for the elderly”, you know that at least one of them isn’t going to make it to the end of the song. I think “when a bluegrass song starts” is enough to clue you in that somebody dies during the song. [QUOTE=someone else] [Christmas Shoes.](http://api.viglink.com/api/click?format=go&jsonp=vglnk_jsonp_14036232422988&key=ce270d38103a630c3181db372a25a052&libId=8dd3871d-3a5e-4be5-b877-a62c481eb20f&loc=http%3A%2F%2Fboards.straightdope.com%2Fsdmb%2Fshowthread.php%3Ft%3D718061&v=1&out=https%3A%2F%2Fwww.youtube.com%2Fwatch%3Fv%3DdQw4w9WgXcQ&ref=http%3A%2F%2Fboards.straightdope.com%2Fsdmb%2Fshowthread.php%3Fp%3D17489617&title=Saddest%20song%20you%20know%20-%20Straight%20Dope%20Message%20Board&txt=%3Cb%3EChristmas%20Shoes.%3C%2Fb%3E) [/quote] :rolleyes: ---
**Author:** ![Eutychus](https://avatars.discourse-cdn.com/v4/letter/e/a3d4f5/32.png) [@Eutychus](https://boards.straightdope.com/u/Eutychus)\ **Post date:** [June 24, 2014, 7:17pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/172 "2014-06-24T19:17:25Z")
The Waterboys: “[The Whole of the Moon](https://www.youtube.com/watch?v=pu7AR0-FRro)” Still breaks me up a little. ☹ ---
**Author:** ![gigi](https://avatars.discourse-cdn.com/v4/letter/g/a587f6/32.png) [@gigi](https://boards.straightdope.com/u/gigi)\ **Post date:** [June 24, 2014, 7:24pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/173 "2014-06-24T19:24:03Z")
> [@tim-n-va](#): > > Maybe not the saddest but when a bluegrass song starts with: “Two old friends shared a room in a home for the elderly”, you know that at least one of them isn’t going to make it to the end of the song. (Bed By The Window). Reminds me of “First Christmas” by Stan Rogers. Not the absolute saddest song I can think of, but very melancholy. ---
**Author:** ![UncleRojelio](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/unclerojelio/32/3160_2.png) [@UncleRojelio](https://boards.straightdope.com/u/UncleRojelio)\ **Post date:** [June 24, 2014, 7:42pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/174 "2014-06-24T19:42:39Z")
Fire and Rain, James Taylor Wreck of the Edmund Fitzgerald, Gordon Lightfoot El Paso, Marty Robbins ---
**Author:** ![Specklebang](https://avatars.discourse-cdn.com/v4/letter/s/b9bd4f/32.png) [@Specklebang](https://boards.straightdope.com/u/Specklebang)\ **Post date:** [June 24, 2014, 7:50pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/175 "2014-06-24T19:50:28Z")
The Gunners Dream - Pink Floyd Each Small Candle - Roger Waters Who By Fire - Leonard Cohen I apologize if these were already posted. ---
**Author:** ![pinkfreud](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/pinkfreud/32/17603_2.png) [@pinkfreud](https://boards.straightdope.com/u/pinkfreud)\ **Post date:** [June 24, 2014, 8:01pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/176 "2014-06-24T20:01:45Z")
I can’t listen to Ian Tyson’s “Barney” without breaking into tears. https://www.youtube.com/embed/1NCvnG8AMFo?feature=oembed&wmode=opaque&list=PLF8E5BD645D3F53DF ---
**Author:** ![running\_coach](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/running_coach/32/15836_2.png) [@running\_coach](https://boards.straightdope.com/u/running_coach)\ **Post date:** [June 24, 2014, 8:08pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/177 "2014-06-24T20:08:56Z")
Two from [Slim Dusty](http://en.wikipedia.org/wiki/Slim_Dusty) [The Biggest Disappointment](https://www.youtube.com/watch?v=CoaZQKqMt9M&feature=kp) Written by Joy McKean(Dusty’s wife) [Turn Him Out In The Long Yard](https://www.youtube.com/watch?v=ejwOsZWfgck&feature=kp) Written by Kelly Dixon ---
**Author:** ![leftfield6](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/leftfield6/32/18780_2.png) [@leftfield6](https://boards.straightdope.com/u/leftfield6)\ **Post date:** [June 24, 2014, 8:27pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/178 "2014-06-24T20:27:10Z")
> [@Ulfreida](#): > > [Kilkelly Ireland](https://www.youtube.com/watch?v=QRHQAtKbRTk). Came here to say this. And it’s a true story. Holy crap, can’t hear that without tearing up. ---
**Author:** ![gwendee](https://avatars.discourse-cdn.com/v4/letter/g/35a633/32.png) [@gwendee](https://boards.straightdope.com/u/gwendee)\ **Post date:** [June 24, 2014, 9:44pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/179 "2014-06-24T21:44:33Z")
> [@Eonwe](#): > > [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). That’s certainly a frontrunner for me. [Back When We Were Beautiful](https://www.youtube.com/watch?v=TUL9ZXk6IDQ) reduces to me a puddly mess. ---
**Author:** ![CheshireKat](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/cheshirekat/32/1207_2.png) [@CheshireKat](https://boards.straightdope.com/u/CheshireKat)\ **Post date:** [June 24, 2014, 10:30pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/180 "2014-06-24T22:30:38Z")
I am a huge Queen fan, and have always been moved to tears by _These Are the Days of Our Lives_. I cannot bear to watch the original video when Freddie Mercury was so thin, but I do like [this version](https://www.youtube.com/watch?v=CwOLXmnndCg)when Queen performed it after Freddie’s death. It’s both heartbreaking and heartwarming to me when the picture of a young Freddie appears and the audience cheers. Sorry the video quality isn’t up to par, but I can no longer access the official version of this performance. ---
**Author:** ![Sefton](https://avatars.discourse-cdn.com/v4/letter/s/5daacb/32.png) [@Sefton](https://boards.straightdope.com/u/Sefton)\ **Post date:** [June 24, 2014, 10:46pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/181 "2014-06-24T22:46:03Z")
[Look on Down from the Bridge](https://www.youtube.com/watch?v=LwVXkM_YxMg) by Mazzy Star [Previous page](https://boards.straightdope.com/t/saddest-song-you-know/683461.md?page=8) [Next page](https://boards.straightdope.com/t/saddest-song-you-know/683461.md?page=10)