# 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:** 8
**Author:** ![NineToTheSky](https://avatars.discourse-cdn.com/v4/letter/n/b5a626/32.png) [@NineToTheSky](https://boards.straightdope.com/u/NineToTheSky)\ **Post date:** [May 11, 2011, 3:24pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/141 "2011-05-11T15:24:12Z")
Don Henley’s ‘[A Month Of Sundays](http://www.youtube.com/watch?v=T4Ko3SMSAgY)’ (performed at Farm Aid 1985) about an old farmer looking back on his life, bemoaning how hard life is nowadays for ‘the independent man’. Very sad and very beautiful. **beagledave** mentioning Springsteen reminded me of, for me, his most beautiful sad song: [Racing In The Street](http://www.youtube.com/watch?v=vtQqQxD021Y). ---
**Author:** ![casdave](https://avatars.discourse-cdn.com/v4/letter/c/c6cbf5/32.png) [@casdave](https://boards.straightdope.com/u/casdave)\ **Post date:** [May 11, 2011, 4:01pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/142 "2011-05-11T16:01:57Z")
I am not keen of sad country songs, I’ve been over-cliched with them.You have to have a heart as hard as stone not to laugh out loud at most of them. So I suppose I’d better put up. Moira Kerr Mclain of Glencoe [![](https://img.youtube.com/vi/bjomiY0VOgk/hqdefault.jpg "Moira Kerr - MacIain of Glencoe") ](https://www.youtube.com/watch?v=bjomiY0VOgk) I’m surprised that Angel by Sarah Mclachlan has not had a mention [![]( " - YouTube") ](https://www.youtube.com/watch?v=Hx4RsCfL_fA) Sandy Denny - Who knows where the time goes [![](https://i.ytimg.com/vi/5oBMDcLf6WA/hqdefault.jpg "sandy denny - who knows where the time goes") ](https://www.youtube.com/watch?v=5oBMDcLf6WA) [![](https://i.ytimg.com/vi/n2xODjbfYw8/hqdefault.jpg "Who knows where the time goes - Fairport Convention") ](https://www.youtube.com/watch?v=n2xODjbfYw8) Everthing but the girl - Missing - Acoustic version (very haunting song) [![]( " - YouTube") ](https://www.youtube.com/watch?v=6E1P9-KfJ6I) [![](https://img.youtube.com/vi/dcG1Eqfp3M4/maxresdefault.jpg "Everything but the girl - Missing") ](https://www.youtube.com/watch?v=dcG1Eqfp3M4) Massive Attack - Protection [![](https://img.youtube.com/vi/Epgo8ixX6Wo/maxresdefault.jpg "Massive Attack - Protection") ](https://www.youtube.com/watch?v=Epgo8ixX6Wo) Bread - Diary [![](https://i.ytimg.com/vi/24IfD-0VUu4/hqdefault.jpg?sqp=-oaymwEmCOADEOgC8quKqQMa8AEB-AG-AoAC8AGKAgwIABABGGUgVyhGMA8=&rs=AOn4CLC1ntaThCmGm0CWmPSc0f6uLTL0vA "diary bread") ](https://www.youtube.com/watch?v=24IfD-0VUu4) Mary Chapin Carpenter - Only a dream [![](https://i.ytimg.com/vi/dDSdC4iQ-Xc/hqdefault.jpg "mary chapin carpenter- only a dream") ](https://www.youtube.com/watch?v=dDSdC4iQ-Xc) [![]( " - YouTube") ](https://www.youtube.com/watch?v=rhlF56wzgIU) The Walker brothers - No regrets - cheesy vid but good sound quality [![]( " - YouTube") ](https://www.youtube.com/watch?v=SY98RRYllxs) If you have ever been to the place where this song is, this will hit home Eleanor McEvoy - The heart of a woman [![](https://img.youtube.com/vi/tjQP9931NhU/hqdefault.jpg "Eleanor McEvoy - only a woman's heart") ](https://www.youtube.com/watch?v=tjQP9931NhU) Don Maclean - Castles in the air [![](https://i.ytimg.com/vi/TTqi7iEZEWA/hqdefault.jpg "Castle in the air - Don McLean Original") ](https://www.youtube.com/watch?v=TTqi7iEZEWA) Don Maclean - Empty Chairs [![](https://i.ytimg.com/vi/AwzHlyVRc9o/hqdefault.jpg "Empty Chair with Lyrics - Don McLean") ](https://www.youtube.com/watch?v=AwzHlyVRc9o) Gordon Lightfoot - The way I feel [![](https://i.ytimg.com/vi/AMOgpau2nkE/hqdefault.jpg "GORDON LIGHTFOOT ~ The Way I Feel ~") ](https://www.youtube.com/watch?v=AMOgpau2nkE) George Michael - You have been loved [![]( " - YouTube") ](https://www.youtube.com/watch?v=sCsbxLnVEaA) Beth Orton - She Cries your name [![](https://img.youtube.com/vi/rFZc4ax4tJs/maxresdefault.jpg "Beth Orton - She Cries Your Name (Video)") ](https://www.youtube.com/watch?v=rFZc4ax4tJs) ---
**Author:** ![GargoyleWB](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/gargoylewb/32/199_2.png) [@GargoyleWB](https://boards.straightdope.com/u/GargoyleWB)\ **Post date:** [May 11, 2011, 6:19pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/143 "2011-05-11T18:19:50Z")
I refuse to listen to **John Prine’s** “Hello in There” anymore. An avalanche of youthful guilt and the fear of growing old. **Neil Young’s** “Needle and the Damage Done” gets me, as do many other songs about wasted potential. **Pink Floyd’s** “Shine on you Crazy Diamond” is another. ---
**Author:** ![QuarkChild](https://avatars.discourse-cdn.com/v4/letter/q/c5a1d2/32.png) [@QuarkChild](https://boards.straightdope.com/u/QuarkChild)\ **Post date:** [May 11, 2011, 7:12pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/144 "2011-05-11T19:12:59Z")
The Wreck of the Edmund Fitzgerald I used to live in Ohio, and when they’d get to the line “just 20 miles from Cleveland” it would give me shivers. ---
**Author:** ![QuarkChild](https://avatars.discourse-cdn.com/v4/letter/q/c5a1d2/32.png) [@QuarkChild](https://boards.straightdope.com/u/QuarkChild)\ **Post date:** [May 11, 2011, 7:33pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/145 "2011-05-11T19:33:28Z")
Apparently I have a really bad memory…here are the actual lyrics that I conflated: “When they left fully loaded for Cleveland … The searchers all say they’d have made Whitefish Bay If they’d put fifteen more miles behind her.” ---
**Author:** ![cosmosdan](https://avatars.discourse-cdn.com/v4/letter/c/a6a055/32.png) [@cosmosdan](https://boards.straightdope.com/u/cosmosdan)\ **Post date:** [May 11, 2011, 9:12pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/146 "2011-05-11T21:12:10Z")
[Is it Over Yet?](http://www.youtube.com/watch?v=jL1Ma2yVA10) By Wynonna. Although it’s specifically about a relationship songs this poignant remind me of the sense of loss that comes with drastic change and loss that can come in many forms. ---
**Author:** ![Dr.Rieux](https://avatars.discourse-cdn.com/v4/letter/d/aeb1de/32.png) [@Dr.Rieux](https://boards.straightdope.com/u/Dr.Rieux)\ **Post date:** [May 11, 2011, 9:20pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/147 "2011-05-11T21:20:58Z")
Don Maclean’s “Vincent” gets me every time. Kristofferson’s “Jody and the Kid” ---
**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 11, 2011, 9:21pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/148 "2011-05-11T21:21:10Z")
[“Glenn Tipton”](http://www.youtube.com/watch?v=YjA3EbKsl4E) by **Sun Kil Moon** is another one that has made me weep on occasion. Also [On Raglan Road](http://www.youtube.com/watch?v=EuafmLvoJow)- Luke Kelly [There Were Roses](http://www.youtube.com/watch?v=bGMPUYfVw20) - Cara Dillion ---
**Author:** ![The\_Raven\_1](https://avatars.discourse-cdn.com/v4/letter/t/7993a0/32.png) [@The\_Raven\_1](https://boards.straightdope.com/u/The_Raven_1)\ **Post date:** [May 12, 2011, 6:41pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/149 "2011-05-12T18:41:30Z")
[“Without Your Love” - Roger McGuinn, from the _Back From Rio_ CD](http://www.youtube.com/watch?v=oN5df_UFfLE) The deep quaver in McGuinn’s voice just guts me. Add David Crosby and Chris Hillman doing sad, sad harmonies, and it’s a real tearjerker. I can’t even sing the song, because I get choked up about halfway in. Something about that plaintive tone just does me in. I’ve always characterized this song as"music to write your suicide note by". ---
**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 12, 2011, 8:14pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/150 "2011-05-12T20:14:20Z")
[The Green Fields Of Canada](http://www.youtube.com/watch?v=TcFeTMeP-kw) - Mary Dillon. ---
**Author:** ![Aeris](https://avatars.discourse-cdn.com/v4/letter/a/a183cd/32.png) [@Aeris](https://boards.straightdope.com/u/Aeris)\ **Post date:** [May 13, 2011, 1:58pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/151 "2011-05-13T13:58:11Z")
> [@TreacherousCretin](#): > > More sad instrumental music: > > - “Ashokan Farewell” (Fiddle Fever): I suspect it’s been made sadder by its association with “Letter To Sarah” in Ken Burns’ Civil War program. > > . I feel like this song could go either way though. If you watch it in the Ken Burns Civil War doc then yeah it’s sad but if you listen to it on it’s own, it’s not so sad. Maybe I’m just saying this in order to justify me using it for my wedding coming up. I will be walking down the aisle to this song. Anywho…These are my puddle inducing songs… I came on here to vote for **Into the West** by Annie Lennox that plays during the credits for Return of the King. “Hope fades into the world of night. Through shadows falling out of memories and time. Don’t say we have come to journey’s end. White shores are calling, you and I will meet again.” Ugh. Another vote for **When Somebody Loved Me** and **If You’re Reading This**. The first time I heard the latter I was in the car and had to pull over because I couldn’t see the road through my tears. **Stay With Me** from Into the Woods. "Don’t you know what’s out there in the world? Someone has to shield you from the world. Stay with me. Princes wait there in the world, it’s true. Princes, yes, but wolves and humans, too. Stay at home. I am home. Who out there could love you more than I? What out there that I cannot supply? Stay with me. Stay with me, The world is dark and wild. Stay a child while you can be a child. With me." ---
**Author:** ![robardin](https://avatars.discourse-cdn.com/v4/letter/r/43a26b/32.png) [@robardin](https://boards.straightdope.com/u/robardin)\ **Post date:** [May 13, 2011, 4:47pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/152 "2011-05-13T16:47:13Z")
Both already mentioned, “Cat’s Cradle” is the first thing that comes to my mind. “Tears In Heaven” too, when I remember the real life circumstances of Clapton writing the song. > [@Sateryn76](#): > > Billy Vera - At This Moment > > There’s something about it that’s different from most sad love songs. It’s unquestionably over, and the guy is just…sad. I remember this song becoming a surprise hit after it was featured on that episode of the 1980s sitcom “Family Ties”. Very good. “[Operator](http://www.youtube.com/watch?v=3RA4MykPm4s)” by Jim Croce does it for me (much more so than “Time In A Bottle” which isn’t particularly sad to me, just treacly in a way that I like), as does “[Old Friends/Bookends](http://www.youtube.com/watch?v=spM4yYEPXQ8)” by Simon and Garfunkel. A Cole Porter song “So In Love”, already rather haunting in its intensity, was given a tragic twist that will always remain in my mind when [k.d. lang sang it](http://www.youtube.com/watch?v=D6Ye9G3HEsQ) with a video for “Red, Hot + Blue”, a fundraiser for AIDS research in the early 1990s. The video depicted someone going through the motions of putting away the belongings of a lover who’d just passed away. Turning that song of desperate love into one of mourning is devastating. I haven’t heard it in that context but thinking of Roberta Flack’s version of “[The First Time Ever I Saw Your Face](http://www.youtube.com/watch?v=hOFrGbuUqnQ)” as a farewell would also be gut-wrenching. ---
**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 13, 2011, 4:47pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/153 "2011-05-13T16:47:25Z")
> [@Aeris](#): > > I feel like this song could go either way though. If you watch it in the Ken Burns Civil War doc then yeah it’s sad but if you listen to it on it’s own, it’s not so sad. Agreed. This is what I meant, but failed to say. > [@Aeris](#): > > Maybe I’m just saying this in order to justify me using it for my wedding coming up. I will be walking down the aisle to this song. Nah, you’re right. That will be a beautiful wedding piece. Unsolicited advice: Wear rubber-soled shoes in case the aisles are wet-- your guests will already be feeling emotional, and that song will open the floodgates. Have a good one, and congratulations. ---
**Author:** ![Chefguy](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/chefguy/32/138_2.png) [@Chefguy](https://boards.straightdope.com/u/Chefguy)\ **Post date:** [May 13, 2011, 5:23pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/154 "2011-05-13T17:23:05Z")
[Holding Back the Years](http://www.youtube.com/watch?v=uVecxL7rjAE), Simply Red ---
**Author:** ![Alma](https://avatars.discourse-cdn.com/v4/letter/a/ecd19e/32.png) [@Alma](https://boards.straightdope.com/u/Alma)\ **Post date:** [May 13, 2011, 6:54pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/155 "2011-05-13T18:54:52Z")
> [@Carmady](#): > > Lots of sad songs here, but the saddest I’ve ever heard is Holocaust by Big Star. [Yes](http://www.youtube.com/watch?v=vsQ977u8Wuk), that’s the one I thought of too. His voice is heartbreaking. ---
**Author:** ![beagledave](https://avatars.discourse-cdn.com/v4/letter/b/6de8d8/32.png) [@beagledave](https://boards.straightdope.com/u/beagledave)\ **Post date:** [May 13, 2011, 7:10pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/156 "2011-05-13T19:10:32Z")
Richard Shindell’s Wisteria. There are no good YouTube clips of his songs (they are all crappy cell phone recordings). At least the audio on [this version](http://www.youtube.com/watch?v=iQeyWQL5LSc) is not too bad. ---
**Author:** ![beagledave](https://avatars.discourse-cdn.com/v4/letter/b/6de8d8/32.png) [@beagledave](https://boards.straightdope.com/u/beagledave)\ **Post date:** [May 13, 2011, 7:18pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/157 "2011-05-13T19:18:06Z")
[Here is a stream of Shindell’s Wisteria.](http://www.we7.com/#/song/Richard-Shindell/Wisteria) ---
**Author:** ![Gabing\_Gaboing](https://avatars.discourse-cdn.com/v4/letter/g/b38774/32.png) [@Gabing\_Gaboing](https://boards.straightdope.com/u/Gabing_Gaboing)\ **Post date:** [May 13, 2011, 11:33pm UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/158 "2011-05-13T23:33:39Z")
Hands down, for me it’s \*He’s My Son \*by Mark Schultz. I can’t link it right now, but I wouldn’t if I could because just a tidbit would do me in. It’s a prayer by a father of a very ll boy, and you can feel his desperation, fear, confusion, and pain. ---
**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 14, 2011, 2:58am UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/159 "2011-05-14T02:58:40Z")
Softly and tenderly jesus is calling…calling for you and for me… ---
**Author:** ![cornflakes](https://avatars.discourse-cdn.com/v4/letter/c/9d8465/32.png) [@cornflakes](https://boards.straightdope.com/u/cornflakes)\ **Post date:** [May 14, 2011, 3:34am UTC](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126/160 "2011-05-14T03:34:14Z")
If “saddest” can be bent to mean “most depressing”, then I’d say James Baker singing [“Ain’t No More Cane.”](http://www.youtube.com/watch?v=h6RetScHMjo) [Previous page](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126.md?page=7) [Next page](https://boards.straightdope.com/t/the-saddest-songs-you-ever-heard/581126.md?page=9)