# 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:** 3
**Author:** ![Baker](https://avatars.discourse-cdn.com/v4/letter/b/bb73d2/32.png) [@Baker](https://boards.straightdope.com/u/Baker)\ **Post date:** [March 11, 2014, 11:02pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/41 "2014-03-11T23:02:30Z")
“Cat’s in the Cradle” ---
**Author:** ![the\_diego](https://avatars.discourse-cdn.com/v4/letter/t/7bcc69/32.png) [@the\_diego](https://boards.straightdope.com/u/the_diego)\ **Post date:** [March 11, 2014, 11:19pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/42 "2014-03-11T23:19:58Z")
“Empty Chairs” by Don Maclean. Thread question answered. ---
**Author:** ![Gangster\_Octopus](https://avatars.discourse-cdn.com/v4/letter/g/a8b319/32.png) [@Gangster\_Octopus](https://boards.straightdope.com/u/Gangster_Octopus)\ **Post date:** [March 11, 2014, 11:27pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/43 "2014-03-11T23:27:35Z")
"Tears in Heaven’ by Eric Clapton, especially knowing what it is about. ---
**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:** [March 11, 2014, 11:38pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/44 "2014-03-11T23:38:43Z")
[Strange Fruit](http://www.youtube.com/watch?v=h4ZyuULy9zs). Billie Holiday. ---
**Author:** ![Ethilrist](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/ethilrist/32/4604_2.png) [@Ethilrist](https://boards.straightdope.com/u/Ethilrist)\ **Post date:** [March 11, 2014, 11:55pm UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/45 "2014-03-11T23:55:45Z")
“Into the West,” sung by Annie Lennox on the final credits to _Return of the King._ ---
**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:** [March 12, 2014, 12:02am UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/46 "2014-03-12T00:02:19Z")
I know plenty of sad songs, have sung some myself but this is the latest uber-sad song I’ve heard. [Pray For Newtown - Sun Kil Moon](http://www.youtube.com/watch?v=r5dWBPsru-Y) The whole album, called Benji, is sad, painful even, in its rawness, bittersweetness. I recommend it. ---
**Author:** ![ZipperJJ](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/zipperjj/32/211_2.png) [@ZipperJJ](https://boards.straightdope.com/u/ZipperJJ)\ **Post date:** [March 12, 2014, 12:17am UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/47 "2014-03-12T00:17:59Z")
[Skates](http://www.youtube.com/watch?v=-2voANkDn1Q&feature=kp) by Hayden. Song about working in a department store, helping a man purchase some ice skates. Turns out the guy wanted ice skates so he can go rescue his drowned wife from the river when it freezes over, since he can’t swim. That’s my classic go-to saddest song, but I heard Band of Horses’ [No One’s Gonna Love You](http://www.youtube.com/watch?v=cuZo7pLnL7c) (“more than I do”) a few years ago and it crushes me every time I hear it. But for personal reasons…it’s not actually that sad. ---
**Author:** ![InternetLegend](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/internetlegend/32/13154_2.png) [@InternetLegend](https://boards.straightdope.com/u/InternetLegend)\ **Post date:** [March 12, 2014, 12:20am UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/48 "2014-03-12T00:20:41Z")
[Casimir Pulaski Day](http://www.youtube.com/watch?v=9EzeW5KoPUI) by Sufjan Stevens. The [lyrics](http://songmeanings.com/songs/view/3530822107858541824/) start with “Goldenrod and the 4-H stone/The things I brought you when I found out/You had cancer of the bone” and it goes from there. The rather upbeat melody just makes it all sadder. ---
**Author:** ![pulykamell](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/pulykamell/32/3166_2.png) [@pulykamell](https://boards.straightdope.com/u/pulykamell)\ **Post date:** [March 12, 2014, 12:30am UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/49 "2014-03-12T00:30:59Z")
> [@Labrador\_Deceiver](#): > > That’s a cover of a 1964 hit by J. Frank Wilson and the Cavaliers, for what it’s worth. Yeah. And around that general time period, there was a whole spate of “dead teenager” songs. See “Laurie (Strange Things Happen),” “Patches,” “Teen Angel,” “Dead Man’s Curve,” “Tell Laura I Love Her,” etc. ETA: The wonderful Steve Goodman [hits three of these songs here](http://www.youtube.com/watch?v=j3WVT8gCmDk), after starting out with “Born To Be Wild.” (Start at about 3:00 if you want to skip the “Born to Be Wild” part.) ---
**Author:** ![suranyi](https://avatars.discourse-cdn.com/v4/letter/s/e36b37/32.png) [@suranyi](https://boards.straightdope.com/u/suranyi)\ **Post date:** [March 12, 2014, 1:03am UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/50 "2014-03-12T01:03:30Z")
“Dust Bowl” by 10,000 Maniacs. ---
**Author:** ![P-man](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/p-man/32/3606_2.png) [@P-man](https://boards.straightdope.com/u/P-man)\ **Post date:** [March 12, 2014, 1:12am UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/51 "2014-03-12T01:12:15Z")
> [@kenobi\_65](#): > > Roy Orbison’s [In the Real World](http://www.youtube.com/watch?v=c-8Fxu8TEH0). It’s not “she broke up with me”, but “we’re deeply in love, but there’s no way that it’s going to work out.” A very sad theme, made sadder due to some personal relevance for me. I used to think “Windsurfer” (guy falls in love with somebody he never has a chance with) from the same album was sad when the same thing happening to me was fresher in my memory, but after almost 18 year of marital bliss it doesn’t have the same effect on me. “Tears in Heaven” might be close for me now; I lost a grandparent around the time it came out. ---
**Author:** ![Telemark](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/telemark/32/372_2.png) [@Telemark](https://boards.straightdope.com/u/Telemark)\ **Post date:** [March 12, 2014, 1:13am UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/52 "2014-03-12T01:13:43Z")
> [@Ulfreida](#): > > [Kilkelly Ireland](https://www.youtube.com/watch?v=QRHQAtKbRTk). Beat me to it. ---
**Author:** ![standingwave](https://avatars.discourse-cdn.com/v4/letter/s/9de0a6/32.png) [@standingwave](https://boards.straightdope.com/u/standingwave)\ **Post date:** [March 12, 2014, 1:18am UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/53 "2014-03-12T01:18:37Z")
"Without You’ by Badfinger as recorded by Harry Nilsson in 1971: [![]( " - YouTube") ](https://www.youtube.com/watch?v=eywk8zK43I4) ---
**Author:** ![XOldiesJock](https://avatars.discourse-cdn.com/v4/letter/x/ec9cab/32.png) [@XOldiesJock](https://boards.straightdope.com/u/XOldiesJock)\ **Post date:** [March 12, 2014, 1:24am UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/54 "2014-03-12T01:24:16Z")
“The Last Time I Saw Her Face” by Gordon Lightfoot. Can’t even get by the first verse before tears well up. [Gordon Lightfoot - The Last Time I Saw Her Face - YouTube](https://www.youtube.com/watch?v=uEccY6hMdrk) ---
**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:** [March 12, 2014, 1:30am UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/55 "2014-03-12T01:30:08Z")
“The Kids” by Lou Reed ( from the album _Berlin_ ). Should depress even the most psychotically cheerful person ;). ---
**Author:** ![Clothahump](https://avatars.discourse-cdn.com/v4/letter/c/51bf81/32.png) [@Clothahump](https://boards.straightdope.com/u/Clothahump)\ **Post date:** [March 12, 2014, 1:33am UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/56 "2014-03-12T01:33:32Z")
Oh, where to start… [Darcy Farrow](https://www.youtube.com/watch?v=sRqU-CEN-D4) [Early Mornin’ Rain](https://www.youtube.com/watch?v=0OCnHNk2Hac) (link is to PP&M’s cover) Probably the saddest of the bunch, though, is Jackson Browne’s[In The Shape of a Heart](https://www.youtube.com/watch?v=AWIJ8RAcsHQ) ---
**Author:** ![dzeiger](https://avatars.discourse-cdn.com/v4/letter/d/46a35a/32.png) [@dzeiger](https://boards.straightdope.com/u/dzeiger)\ **Post date:** [March 12, 2014, 1:43am UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/57 "2014-03-12T01:43:21Z")
The video’s a little goofy, but Buck Dharma’s [Your Loving Heart](https://www.youtube.com/watch?v=0HBs2eUlb0A) is pretty sad. ---
**Author:** ![Try2B\_Comprehensive](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/try2b_comprehensive/32/65_2.png) [@Try2B\_Comprehensive](https://boards.straightdope.com/u/Try2B_Comprehensive)\ **Post date:** [March 12, 2014, 1:44am UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/58 "2014-03-12T01:44:34Z")
I always thought The [Ballad of Ira Hayes](https://www.youtube.com/watch?v=6gvtQA4gbRw) was up the list. [The Great Dust Storm Disaster](https://www.youtube.com/watch?v=vvI7BmuUBXU) is as sad as it gets, but probably too hokey/old-timey for a lot of people. I was getting choked up over [Cortez the Killer](https://www.youtube.com/watch?v=m-b76yiqO1E&feature=kp) the other day, but I wonder who else will wait that long for it or see it that way. It is supposed to be about Cortez, but spends almost the entire song mythologizing the Natives, on and on, until the last line says apparently all there is to say about Cortez: _what a killer_. The Native Apocalypse is basically left to your imagination. What can I say? Dead Indians make me sad. ---
**Author:** ![Battle\_Pope](https://avatars.discourse-cdn.com/v4/letter/b/4bbf92/32.png) [@Battle\_Pope](https://boards.straightdope.com/u/Battle_Pope)\ **Post date:** [March 12, 2014, 1:53am UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/59 "2014-03-12T01:53:58Z")
Mentioned already but [Eric Bogle’s version of “The Band Played Waltzing Matilda”](http://youtu.be/WG48Ftsr3OI) is a downer. If you like horses [The Last Parade](http://youtu.be/LzMls4tz50A) (a sung version of a Banjo Patterson poem) should do the trick as well. ---
**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:** [March 12, 2014, 2:14am UTC](https://boards.straightdope.com/t/saddest-song-you-know/683461/60 "2014-03-12T02:14:47Z")
[The Best Ever Death Metal Band In Denton](https://www.youtube.com/watch?v=4IsXKMkDAMQ) by the Mountain Goats is another contender in my opinion. [Previous page](https://boards.straightdope.com/t/saddest-song-you-know/683461.md?page=2) [Next page](https://boards.straightdope.com/t/saddest-song-you-know/683461.md?page=4)