# Saddest love song ever. **URL:** \ **Category:** Cafe Society\ **Created:** [August 14, 2007, 3:33am UTC](https://boards.straightdope.com/t/saddest-love-song-ever/415518 "2007-08-14T03:33:00Z")\ **Posts on this page:** 20\ **Page:** 3
**Author:** ![Boulter\_s\_Canary](https://avatars.discourse-cdn.com/v4/letter/b/e79b87/32.png) [@Boulter\_s\_Canary](https://boards.straightdope.com/u/Boulter_s_Canary)\ **Post date:** [August 14, 2007, 1:19pm UTC](https://boards.straightdope.com/t/saddest-love-song-ever/415518/41 "2007-08-14T13:19:21Z")
[Richard Thompson](http://www.richardthompson-music.com/song_o_matic.asp?id=211) has written a [few](http://www.richardthompson-music.com/song_o_matic.asp?id=207). ---
**Author:** ![Spice\_Weasel](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/spice_weasel/32/5435_2.png) [@Spice\_Weasel](https://boards.straightdope.com/u/Spice_Weasel)\ **Post date:** [August 14, 2007, 1:43pm UTC](https://boards.straightdope.com/t/saddest-love-song-ever/415518/42 "2007-08-14T13:43:12Z")
Gin Blossoms ‘‘Found Out About You’’ is probably one of the most heartbreaking songs I know of. What gets me is the slightly bitter edge to it. _Months roll past the love that you struck dead Did you love me only in my head? The things you said and did to me Seemed to come so easily The love I thought I’d won you’d give for free…_ I also came in here to nominate Reba McEntire’s version of ‘‘Cathy’s Clown,’’ a song about a woman who has to stand by and watch the man she loves be mistreated by his significant other. _You know you’ve got to stand tall You know a man can’t crawl And when you let her tell you lies And you let em pass you by You’re not a man at all_ With Reba’s haunting voice, it always gets me. ---
**Author:** ![Mark\_Ryle](https://avatars.discourse-cdn.com/v4/letter/m/8dc957/32.png) [@Mark\_Ryle](https://boards.straightdope.com/u/Mark_Ryle)\ **Post date:** [August 14, 2007, 1:43pm UTC](https://boards.straightdope.com/t/saddest-love-song-ever/415518/43 "2007-08-14T13:43:33Z")
Burt Bacharach and Hal David’s _Walk on By_, sung by Dionne Warwick. The Bacharach music elaborates and enhances the lyrics so admirably: > [@](#): > > If you see me walking down the street > And I start to cry each time we meet > Walk on by. This is followed by a very casual, almost whistling-tune type musical bridge before the next line, indicating the singer, up to now, is still in possession of her mental equilibrium. Then comes: > [@](#): > > Foolish pride – that’s all that I have left > So let me hide the tears and the sadness you gave me > When we said goodbye On that syllable, “…bye,” a solo piano begins a dramatic three-note, downward, repeating E-D-middle C – E-D-middle C – E-D-middle C – at least a dozen times, while a female chorus chants, staccato, “Don’t’” - Stop - Don’t - Stop." [walking by] This goes on until a new verse begins, breaking the spell. The spell created by those “Don’t Stop” chants, with the relentlessly repetitive three-note piano, to me, signifies the singer’s sudden downward psychological trajectory straight into a rut the unexpected sight of this former lover has thrown her into. When I hear it, it reminds me of the way a thought will repeat and repeat in your brain, like an endless loop of tape. Walk on By is one of the saddest and most true-to-life songs, for me, and a song in which the music fits the words perfectly. ---
**Author:** ![Slypork](https://avatars.discourse-cdn.com/v4/letter/s/9fc29f/32.png) [@Slypork](https://boards.straightdope.com/u/Slypork)\ **Post date:** [August 14, 2007, 1:53pm UTC](https://boards.straightdope.com/t/saddest-love-song-ever/415518/44 "2007-08-14T13:53:32Z")
[_The Long and Winding Road_](http://www.stevesbeatles.com/songs/the_long_and_winding_road.asp) by The Beatles ---
**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:** [August 14, 2007, 1:54pm UTC](https://boards.straightdope.com/t/saddest-love-song-ever/415518/45 "2007-08-14T13:54:14Z")
Ben Folds writes some particularly sad love songs. The one that fits this thread best is perhaps [Selfless, Cold and Composed](http://benfolds.bluni.com/display.php?songid=56) come on baby, now throw me a right to the chin don’t just stare like you never cared I know you did but you just smile like a bank teller blankly telling me: “have a nice life” ---
**Author:** ![Wakinyan](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/wakinyan/32/352_2.png) [@Wakinyan](https://boards.straightdope.com/u/Wakinyan)\ **Post date:** [August 14, 2007, 1:54pm UTC](https://boards.straightdope.com/t/saddest-love-song-ever/415518/46 "2007-08-14T13:54:48Z")
Yes, _Romeo and Juliet_ is special. ---
**Author:** ![yellowval](https://avatars.discourse-cdn.com/v4/letter/y/919ad9/32.png) [@yellowval](https://boards.straightdope.com/u/yellowval)\ **Post date:** [August 14, 2007, 1:55pm UTC](https://boards.straightdope.com/t/saddest-love-song-ever/415518/47 "2007-08-14T13:55:34Z")
Travis Tritt’s [Tell Me I Was Dreaming](http://www.lyriczz.com/lyriczz.php?songid=16987) always gets me. ---
**Author:** ![Liberal](https://avatars.discourse-cdn.com/v4/letter/l/848f3c/32.png) [@Liberal](https://boards.straightdope.com/u/Liberal)\ **Post date:** [August 14, 2007, 1:56pm UTC](https://boards.straightdope.com/t/saddest-love-song-ever/415518/48 "2007-08-14T13:56:05Z")
**We All Fall In Love Sometimes** — Elton John and Bernie Taupin ---
**Author:** ![Lord\_Ashtar](https://avatars.discourse-cdn.com/v4/letter/l/7ea924/32.png) [@Lord\_Ashtar](https://boards.straightdope.com/u/Lord_Ashtar)\ **Post date:** [August 14, 2007, 2:07pm UTC](https://boards.straightdope.com/t/saddest-love-song-ever/415518/49 "2007-08-14T14:07:23Z")
_Face of Melinda_ by Opeth. The whole album it’s on is about the lead singer and his relationship with a girl named, you guessed it, Melinda. This song is about how they ran into each other after having not seen each other for a few years. The flame is still there, but she’s married. > [@](#): > > I took her by the hand to say, > “All faith forever has been washed away > I returned for you in great dismay > Come with me, far away to stay.” > > Endlessly gazing in nocturnal prime > She spoke of her vice and broke the rhyme > Puzzled herself with the final line, > “My promise is made but my heart is thine.” ---
**Author:** ![Butterscotch](https://avatars.discourse-cdn.com/v4/letter/b/dc4da7/32.png) [@Butterscotch](https://boards.straightdope.com/u/Butterscotch)\ **Post date:** [August 14, 2007, 2:16pm UTC](https://boards.straightdope.com/t/saddest-love-song-ever/415518/50 "2007-08-14T14:16:05Z")
Not sure about the saddest one ever, but it always gets me: [Cold day in July by the Dixie Chicks](http://www.youtube.com/watch?v=1ywD3505pH8) (Links to youtube) Her, with her head in her hands, in her barefeet, watching him drive away, ouch… ---
**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:** [August 14, 2007, 2:21pm UTC](https://boards.straightdope.com/t/saddest-love-song-ever/415518/51 "2007-08-14T14:21:23Z")
_I’m Still Here_ By \*\*Tom Waits \*_(Along with most of his other love songs). \* You haven’t looked at me that way in years You dreamed me up and left me here How long was I dreaming for What was it you wanted me for_ ---
**Author:** ![xnylder](https://avatars.discourse-cdn.com/v4/letter/x/bbce88/32.png) [@xnylder](https://boards.straightdope.com/u/xnylder)\ **Post date:** [August 14, 2007, 2:27pm UTC](https://boards.straightdope.com/t/saddest-love-song-ever/415518/52 "2007-08-14T14:27:55Z")
_Famous Blue Raincoat_, especially as covered by Tori Amos. _Yes, and thanks, for the trouble you took from her eyes I thought it was there for good so I never tried._ ---
**Author:** ![Spoke](https://avatars.discourse-cdn.com/v4/letter/s/a88e57/32.png) [@Spoke](https://boards.straightdope.com/u/Spoke)\ **Post date:** [August 14, 2007, 2:30pm UTC](https://boards.straightdope.com/t/saddest-love-song-ever/415518/53 "2007-08-14T14:30:04Z")
A couple of very blue songs: **"Almost Blue"** - **Elvis Costello** (The woman he’s with is a pale imitation of the woman he still wants. And nobody’s happy about it.) _Almost blue Almost doing things we used to do Theres a girl here and shes almost you Almost all the things that your eyes once promised I see in hers too Now your eyes are red from crying Almost blue_ **"Once in a Very Blue Moon"** - **Nanci Griffith** _I found your letter in my mailbox today You were just checking if I was okay And if I miss you, well, you know what they say It’s just Once in a Very Blue Moon_ ---
**Author:** ![villa](https://avatars.discourse-cdn.com/v4/letter/v/bc79bd/32.png) [@villa](https://boards.straightdope.com/u/villa)\ **Post date:** [August 14, 2007, 3:21pm UTC](https://boards.straightdope.com/t/saddest-love-song-ever/415518/54 "2007-08-14T15:21:15Z")
[Whiskey Lullaby](http://www.lyrics007.com/Brad%20Paisley%20Lyrics/Whiskey%20Lullaby%20(Featuring%20Alison%20Krauss)%20Lyrics.html) - Brad Paisley & Allison Krauss. “She put him out, like the burning end of a midnight cigarette.” I mean, who hasn’t been there… ---
**Author:** ![Guy\_Incognito](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/guy_incognito/32/3920_2.png) [@Guy\_Incognito](https://boards.straightdope.com/u/Guy_Incognito)\ **Post date:** [August 14, 2007, 3:25pm UTC](https://boards.straightdope.com/t/saddest-love-song-ever/415518/55 "2007-08-14T15:25:26Z")
Another vote for “Romeo and Juliet” by Dire Straits. What a song! Even the guitar hook near the end of the song that mirrors the “You and me babe – how about it?” lyric packs a wallop for me. You know the part I mean. Makes me think of a lonely guy calling out to his girl from the front steps of her building, knowing that she’ll never answer him. I’d like to toss in “Coming Up Close” by 'Til Tuesday. A great song about a one night stand that felt like something much more: “I thought just for an instant we could see the future, I thought for once we knew what really was important” “Coming up close, everything sounds like “welcome home”. Come home. Come on home.” Aimee Mann writes a hell of a song. Don’t let anyone tell you differently ---
**Author:** ![Gail](https://avatars.discourse-cdn.com/v4/letter/g/b9e5f3/32.png) [@Gail](https://boards.straightdope.com/u/Gail)\ **Post date:** [August 14, 2007, 3:32pm UTC](https://boards.straightdope.com/t/saddest-love-song-ever/415518/56 "2007-08-14T15:32:18Z")
_Something’s Always Wrong_ by Toad the Wet Sprocket–always gets me _I Can’t Make You Love Me_ by Bonnie Raitt _Back 2 Good_ by Matchbox 20 _Ten Years Gone_ by Led Zeppelin…sad, and it has a great guitar hook! ---
**Author:** ![NailBunny](https://avatars.discourse-cdn.com/v4/letter/n/ecae2f/32.png) [@NailBunny](https://boards.straightdope.com/u/NailBunny)\ **Post date:** [August 14, 2007, 3:32pm UTC](https://boards.straightdope.com/t/saddest-love-song-ever/415518/57 "2007-08-14T15:32:33Z")
_Into My Arms_ by Nick Cave & the Bad Seeds. The lyrics are so simple, to just write them out really doesn’t do them justice unless you can hear the emotion behind Nick’s voice when he sings them. Every time I’ve seen him live, there’s pretty much not a dry eye in the house during this song. And then the video is just a close up on various people’s faces as they start crying. Jesus! ---
**Author:** ![Dead\_Badger](https://avatars.discourse-cdn.com/v4/letter/d/848f3c/32.png) [@Dead\_Badger](https://boards.straightdope.com/u/Dead_Badger)\ **Post date:** [August 14, 2007, 4:00pm UTC](https://boards.straightdope.com/t/saddest-love-song-ever/415518/58 "2007-08-14T16:00:48Z")
[QUOTE=An Gadaí] _I’m Still Here_ By \*\*Tom Waits \*\*(Along with most of his other love songs). [/QUOTE] Ah, you beat me to it. So I shall submit [Fish & Bird](http://youtube.com/watch?v=7PGtmLvEdaM) from the same LP. Oh, and that performance? I was there for that. Oh hey, the whole thing is on YouTube! Frickin’ _awesome_! ---
**Author:** ![SaharaTea](https://avatars.discourse-cdn.com/v4/letter/s/e9a140/32.png) [@SaharaTea](https://boards.straightdope.com/u/SaharaTea)\ **Post date:** [August 14, 2007, 4:22pm UTC](https://boards.straightdope.com/t/saddest-love-song-ever/415518/59 "2007-08-14T16:22:53Z")
I second 'Til Tuesday’s \*\*[Coming Up Close](http://www.youtube.com/watch?v=b7xX3lQ3qms). \*\* It’s really a perfect song. I also adore Tom Waits’ \*\*“San Diego Serenade.” \*\* A beautiful song about regret and not knowing what you’ve got til it’s gone. > [@](#): > > I never saw the white line, til I was leaving you behind > I never knew I needed you til I was caught up in a bind > I never spoke I love you til I cursed you in vain, > I never felt my heartstrings until I nearly went insane. ---
**Author:** ![Spice\_Weasel](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/spice_weasel/32/5435_2.png) [@Spice\_Weasel](https://boards.straightdope.com/u/Spice_Weasel)\ **Post date:** [August 14, 2007, 4:24pm UTC](https://boards.straightdope.com/t/saddest-love-song-ever/415518/60 "2007-08-14T16:24:42Z")
> [@](#): > > Into My Arms by Nick Cave & the Bad Seeds. The lyrics are so simple, to just write them out really doesn’t do them justice unless you can hear the emotion behind Nick’s voice when he sings them. Every time I’ve seen him live, there’s pretty much not a dry eye in the house during this song. I just did a YouTube search. Holy Crap! That song has me reduced to a globbering mash of putty. [Previous page](https://boards.straightdope.com/t/saddest-love-song-ever/415518.md?page=2) [Next page](https://boards.straightdope.com/t/saddest-love-song-ever/415518.md?page=4)