# Most Depressing Love Song of all Time? **URL:** \ **Category:** Cafe Society\ **Created:** [February 13, 2003, 3:05am UTC](https://boards.straightdope.com/t/most-depressing-love-song-of-all-time/154743 "2003-02-13T03:05:12Z")\ **Posts on this page:** 20\ **Page:** 3
**Author:** ![ianzin](https://avatars.discourse-cdn.com/v4/letter/i/ed655f/32.png) [@ianzin](https://boards.straightdope.com/u/ianzin)\ **Post date:** [February 13, 2003, 9:13pm UTC](https://boards.straightdope.com/t/most-depressing-love-song-of-all-time/154743/41 "2003-02-13T21:13:04Z")
If you want the best, you gotta go to the best. Just about anything from Sinatra’s classic 1954 album _In The Wee Small Hours_ would surely win the ‘most depressing love song’ prize. It’s practically an aural suicide note. Any one of the first four tracks (In the Wee Small Hours of the Morning, Mood Indigo, Glad to Be Unhappy, I Get Along Without You Very Well) could send the listener to the nearest tall building. ---
**Author:** ![Shodan](https://avatars.discourse-cdn.com/v4/letter/s/9f8e36/32.png) [@Shodan](https://boards.straightdope.com/u/Shodan)\ **Post date:** [February 13, 2003, 10:01pm UTC](https://boards.straightdope.com/t/most-depressing-love-song-of-all-time/154743/42 "2003-02-13T22:01:49Z")
Nothing Compares 2 U - Sinead O’Connor And the Thunder Rolls - Garth Brooks "And he knows that she knows, And the thunder rolls. The thunder rolls, And the lightning strikes And another love grows cold." Excuse me while I go commit suicide. Regards, Shodan ---
**Author:** ![Sampiro](https://avatars.discourse-cdn.com/v4/letter/s/2acd7d/32.png) [@Sampiro](https://boards.straightdope.com/u/Sampiro)\ **Post date:** [February 13, 2003, 10:25pm UTC](https://boards.straightdope.com/t/most-depressing-love-song-of-all-time/154743/43 "2003-02-13T22:25:28Z")
I’ve fought my gayness long enough: I can’t go on… time for the showtunes: SOMEWHERE (West Side Story [I once read that Sondheim wrote these lyrics for a gay lover who was dying, but I’ve never found a cite so I can’t speak for its veracity]) NOT A DAY GOES BY (Merrily We Roll Along) I GUESS I’LL MISS THE MAN (Pippin) SOMETHING WONDERFUL (The King and I) I WON’T SEND ROSES I PROMISED YOU A HAPPY ENDING (both from Mack & Mabel) BEFORE I GAZE AT YOU AGAIN (Camelot) A LITTLE DROP OF RAIN (Les Mis) EVERYTHING’S AS IF WE NEVER SAID GOODBYE (Sunset Blvd.- it’s a lovesong to a psychotic woman’s youth rather than a person, but still) The entire score of Miss Saigon. TELL ME TO GO (Martin Guerre) And finally the two most depressing showtune/love-songs: WITHOUT YOU I’LL COVER YOU (reprise) YOUR EYES (all three from RENT) On a similar note, while it’s not a showtune I always found Cat Stevens’ TROUBLE sad because I associate it with the end of Harold & Maude. ---
**Author:** ![Sampiro](https://avatars.discourse-cdn.com/v4/letter/s/2acd7d/32.png) [@Sampiro](https://boards.straightdope.com/u/Sampiro)\ **Post date:** [February 13, 2003, 10:27pm UTC](https://boards.straightdope.com/t/most-depressing-love-song-of-all-time/154743/44 "2003-02-13T22:27:31Z")
uh, the above should read three… the play is depressing enough that I added a third at no extra charge. ---
**Author:** ![Exapno\_Mapcase](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/exapno_mapcase/32/1051_2.png) [@Exapno\_Mapcase](https://boards.straightdope.com/u/Exapno_Mapcase)\ **Post date:** [February 13, 2003, 10:57pm UTC](https://boards.straightdope.com/t/most-depressing-love-song-of-all-time/154743/45 "2003-02-13T22:57:12Z")
James Taylor actually topped himself with “Long Ago and Far Away” off the Mud Slide Slim album. > [@](#): > > To love is just a word I’ve heard when things are being said > Stories my poor head has told me cannot stand the cold > And in between what might have been and what has come to pass > A misbegotten guess alas and bits of broken glass The melody is beautiful, but far sadder than “Fire and Rain” However, since the saddest song in the entire universe is the Cowboy Junkies’ version of Hank Williams’ “I’m So Lonesome I Could Cry” and since that is a love song, then the award for saddest love song ever goes to: The Cowboy Junkies. (The Trinity Session album) ---
**Author:** ![DeVena](https://avatars.discourse-cdn.com/v4/letter/d/dec6dc/32.png) [@DeVena](https://boards.straightdope.com/u/DeVena)\ **Post date:** [February 13, 2003, 11:03pm UTC](https://boards.straightdope.com/t/most-depressing-love-song-of-all-time/154743/46 "2003-02-13T23:03:41Z")
Jewel “Pieces of You” CD = Music to slit your wrists by ---
**Author:** ![MC\_Master\_of\_Ceremonies](https://avatars.discourse-cdn.com/v4/letter/m/bb73d2/32.png) [@MC\_Master\_of\_Ceremonies](https://boards.straightdope.com/u/MC_Master_of_Ceremonies)\ **Post date:** [February 13, 2003, 11:12pm UTC](https://boards.straightdope.com/t/most-depressing-love-song-of-all-time/154743/47 "2003-02-13T23:12:44Z")
I have to agree with Skip here, _Love Will Tear Us Apart_ by Ian Dury: When the routine bites hard and ambitions are low And the resentment rides high but emotions won’t grow And we’re changing our ways, taking different roads Then love, love will tear us apart again Why is the bedroom so cold Turned away on your side? Is my timing that flawed, our respect run so dry? Yet there’s still this appeal That we’ve kept through our lives Love, love will tear us apart again Do you cry out in your sleep All my failings expose? Get a taste in my mouth As desperation takes hold Is it something so good Just can’t function no more? When love, love will tear us apart again ---
**Author:** ![Enginerd](https://avatars.discourse-cdn.com/v4/letter/e/bcef8e/32.png) [@Enginerd](https://boards.straightdope.com/u/Enginerd)\ **Post date:** [February 13, 2003, 11:18pm UTC](https://boards.straightdope.com/t/most-depressing-love-song-of-all-time/154743/48 "2003-02-13T23:18:22Z")
> [@](#): > > Life is sad > Life is a bust > All ya can do is do what you must. > You do what you must do and ya do it well, > I’ll do it for you, honey baby, > Can’t you tell? -_Buckets of Rain_ and > [@](#): > > Sundown, yellow moon, I replay the past > I know every scene by heart, they all went by so fast > If she’s passin’ back this way, I’m not that hard to find > Tell her she can look me up if she’s got the time. -_If You See Her Say Hello_ Both from **Bob Dylan’s** _Blood on the Tracks_. ---
**Author:** ![joshmaker](https://avatars.discourse-cdn.com/v4/letter/j/a587f6/32.png) [@joshmaker](https://boards.straightdope.com/u/joshmaker)\ **Post date:** [February 14, 2003, 12:07am UTC](https://boards.straightdope.com/t/most-depressing-love-song-of-all-time/154743/49 "2003-02-14T00:07:11Z")
A song about lost love: > [@](#): > > Your day breaks, your mind aches > There will be time when all the things she said will fil your head > You won’t forget her > > And in her eyes you see nothing > No sign of love behind the tears > Cried for no one > A love that should have lasted years! - _For No One_, The Beatles And now what is closer to an actual “love song” - yet just as sad… > [@](#): > > You look like a perfect fit > For a girl in need of a tourniquet > > But can you - save me > Come on and - save me > If you could - save me > From the ranks of the freaks > Who suspect they could never love anyone - _Save Me_, Aimee Mann ---
**Author:** ![InTransit](https://avatars.discourse-cdn.com/v4/letter/i/e47774/32.png) [@InTransit](https://boards.straightdope.com/u/InTransit)\ **Post date:** [February 14, 2003, 12:17am UTC](https://boards.straightdope.com/t/most-depressing-love-song-of-all-time/154743/50 "2003-02-14T00:17:09Z")
> [@](#): > > \*Originally posted by Gyan9 \* > \*\*I don’t know if you can call _U2_’s **One** depressing. \*\* Not sure I’d consider “One” a love song, but it certainly could be construed as one. I’m taking depressing love song to be of the unrequited love sort. With that… “Pictures of You” – The Cure “I’ll Sail This Ship Alone” – Beautiful South (though some of the lines crack me up) “Heart of the Matter” – Don Henley “Kissing a Fool” – George Michael “Devotion” – Tracy Chapman “When We Dance” – Sting “But Not For Me” – G & I Gershwin “Better Be Home Soon” & “Distant Sun” (_I don’t pretend to know what you want, but I offer love_")-- Crowded House I have _way_ to many of these types of songs in my collection. ---
**Author:** ![InTransit](https://avatars.discourse-cdn.com/v4/letter/i/e47774/32.png) [@InTransit](https://boards.straightdope.com/u/InTransit)\ **Post date:** [February 14, 2003, 12:21am UTC](https://boards.straightdope.com/t/most-depressing-love-song-of-all-time/154743/51 "2003-02-14T00:21:20Z")
> [@](#): > > \*Originally posted by MC Master of Cermonies \* > **I have to agree with Skip here, _Love Will Tear Us Apart_ by Ian Dury:** You mean Ian Curtis/Joy Division? So many things that Ian/Joy Division did was dark. I love them anyway (or maybe because of that). I’m thinking that I want _Atmosphere_ played at my funeral. That, or _Ding, Dong the Witch is Dead._ ---
**Author:** ![Coldfire](https://avatars.discourse-cdn.com/v4/letter/c/a587f6/32.png) [@Coldfire](https://boards.straightdope.com/u/Coldfire)\ **Post date:** [February 14, 2003, 12:23am UTC](https://boards.straightdope.com/t/most-depressing-love-song-of-all-time/154743/52 "2003-02-14T00:23:15Z")
Ah, so many good suggestions already! I’ll offer a few more. > [@](#): > > _Hand in Hand_ by **Dire Straits** > Now you and me go parallel together and apart > And you keep your perfect distance and it’s tearing in my heart > And you never feel the distance > You never try to cross no line > Now it’s another dirty river and another dirty scar > And I don’t know who’s kissing you and I don’t know where you are > So far from home don’t you think of me sometime > > If I’ve been hard on you I never chose to be > I never wanted no-one else > I tried my best to be somebody you’d be close to > Hand in hand like lovers are supposed to > [@](#): > > _The Wild Rose_ by **Nick Cave and Kylie Minogue** > (KYLIE:) > On the third day he took me to the river > He showed me the roses and we kissed > And the last thing I heard was a muttered word > As he knelt above me with a rock in his fist > > (NICK:) > On the last day I took her where the wild roses grow > She lay on the bank, the wind light as a thief > And I kissed her goodbye, said: “All beauty must die” > And I lent down and planted a rose between her teeth > > (KYLIE:) > They call me The Wild Rose > But my name was Elisa Day > Why they call me it, I do not know > For my name was Elisa Day > [@](#): > > _Fairytale of New York_ by **The Pogues ft. Kirsty McCal** > > - I could have been someone > > - Well so could anyone > - You took my dreams from me > - When I first found you > > - I kept them with me babe > - I put them with my own > - Can’t make it all alone > - I’ve built my dreams around you Ah, melancholy. ---
**Author:** ![slamf666](https://avatars.discourse-cdn.com/v4/letter/s/f19dbf/32.png) [@slamf666](https://boards.straightdope.com/u/slamf666)\ **Post date:** [February 14, 2003, 12:26am UTC](https://boards.straightdope.com/t/most-depressing-love-song-of-all-time/154743/53 "2003-02-14T00:26:32Z")
Maybe not so much depressing as inappropriate, but how about “Don’t Fear the Reaper”? Would you want this supposedly romantic song dedicated to you? ---
**Author:** ![Mothchunks](https://avatars.discourse-cdn.com/v4/letter/m/a587f6/32.png) [@Mothchunks](https://boards.straightdope.com/u/Mothchunks)\ **Post date:** [February 14, 2003, 1:25am UTC](https://boards.straightdope.com/t/most-depressing-love-song-of-all-time/154743/54 "2003-02-14T01:25:42Z")
Actually, I find “Don’t Fear the Reaper” curiously catharctic and uplifting. ---
**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:** [February 14, 2003, 1:34am UTC](https://boards.straightdope.com/t/most-depressing-love-song-of-all-time/154743/55 "2003-02-14T01:34:10Z")
> [@](#): > > \*Originally posted by Mothchunks \* > \*\*Actually, I find “Don’t Fear the Reaper” curiously catharctic and uplifting. \*\* It just needs _more cowbell_! ---
**Author:** ![Rubystreak](https://avatars.discourse-cdn.com/v4/letter/r/e5b9ba/32.png) [@Rubystreak](https://boards.straightdope.com/u/Rubystreak)\ **Post date:** [February 14, 2003, 1:35am UTC](https://boards.straightdope.com/t/most-depressing-love-song-of-all-time/154743/56 "2003-02-14T01:35:40Z")
“Black,” by Pearl Jam: “I know someday you’ll have a beautiful life, I know you’ll be a star in somebody else’s sky–but why, oh why, can’t it be mine?” “In Spite of Me,” by Morphine: “Late last night I saw you in my living room/ You seemed so close but yet so cold/ For a long time I thought that you’d be coming back to me/ Those kind of thoughts can be so cruel/ So cruel/ And I know you did it all in spite of me.” Been there, done that, trying NOT to go there tomorrow. ---
**Author:** ![NDP](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/ndp/32/55_2.png) [@NDP](https://boards.straightdope.com/u/NDP)\ **Post date:** [February 14, 2003, 1:36am UTC](https://boards.straightdope.com/t/most-depressing-love-song-of-all-time/154743/57 "2003-02-14T01:36:35Z")
> [@](#): > > Maybe not so much depressing as inappropriate, but how about “Don’t Fear the Reaper”? Would you want this supposedly romantic song dedicated to you? > > … > > Actually, I find “Don’t Fear the Reaper” curiously catharctic and uplifting. Especially for the way it fully exploits use of the cowbell. ---
**Author:** ![NDP](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/ndp/32/55_2.png) [@NDP](https://boards.straightdope.com/u/NDP)\ **Post date:** [February 14, 2003, 1:37am UTC](https://boards.straightdope.com/t/most-depressing-love-song-of-all-time/154743/58 "2003-02-14T01:37:36Z")
Ahhhh! Somebody got there first! ---
**Author:** ![Pashnish\_Ewing](https://avatars.discourse-cdn.com/v4/letter/p/8797f3/32.png) [@Pashnish\_Ewing](https://boards.straightdope.com/u/Pashnish_Ewing)\ **Post date:** [February 14, 2003, 3:26am UTC](https://boards.straightdope.com/t/most-depressing-love-song-of-all-time/154743/59 "2003-02-14T03:26:23Z")
My vote goes to **No Doubt** ’s **Don’t Speak**. _Don’t speak I know just what you’re saying So please stop explaining Don’t tell me 'cause it hurts_ My heart breaks for lovely Gwen every time I hear it. And I’ll second **Heart of the Matter** , although I find it uplifting as well. I agree that it should be about forgivenes, even if you’re ex doesn’t love you anymore. Pash ---
**Author:** ![fizgig](https://avatars.discourse-cdn.com/v4/letter/f/f04885/32.png) [@fizgig](https://boards.straightdope.com/u/fizgig)\ **Post date:** [February 14, 2003, 3:44am UTC](https://boards.straightdope.com/t/most-depressing-love-song-of-all-time/154743/60 "2003-02-14T03:44:58Z")
_I Hope That I Don’t Fall in Love with You_ by Tom Waits makes me want to dive to the bottom of a whiskey glass, as does his _House Where Nobody Lives_. [Previous page](https://boards.straightdope.com/t/most-depressing-love-song-of-all-time/154743.md?page=2) [Next page](https://boards.straightdope.com/t/most-depressing-love-song-of-all-time/154743.md?page=4)