Most Depressing Love Song of all Time?

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.

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

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.

uh, the above should read three… the play is depressing enough that I added a third at no extra charge.

James Taylor actually topped himself with “Long Ago and Far Away” off the Mud Slide Slim album.

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)

Jewel “Pieces of You” CD = Music to slit your wrists by

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

-Buckets of Rain

and

-If You See Her Say Hello

Both from Bob Dylan’s Blood on the Tracks.

A song about lost love:

  • For No One, The Beatles
    And now what is closer to an actual “love song” - yet just as sad…
  • Save Me, Aimee Mann

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.

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.

Ah, so many good suggestions already! I’ll offer a few more.

Ah, melancholy.

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.

It just needs more cowbell!

“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.

Especially for the way it fully exploits use of the cowbell.

Ahhhh! Somebody got there first!

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

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.