Songs that Make You Sad: Are You Ready To Be Heartbroken

Bruce Springsteen - Brilliant Disguise, My Hometown
Weezer - Butterfly
Steven Wright - Evie
Neil Young - A Man Needs a Maid
The Pretty Things - Office Love/Cries of a Midnight Circus/Trust
Cyndi Lauper - Sally's Pigeons
The Flaming Lips - Mr. Ambulance Driver/Do You Realize?
The Marmalade - Reflections of my Life
Liz Phair - F$%# and Run
Cat Stevens - Trouble
The Easybeats - Falling off the Edge of the World
Counting Crows - Murder of One
Radiohead - Fake Plastic Trees
The Kinks - Celluloid Heroes
The Shirelles - Will You Love Me Tomorrow?
Big Star - Holocaust
Everclear - Heroin Girl/Wonderful/Monster
Brandi Carlile - That Wasn't Me
Rick Springfield - My Father's Chair
Melanie - Some Say (I Got Devil)
Jewel - I'm Sensitive, Foolish Games

 

Another from Spiritualized / J. Spaceman. “Rated X”

If memory was written down,
I'd cut it up,
And cross it out,
'Cause memory holds the hurt inside,
All the pain,
And all the lies,
And you might think,
The past is through,
But the past goes right on through,
And memory holds the hurt inside,
Regret creeps up on you,
So put your hand into my hand,
And baby we'll forget,
That life had even started,
Before our hands had met.

 

'Love Don't Care (Whose Heart It Breaks)' by Earl Thomas Conley places blame on the unfair feeling called love for a failed relationship.

I can still remember
Every time I see her, I go back in time
And lose my mind
Yeah, I'm a good pretender
I just can't believe her heart's no longer mine
It's so unkind

 

'That Just About Does It' by Vern Gosdin tells the story of a relationship which is past the point of rescue.

Every night you go to bed crying
There's nothing left to do when love is dying
So before the whole world knows, how we're hurting
Don't you think it's time we pull the curtains'
That just about does it, don't it
That'll just about kill it, won't it
Maybe we should call a truce
We could but what's the use
That just about does it, don't it

 

This was used as the close out song on a TV documentary about retired Russian submariners and how their once proud sailors and families were affected when the service and vessels became run down and neglected once Perestroika became "fashionable."

 

(It's Not Easy) Bein' Green.
Though originally sung by Kermit the Frog, this song has been covered by many. It starts out sad as the singer is having a crisis of confidence, but turns hopeful at the end when he accepts that being yourself is beautiful. This version by Sophie Milman is my favorite.

Some story-songs leave you saddened by the fate of the characters:

Ode to Billie Joe - Bobbie Gentry
There was a virus going 'round; papa caught it, and he died last spring
And now mama doesn't seem to want to do much of anything

The Night the Lights Went Out in Georgia - as popularized by Vicki Lawrence
Well, they hung my brother before I could say
The tracks he saw while on his way
To Andy's house and back that night were mine

Brandy (You're a Fine Girl) - Looking Glass
At night when the bars close down
Brandy walks through a silent town
And loves a man who's not around

Wildfire - Michael Martin Murphey
Oh, they say she died one winter
When there came a killing frost

And 2 songs about playing jukebox songs that make the singer sad:
Hey Mister That's Me Up on the Jukebox - James Taylor
Wurlitzer Prize - Waylon Jennings

 

listening to 1997 Pete Ham "7 Park Avenue from Rykodisc...terribly sad how lost Pete was on the last few songs written...

no musician, rtist/group should have to suffer so much

​

 

an absolute heart-breaker. the live versions from the "prayer tour" were amazing too.

 

Few songs make me cry, but this does - every time.....

 

This is one of those heartbreakers...but not your typical sad song...
I never bothered with The Smiths in the 80s (I would have been about 13 when The Queen Is Dead was released). Now I'd say I missed out! I like that the dourness of Morrissey applies to every song, no matter the mood or subject matter. He's consistent...not to mention that his voice is beautiful.
The sad love songs are beneficial in that they give you the boost you need to keep moving. Morrissey kicks your legs out before he walks away, turns and fires one last shot into your chest -- just to make sure
"Asleep" - The Smiths (B-side, "The Boy With The Thorn In His Side"(A-side), 1985)

 

There are probably dozens and dozens of heartbreak songs I could cite. But recently there are two that come to mind that I try to avoid lest I become a blubbering mess. I was poking around the Eric Carmen/ Raspberries thread here the other day and I decided to play disc two of the essential Eric Carmen. To me, most of the songs are lightweight or schmaltzy on that disc. I will say Boats Against the Current broke my heart into pieces. I won't play that song for awhile. The other one is Springsteen's Moonlight Motel from Western Stars. That may be my favorite song he's written this century. I just turned 65. I try to limit looking back, but sometimes it's unavoidable. Just about everything my older family members have said about growing older is true. The best heartbreak or sad songs take you on a journey that you may not want to go on, but you still travel that path anyway.

 

Amy Macdonald...I Left That Body Long Ago.

If you have anyone close to you that has Alzheimer's disease this song will resonate.

I have not read the entire thread, in case this one has been mentioned already.

 

How could anyone not cry when Ole Yeller Died?

 

Matthew Sweet - Someone To Pull The Trigger

 

Michael Jackson- You Are Not Alone gets me every time..

 

Far From The Home I Love
from Fiddler On The Roof

 

Hoyt Axton's version of 500 Miles.