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

Camera Obscura- Lloyd I’m Ready To Be Heartbroken.
Biz Markee- Just A Friend.
Hank Williams- There’s A Tear In My Beer.
Three Dog Night- Easy To Be Hard.
Bobby Vinton- Mr Lonely.

 

This one's always done it for me since I was old enough to understand the passing of time:

 

Another one:

 

Paradise just makes my stomach sink. Truly one of the saddest Prine songs IMO.

 

So many great songs on this thread. I have been on an Alanis Morissette kick of late, and several of her songs come to mind. Her voice and the musical accompaniment get to me every time I listen to them...
1. "That Particular Time" -
I've always wanted for you what you've wanted for yourself
and yet I wanted to save us high water or hell
and I kept on ignoring the ambivalence you felt
and in the meantime I lost myself
in the meantime I lost myself
I'm sorry I lost myself -I am

2. "Simple Together" -
You've been my soulmate and then some
I remembered you the moment I met you
With you I knew god's face was handsome
With you I saw final expansion
This loss is numbing me
It pierces my chest
And I can't stop dropping everything

3. "This Grudge" -
I want to be big and let go
Of this grudge that's grown old
For the life of me I've not known
How to rest this bygone
I wanna be soft and resolved
Clean of slate and released
I wanna forgive for the both of us.

now I have to go get a tissue........

 

OMG.....This song also used to get to me all the time, and I never wanted anyone to know I liked it!

 

The impact of so many of Chilton's Big Star songs has a lot to do with with his plaintive delivery.

 

Eva Cassidy - “Fields of Gold” on “Songbird”. It’s like she’s right there reaching out to us from the great beyond.

You'll remember me when the west wind moves upon the fields of barley...

 

“Your day breaks
Your mind aches”




Here comes the tears

 

For no one
She's leaving home
Elanor rigby

 

Cats in the cradle

 

Just about anything from Townes Van Zandt.

 

This Old House - CSNY
Gets me every time.

 

The Girl from the North Country- Dylan/Cash
Bang the Drum Slowly and Michaelangelo- Both Emmylou Harris
Theme to Last Exit to Brooklyn-Mark Knopfler

 

Yes indeed. Also:

"Beautiful Boy" ~ John Lennon
"Old Brown Dog" ~ Ralph McTell
"The Rainbow Connection" ~ Kermit the Frog
"Ooh Baby Baby" ~ The Miracles
"Have You Seen Her?" ~ The Chi-Lites

 

'Boots of Spanish Leather' by Bob Dylan comes to mind.

 

The Flying Burrito Brothers - Sing Me Back Home

 

suffer little children: the smiths

 

billy bragg: saturday kid

 

“Windows and Walls” (1984) by Dan Fogelberg is definitely one of the most depressing songs I’ve ever heard.

 

In my world, this was Dan's all-time best song and I have loved it since it was brand new. The verse of "Clock on the mantle chiming the hours, must be the loneliest sound", with that clock ticking effect and then that chime in time with the melody, rips right into my heart.

 

I'm normally a happy upbeat guy, but when it comes to music, these type of sad songs have always been some of my favorite music. Being raised on Sinatra thanks to my parents and hearing all of his sad songs for so long got me started with these and then when I was around 12 or 13 and Gilbert O'Sullivan's "Alone Again Naturally" and Neil Sedaka's "Laughter In The Rain" poured out of my AM radio, I was hooked on "sad songs".

Sometimes the "sad" songs that I love don't immediately come off as "sad", as they often will disguise themselves with an upbeat melody, like this one ...



Re-watching this video, I couldn't help but notice that even Nez even gets that same "sad but happy memory" look in his eyes that I always get, when he sings my favorite line of the song ... "and still I can't stop thinking, when I hear some whistle cryin'"

 

A few from Jim Croce...

Photographs and Memories @ 0:00
Operator @ 5:02
Lovers Cross @ 23:33
These Dreams @ 46:17
Time In A Bottle @ 49:27

 

Your answer could make a great thread of its own.
Although I'm sure someone would whine it's been done before.

 

Totally agree, though I prefer the version with "When The Tigers Broke Free", which fits perfectly with the mood of the album. People get caught up with who did what, instead of just listening to the album. I prefer The Final Cut to the Wall, though the Wall has great parts, I think The Final Cut is actually the better album as a whole. It hits the target that it aims for.