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

The come out and play line gets me every time..

 

Beautiful

Israel Kamakawiwo'ole BOSS

 

George Jones - He Stopped Loving Her Today.

 

For me it's Bob Dylan's Dream. Reminiscing about younger days and close friends you never see again...that one gets to me. Also I Was Young When I Left Home.

 

There is no shortage of heartbreak and despair in this man's work.

 

Check ...on both songs! The latter has a particularly sad tone to it.

 

”Martha” and ”Ruby’s Arms” by Tom Waits get me everytime...

 

Nearly anything by Mark Kozelek but i’m gonna go with his Katy Song by Red House Painters. A beautiful song about his girlfriend, all the more heartbreaking as she would go on to die in 2003.
“Without you is all my life amounts to”

 

Vern Gosdin | Chiseled In Stone

 

John Doe | Twin Brother

 

That is probably my favourite Elton song, strangely off one of my least favourite Elton albums, and yes it is a tear provoking song, if you allow it in.

 

''I'm So Lonesome I Could Cry'' - Hiram King "Hank" Williams, although he didn't write the lyrics to the song... allegedly.

 

God Only Knows makes me very sad usually. It's heartbreaking to listen to. (the beautiful In My Life can have a similar effect if in the right mood)
Another song that makes me sad is Point Blank by Bruce Springsteen (as well as The River); the song is devastating.

Wedding Bells by Hank Williams is another sad one
What Becomes Of The Brokenhearted by Jimmy Ruffin

 

Regardless , Hank wrote enough about heartbreak and despair. More than enough...

 

Raspberries-Starting Over
Bread-Everything I Own
Bread-If
5th Dimension-One Less Bell To Answer

 

Hmmm... I see this thread title was 'altered'
Hmm..

 

"Skyway" by The Replacements. Breaks my heart every time I hear it.

 

There are 25 threads on this including a very recent one I believe.

 

Now that is a sad lyric ! I wept upon reading it.

 

A window into the thoughts of someone suffering from serious depression, sung and performed so convincingly that I almost felt like I should find a way to reach out to the band and offer my support!

 

As I walk this land of broken dreams
I have visions of many things
But happiness is just an illusion
Filled with sadness and confusion........

 

Fountain of Sorrow--Jackson Browne

When you see through love's illusions, there lies the danger
And your perfect lover just looks like a perfect fool
So you go running off in search of a perfect stranger
While the loneliness seems to spring from your life
Like a fountain from a pool

 

It may seem a strange one, but @Tuco reminded me that this track is pretty up there in the emotive stakes.
It seems quite innocuous at first.
Yes the music is beautiful, and it twists into the little dancing section and it could be about anything. As an instrumental you kind of glide along the melody that has a certain melancholy, and only the title gives you a clue that it has something deeper going on.
It's a beautiful little tune that has almost a dance feel at places, but it has this disarming ethereal synth come over the top ... Like I say a very pretty, innocuous tune ... and then it kicks in. The sad, reflective vocal "Life isn't every thing ...." like a meditation to the lost, almost an apology . Great piece of writing.

 

Dogs by Pink Floyd. Yes, you could say Sheep is also sad, but the problem is I know so many dogs. Apparently they know no other way. And that's sad.

Masters Of War - Dylan

Strange Fruit - Billie Holiday.

China Doll - Grateful Dead