Saddest songs

Trick question b/c with music it's so depending on state of mind, the favorite song always changes from time to time, so does the saddest song.
Nick Cave, Bob Dylan, Tom Waits all have sad songs and I cant remember the title of any one of them...But I think maybe Vic Chesnutt had them all covered, but he didn't exactly sing ballads.
Mazzy Star? Not sure they were sad, just melancholic.

I'm a bad music lover. I have sheitsloads of music but never bother learning names of artists or their songs... I just listen to it all.
Push the sky away , Flowers in December, Five string serenade...
 
Ingemisco quam tam...


Luciano Pavoratti YouTube


I groan as a guilty one,
and my face blushes with guilt;
spare the supplicant, O God.
You, who absolved Mary Magdalen,
and heard the prayer of the thief,
have given me hope, as well.
My prayers are not worthy,
but show mercy, O benevolent one,
lest I burn forever in fire.
Give me a place among the sheep,
and separate me from the goats,
placing me on your right hand.
 
Gordon Lightfoot - If you could read my mind

"And if you read between the lines,
You'd know that I'm just trying to understand
The feelings that you lack."


The Midnight - Synthetic

"Left who I was back there with you
Maybe I died and I kept movin'
In a body made of plastic and glue
I'm still breathing, but I'm synthetic...
Nothing human left in me"
 
Without You - Harry Nilsson
I was 16 and had a crush on a blonde goddess who was way out of my league.
Went to see Son of Dracula (starring Harry Nilsson!) at the local theatre with her, where during the course of the evening she told me that we would not be more than friends.
Somehow, this song stays with me from that evening many years ago, and whenever I hear it I feel a little pang, down deep.
 
#170

Since my father died, this song has become a personal anthem when I miss someone close.

Such as my eldest son, soon to be 8, who I've not seen in nearly 2 months now.

Thank you.

I'm off to noodle it badly on guitar and get the verses all mixed up, as usual.