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Alone Again, Naturally by Gilbert O'Sullivan - the bleakest ever hit pop record?

How about a big band accompaniment set to a flamenco rhythm?

Delilah - Tom Jones

Jones narrates the song as a betrayed lover who spies his woman in silhouette on a window blind as she makes love to another man. Although he realises that she is no good for him, he becomes temporarily insane. Waiting until her paramour leaves, at the break of day, he knocks on the door, which she opens, only to laugh in his face. He then stabs her to death. Realising this murderous act, the betrayed lover begs her forgiveness before the police come to break down the door and take him away.

I saw the light on the night that I passed by her window
I saw the flickering shadow of love on her blind
She was my woman
As she deceived me I watched and went out of my mind

My, my, my Delilah
Why, why, why Delilah
I could see, that girl was no good for me
But I was lost like a slave that no man could free

At break of day when that man drove away I was waiting
I crossed the street to her house and she opened the door
She stood there laughing
I felt the knife in my hand and she laughed no more

My, my, my Delilah
Why, why, why Delilah
So before they come to break down the door
Forgive me Delilah I just couldn't take anymore
 
Unfortunately a suitable segue to this :-



Googling reveals the story is even more gruesome than I'd thought.
 
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