Sad songs

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She danced with me and I still hold that memory
Soft and sweet and I stare up at her window
As I walk down her street, but I never made the first team
I just made the first team laugh and she never came to the phone
She was always in the bath

In the end, it took me a dictionary
To find out the meaning of unrequited
While she was giving herself for free
At a party to which I was never invited

"The Saturday Boy" Billy Bragg
 
I think Hurt is probably the most universally sad song, but from a personal perspective, it would be 'Man Of The World' by Fleetwood Mac. It was played at my uncle's funeral, and was the first time I'd ever heard it. It summed him up so perfectly, and now whenever I hear it on the radio, I burst into tears. Making me sad merely typing this post.

Not sure if it was intended to be a sad song but it sure is for me.
 

Context is everything really..... I broke up with my missus around the time of Beck's last album, to me that album is pure sadness because it fires off little nostalgic pangs and the likes, whilst 'straight to you' by Nick is associated with really good memories for me, even the Daniel Johnson song only really became 'sad' after I watched the film about him. I actually find 'Dancing Queen' very sad, there is an emptiness and loneliness about the thing, some strange melancholia

 

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