Saddest songs

I come and stand at every door - The Byrds
The Mortal Coil version is even more sad.

Favourite sad songs:
I'd say everyting sung by Russian Tanya Bulanova - a few examples:
Tolko ti (Only you)
Sinee more (Blue ocean)
This one can rip my heart our
Kolibelnaya (Lullaby)

Irina Allegrova, another of the great Russian artists sang this song:
Ya tebya otvoyo (I will win you back)

Two more very sad songs from Russia:
Nautilus Pompilius - Krylya (Wings)

A sad and very frightening as it sort of replays the feelings and fear people in USSR felt during the Stain repression:
Splin- Romance

Will pick something more Western stuff later.
 
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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.