I have to agree with most of the people that said Johnny Cash. A lot of his songs were so sad and depressing. The songs "I Hung My Head" and "Hurt" are so deeply emotional that it makes me want to cry when listening to him say the words.
Another song that I think that is pretty sad (or maybe just haunting) is from one of my top 10s. It's the song called "My Mind's Eye" by Sirenia. Here is part of the lyrics.
If you are down
I will come to chain you to the ground
And penetrate your mind.
If you are lost *if only you are lost*
I'll be there to break your trust
And ravage all your lust for life, my love
You will never realize
What darkness lies inside
inside my mind.
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