Johnny Cash: "Hurt"
Originally a Nine Inch Nails song about Trent's addictions, transforms to a man at the end of life reflecting on all that he's lost. Lie Down. Try Not to Cry. Cry a Lot.
"Gentle on My Mind" (also a Johnny Cash cover)
About a Hobo reflecting on the woman he is/was in love with.
"You Want It Darker" Leonard Cohen
I have no words for this song. This is less sobbing tears, more that feeling of being empty and done.