And basically any track from Johnny Cash's American V: A Hundred Highways. Yes, it was finished posthumously. But on every single track he sounds so sad, lonely, worn out, and old. Definitely recommended for those depressing nights spent awake and alone.
Sadly one Sunday, I waited and waited
With flowers in my arms, for the dream I'd created
I waited 'til dreams like my heart were all broken
The flowers were all dead and the words were unspoken
The grief that I knew was beyond all consoling
The beat of my heart was a bell that was tolling
Saddest of Sundays
Then came the Sunday when you came to find me
They brought me to church and I left you behind me
My eyes would not see the one I wanted to love me
The earth and the flowers were forever above me
The bell tolled for me and the wind whispered 'never'
But you I have loved and I'll love you forever
Last of all Sundays