So much of what I would select, such as the Bogle, Brel, Portishead, Tabor, Emmylou and so on has already been posted here.
So I will add:
Bogle: No Man's Land (obviously), plus "Singing the Spirit Home" and "Little bits of Paper" (unsure of the title), which contains the hook line "My father died in Summer..."
Neil Young: Keep on Rockin' in the Free World
Mahler: Symphony number 6, especially the last moments. Essentially, Man goes through life being kicked by fate. Every time things look good, it is merely fate lining him up for another kick, so eventually he says "no more, I quit, I.m just lying down and giving up"
So it puts the boot in on the ground.
Beethoven: Symphony number 7. The greatest shout of pure joy ever written.
Oysterband: Coal not Dole running into Bells of Rhymney
Sibelius: Symphony 3 for its opening and finale, 5 for its warmth, and 4 for its devastatingly bleak soundscape. You think Tchaikovsky 6 is sad?