Gordon Lightfoot — “The Wreck of the Edmund Fitzgerald”
From the album Summertime Dream.

The legend lives on from the Chippewa on down
of the big lake they called “Gitche Gumee.”
The lake, it is said, never gives up her dead
when the skies of November turn gloomy.
With a load of iron ore twenty-six thousand times more
than the Edmund Fitzgerald weigh empty,
that good ship and crew was a bone to be chewed
when the “Gales of November” came early.

Hell. Fucking. Yeah.

More music.

Fleet Foxes — “Helplessness Blues”
From the album of the same name.

I was raised up believing I was somehow unique
Like a snowflake distinct among snowflakes, unique in each way you can see
And now after some thinking, I’d say I’d rather be
A functioning cog in some great machinery serving something beyond me

More Music…

Bruce Cockburn — “Pacing the Cage”
From the album The Charity of Night

It was later covered by Jimmy Buffett for his album Beach House on the Moon.

This song makes me want to crawl into a dark closet, curl up in a fetal position and fall asleep.

Tom Waits — “Martha”

From the album Closing Time.

This is one of my go-to “sad bastard” songs.