Stan Rogers/Tear Jerker

This Canadian folk musician has some incredibly sad songs.

• Go listen to "Northwest Passage", then try "Barrett's Privateers".

Goddamn them all, I was told
We'd cruise the seas for American gold
We'd fire no guns, shed no tears
Now I'm a broken man on a Halifax pier
The last of Barrett's Privateers.

• "First Christmas". It's the experiences of a young man working the night shift to make ends meet, an abused teenage girl in a homeless shelter, and an old man whose family have put him in a nursing home, on their first Christmas away from home. The third verse especially can do it.
• There's also "Turnaround", used at the end of the end of the TV movie, Terry about Canada's great hero, Terry Fox. Just the chorus "Yours is the open road/The bitter song, the heavy load that I'll never share/Though the offer's still there/Every time you turn around" hits you in the heart of what a man Terry was and what we lost when he died so all too soon.
• "Harris and the Mare" is awfully goddamn sad.
• "The Last Watch" can make anyone who has made their living on a ship for any period of time break down like a child.
• Many other Rogers songs fit the bill: "White Squall", "Lock-Keeper", "MacDonnell on the Heights", "Make And Break Harbour"... the list goes on. And on.