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.