Here's one of the saddest storyteller songs I've ever heard and that I think would make a very nice lesson (great for strummers and there's some great little lead guitar in it too). "The Blizzard" (1961) by Jim Reeves.
It would fit perfectly in the "cowboy songs" section (that section is just begging to become fuller). Also, I've been missing seeing new country classics on the site... no Merle, no Waylon, no Buck, no Roy Clark, no George Jones, no Don Williams, only 1 Hank Sr. song, and so many more including the ladies. Any country classics would be most welcome. Thanks!