Good songwriters can do some good stuff when they are writing what they know. Bad singwriters can crawl up their own assholes, though. Some good Americana Alt-Country ones:
Mercury in Retrograde - Sturgill Simpson takes on the realities of "success". Really the whole Sound and Fury album, though; the whole thing is just him raging at the labels and expectations people put on him as "the next Waylon Jennings."
Bible on the Dash: Life for work-a-day touring musicians. Corb Lund and Hayes Carll actually come up with something useful about a hotel Bible.
Robert Earl Keen:
My Home Ain't in the Hall of Fame. Checking out of the Nashville rat race.
What I Really Mean: Wistful realities of road life for someone at a different life phase than the one above.
The Road Goes On & On: a vicious diss track at Toby Keith's expense. REK is like the chill Democrat New-Balance Suburban Dad of brilliant Americana singer-songwriters, so he probably wouldn't speak ill of the dead, but I will. Fuck Toby Keith.