I've been listening to Johnny Paycheck's late sixties output on Little Darlin' records a fair bit over the past few months, and I'm still fairly surprised and / or blown away by how dark the lyrics are. I find it interesting that these cats (like Paycheck, Hank Williams, Sr and Porter Wagoner) were writing this grim shit and that this stuff was being commercially produced and released back then. I dunno, I guess it just seems unlikely when you think about the time and you sort of get this "golden era" of clean sunshiney pop and family living in your mind. But I suppose all that was on a pretty fast downturn by the time the late 60s came around.
But still, you could give someone the lyrics for like, Paycheck's "The Cave" or Hank William's "Men With Broken Hearts" and
easily persuade them that either one was written today. They might be like "Is this a Will Scheff tune?" or something

. But it's a testament to how great / timeless those guys really were as writers.
So, anytime you encounter some hipster trying to sell you on how great and dark some new post-emo, rootsy album is, and how the 20-something dude that wrote it is a visionary and must've really been through some shit in his time, you should direct them to "I Just Came to Smell The Flowers" by Porter Wagoner (1966) - A song that basically describes how he likes to hang around strangers' funerals and only feels at home around that kind of misery, or maybe Paycheck's "(Like Me) You'll recover in Time" - wherein he describes his mental degeneration after his wife left him, and how they ultimately wind up in the same mental institution. Great stuff.