"Big Iron" was part of the start of a one page (and a half - wah) story. That and High Plains Drifter. Alas, the story vanished in a puff of ones and zeros leaving the HDD. WAH!!!
Michael Martin Murphy did a series of albums centered on "Cowboy music", including the obvious "sung around the campfire at summer camp" songs. He also includes some true old material. Although not, strictly speaking, cowboy material, he includes a few good poems (e.g., Cowboy Logic and which is the cowboy in the pickup). "Wildfire" has an interesting premise, but that d*** guitar lick after almost every phrase should be stuffed into the player's ears until he(?) screams for mercy. "Carolina in the Pines", etc. are nice pop. NTL, like his tenor.
Chris LeDeux's got some great material and was a been there, done that, say d*** near anything he wants. I don't think I've heard a true "oldie but goodie" but IMHO he has tight grip on the sound.
One of the earworms is "Born to be a Cowoy". It had me at "The painted walls of Palo Duro". I like the MMM version but I recommend listening to the YouTube version of [COLOR=var(--ytd-video-primary-info-renderer-title-color, var(--yt-spec-text-primary))]
R W Hampton, "Born to Be a Cowboy"[/ color]
Robert Earl Keen is supposed to be great stuff. I just can't deal with his voice. I just can't.
Lyle Lovett is also modern but worth a serious listen.
Finally, even Garth Brooks, scores with "Night Rider's Lament" and a couple of others - "Wolves" maybe.
Fave singer: tell me which day is it, and I'll tell you which one it is.