I've been listening to the Amazon Music "Texas Country" station lately that plays Flatland Cavalry, Randy Rogers, Wade Bowen, etc. MUCH better than any of the Top 40 country radio that I can't stand.

I can go with a lot of what's been mentioned already for old stuff, and I'd add (for content and a good hook) 2 Lee Ann Womack songs:

I May Hate Myself In The Morning
https://www.youtube.com/watch?v=gS35hISn7x0

Twenty Years and Two Husbands Ago
https://www.youtube.com/watch?v=h0vQ5qt3JbI