Chris Knight, Jason Isbell, Steve Earle, Turnpike Troubadours, Cody Jinks, Tyler Childers, Colter Wall, Lucero
All great Americana / Folk Rock / Outlaw artists who have meaningful music most would call country that has nothing to do with pavement princess trucks, shitty beer, racism, or military worship. Quite a few of these artists have songs with anti establishment themes or have made statements against conservativism at some point, as far as I am aware. Classic outlaw country is also full of artists who were hippie / fuck the state types before corporations co-opted the genre
I’m not claiming to be an expert on the personal affairs or beliefs of any of these artists and I’ve removed other artists I didn’t mention from my library after learning some unsavory things. I do know Sleeping On The Blacktop, his most popular song, makes several literary juxtapositions about class and ideology in the south, one in particular about a rich white confederate type woman spitting on the working class people in a region of the appalachians that traditionally opposed the confederacy and slavery.
Would be a very odd to also play songs supporting confederate ideals at the same time, but some people do some real mental gymnastics with their views