That is a request from Bill Russell, a loyal MR reader, and yes I will get soon to more of your requests. I’m no expert, but my picks are as follows:
1. Hank Williams Sr., get both discs and don’t look back.
George Jones and Bob Willis and Merle Haggard are all in my view somewhat overrated.
3. Louvin Brothers, Tragic Songs of Life (some call it bluegrass), Dolly Parton, Dock Boggs, Patsy Cline, the essential Johnny Cash (there’s lots of it), and the country/gospel of Elvis Presley. Dylan’s country music is good but is not his strongest suit.
Arguably the best songs of Ryan Adams (alas they are scattered but "Amy" and "La Cienega Just Smiled" are two places to start; does anyone know a more general sourcing?) are as good as anything in the genre. I like Lucinda Williams as well plus Shelby Lynne, most of all I Am Shelby Lynne.
Alternatively, the best collections from the 20s and 30s are mind-blowingly good; for instance try American Primitive on John Fahey’s Revenant label, or the Harry Smith collections. That’s some of the best American music period though in some ways the blues shouts are closer to rock and roll than to country.
I might add the whole list comes from someone who was initially allergic to country music, so if that is you give some of these recommendations a try. Just think of it as White Man’s Blues.