I have almost no knowledge of country music. I live in alabama, so naturally there are a ton of country stations on the radio, but it's all garbage and I can't stand listening to the radio anyway. too many damn commercials, etc. The Dead is about as country as I get but I love em either way I do have a Johnny Cash album or two but to be perfectly honest I can't say his stuff has ever done that much for me. perhaps in time though, just not yet... I prefer albums as a whole to songs or compilations but if it's really good I'll check it out. how about some essentials?
If you are interested in diving into some oldies but goodies try downloading Time Life Classic Country. If you're looking for something newer try something like Old Crow Medicine Show's O.C.M.S album. Hank Williams Sr. is essential country so check that out too.
I love OCMS also good and my fav are TRAMPLED BY TURTLES! Good Old War, Cross Canadian Ragweed for more country.
Check out some john hartford. He's witty and knowledgable about old folk songs that he has collected. He can be a bit goofy at times but he has a lot of really amazing stuff. If you can get your hands on a copy try a john hartford album called "aereo plain".
"Steam Powered Aeroplane" John Hartford was amazing live, and a walking songbook. onto country (may include oldtime and various bluegrass strains): I really love when Ricky Skaggs joins young bands at fests. He's a strong performer, and his material is definitely into country. (probably why that is the only time I hear him) I saw Sweet Sunny South at Four Corners Folk. Single mic harmonies from the pre-television radio era. Really really good stuff. Look for Travis Linville out of Oklahoma (same "movement" as Cross Canadian Ragweed) Red Dirt Rangers Jimmy LaFave Willis Allen Ramsey (hi allison!) Greg Brown Santa Cruz Band (blend of a lot of southwestern music) Sam Bush. search Youtube for "Circles" Nitty Gritty Dirt Band and just because I love his playing, Tommy Emmanuel Look for Woodsongs Radio Hour (which is also televised) to sample musicians.