If you have Netflix, check out the Norm MacDonald show episode with lesser-known (than Willie, Johnny, Waylon, etc) country legend Billy Joe Shaver as the guest. He does a few songs in between the interview / commentary and while I'd heard his music before this particular performance is just him and a guy playing acoustic, and it's sublimely good, IMO.
Only old-ass guys with tons of miles behind them sound like this, IMO, a bit like George Jones in the Aaron Lewis song, old man gravelly voice that's still sweet sounding somehow. Some say Billie Joe Shaver is the "godfather of Outlaw Country", and his songs have been recorded by Bob Dillon and other more famous names in the (original/good) country scene.
This video isn't from the Norm MacDonald show, and it's with a full band, but it'll convey the gist well enough to maybe help make it worth it to specifically watch that episode: