Dean's midweek martini-worthy image got me thinking about the kind of country music that I like, which honestly isn't a lot. I do have some examples, mostly from Johnny Cash. Gram Parsons and Emmylou Harris, pictured on Dean's blog performing Love Hurts. (Couldn't find live performance that would embed well.)
From the movie O Brother Where Art Thou?, the Soggy Bottom Boys perform Man of Constant Sorrow.