Sturgill Simpson is the hard-to-classify, but always intriguing singer and songwriter who sounds like Waylon Jennings or Merle Haggard (take your choice, as both were great singers); writes about topics not often heard on contemporary country radio; has outspoken progressive politics sure to rub many country music fans the wrong way; and who has a gift for surprise…as you’ll find at the end of this Saturday Soundtrack post. (Bluegrass fans who can’t wait should just jump there first!) A native of Kentucky, the son of a secretary and a Kentucky State Trooper, Simpson is the first male on his mother’s side of the family to not work in a strip mine or deep mine. Nonetheless, that blue collar, hard working sensibility comes through with every song he writes and every note he sings. He is a Navy veteran who speaks up in his songs and in interviews about the dangers of the military industrial complex. In a famous Facebook Live post outside the 2017 Country Music Association awards show, Simpson said, “Nobody needs a machine …