Sturgill Simpson is the singer that Nashville tapped as the next face of outlaw country only to have him fully reject that classification and for the most part, Nashville in general.

Simpson comes from the depressed coal country of eastern Kentucky and the town of Jackson. It was there he got his first exposure to music, watching friends of his parents play bluegrass together. After his family moved to Versailles Simpson had a rocky high school experience and landed in the Navy and various odd jobs before returning to the Lexington area. From there he released his first two albums, with the second “Meta Modern Sounds in Country Music” gaining a Grammy nomination.

In 2016 Sturgill Simpson released “A Sailor’s Guide to Earth”, his first self-produced album. A non-conventional country record, it still gained a Grammy nomination and won the Best Country Album Grammy. Initially Simpson had planned to stay off the road after releasing the album but instead he toured to capitalize on the Grammy win.

Out on tour rather than at home with his young children, Simpson was miserable: “Honestly, there was a point in 2017 where I thought I was just going to just go away,” he said plainly. Simpson’s music career didn’t begin in earnest until his mid-30s — he knew what life was like before it, and was mentally prepared for life after it.

2019’s “Sound and Fury” completely left the Nashville model and featured a funky rock sound and was accompanied by a $1 million dollar anime film. This year, Simpson has gone back to revisit some of his earlier material but in a bluegrass format on “Cuttin’ Grass, Vol. 1”.