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Kentucky singer/songwriter Sturgill Simpson was in his mid-30s when he found fame as a country artist in Nashville. He had already lived a full life including a stint in the Navy, and years spent working in Salt Lake City rail yards. His outsider status in Nashville boosted his outlaw appeal.

But as time passed, Sturgill began to despise the relentless expectations of the major label system. In true rebel fashion, Sturgill has now taken back control of his career and returned to his independent roots with the release of a bluegrass album: “Cuttin’ Grass – Vol. 1 (Butcher Shoppe Sessions).”

In this interview with Rick Rubin, Sturgill explains why his bluegrass album is the purest expression of his work, why it bothers him that people often overlook the stories in his songs, and why being classified as a country artist has been, perhaps, the biggest detriment to his career.

You can find a playlist of some of our favorite Sturgill Simpson songs here.

The Hosts

Rick Rubin

In addition to being a podcast host, Frederick Jay “Rick” Rubin is an American record producer and former co-president of Columbia Records. Along with Russell Simmons, he is the co-founder…

Malcolm Gladwell

Malcolm Gladwell is co-founder of Pushkin Industries and host of the hit podcast Revisionist History. He is a journalist, a speaker, and the author of several New York Times bestsellers including The Tipping…

Justin Richmond

Justin Richmond is producer and co-host of the music podcast Broken Record with writer Malcolm Gladwell, New York Times editor Bruce Headlam, and music producer—and Def Jam co-founder—Rick Rubin. Justin…

Bruce Headlam

Bruce Headlam is one of the co-creators of the music podcast Broken Record. He worked at The New York Times for 19 years, including two years running the 50-person Video…