Episode Details

He won a Grammy for country music, then handed his major label a sleazy synth-rock album paired with a dystopian Japanese anime film on Netflix — and walked away leaving a million dollars in unrecouped debt. Sturgill Simpson might be the only star in country music history who deliberately torched his own career at its peak.

His road there was never conventional: a Kentucky railroad yard manager in his 30s who self-funded his debut album, battled depression, burnout, and a substance abuse relapse, and called himself an anarchist while Nashville tried to put him in a box. By the time he retired the Sturgill Simpson name to make funk records as Johnny Blue Skies, he had proven that absolute artistic autonomy beats fame.

• Was managing a railroad yard in his 30s before his wife pushed him to risk music again

• Self-funded 2013 debut High Top Mountain, named for the cemetery where his family is buried

• Fulfilled his label contract with the synth-rock album Sound & Fury and a dystopian Netflix anime

• Retired his own name, acted in a Scorsese film, and reemerged as funk artist Johnny Blue Skies