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-fun ...