John Prine

John Prine was working as a mail carrier in Chicago when he started performing at open mics, and his self-titled 1971 debut arrived with a set of songs — about aging, war, addiction, and rural loneliness — written with an economy and dark humor that immediately drew comparisons to Bob Dylan, comparisons Prine himself found faintly embarrassing given how quickly he'd written most of the material.

He went on to record for five decades, developing a devoted following among songwriters even when his commercial profile stayed modest, and his plainspoken, detail-driven approach to character and place became a direct influence on generations of Americana and folk-adjacent artists. Prine's ability to be simultaneously funny and devastating within the same song, often the same verse, remained the signature of his writing throughout his career.