So you’re sitting in a small kind of smoky club in New York City called The Bitter End. Up on stage is a guy who just a few months prior was spending his days trudging through the snow delivering mail in a Chicago suburb. He’s unassuming, nervous, maybe even a little awkward. He’s playing his songs, just him and an acoustic guitar, and then this figure steps out of the shadows.

He does the same thing on Angel from Montgomery, written for the perspective of a lonely middle -aged woman in a stagnant marriage. Or Hello and There, capturing the quiet tragedy of aging. And Paradise, about the environmental destruction of his parents’ Kentucky hometown by coal companies. How does a 24 -year -old vehicle mechanic summon the lived experience to write about an elderly person fading away.

• Right, because this isn’t just a story about a guy writing good songs
• That tension, you know, between his working class reality and the polished music machine is the smine of his entire career
• After that first open mic, the audience reaction was so visceral that the club offered him a paying gig on the spot
• Roger Ebert wanders into the fifth peg, hears Prine, and is so moved, he writes his very first printed music review