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In the late 1980s, John Prine’s records weren’t selling like they once did. So his longtime manager, Al Bunetta, made a big move, mortgaging his house to raise enough money to hire Howie Epstein—the bass player for Tom Petty & The Heartbreakers—to produce Prine’s most ambitious album yet.

The result is 1991’s The Missing Years, which includes guest appearances from Petty, John Mellencamp, Bruce Springsteen and Bonnie Raitt, and features some of the strongest material of Prine’s career. Just listen to the rambling “The Sins of Memphisto”, which includes the couplet: “Sally used to play with her hula hoops/Now she tells her problems to therapy groups.”

Throughout The Missing Years, Prine pulls from his own life. On “All the Best”—written as his second marriage was falling apart—he confesses how hard it is to truly wish the best for an ex-lover. “Everything is Cool”, meanwhile, finds him emerging from relationship rubble to start again with a positive attitude. It all leads to “Jesus the Missing Years”, a surreal story imagining what Jesus Christ did between the ages of 12 and 33—the mysterious 18-year-gap in Christ’s life that’s not documented in the Bible. According to Prine’s song, JC saw Rebel Without a Cause, then went home and invented Santa Claus (he also traveled a lot, and discovered The Beatles).

Prine later said he was afraid to sing “Jesus the Missing Years” after completing it: “I thought they were going to look at me and say, ‘You’ve done it. You’ve crossed the line. You need the straightjacket.’ But if I let it sit for a couple weeks and it still affects me, it’s something I would like to hear somebody say, then I figure, my instinct is as good as a normal person.” His instincts proved right: “Jesus the Missing Years” became a fan favourite, and The Missing Years would win Prine his first Grammy.

© Apple Music