Within weeks, Goodman had Prine added to his gig at New York's Bitter End where he was seen by Atlantic Records exec Jerry Wexler. In short order, Wexler signed Prine and shipped him down to Memphis to record his astonishing 1971 debut.
Prine's Atlantic years produced his sophomore album "Diamonds in the Rough," the equally impressive "Sweet Revenge," the commercially designed, but brutally honest "Common Sense."
Although Prine's commercial success with these albums was less than the label might have hoped, Prine's mailbox was filling up with royalties earned from his peers recording his songs.
From his very first album, other artists recognized Prine as a singular writing talent. He found his songs being covered by a broad spectrum of other singer/songwriters, including the Everly Brothers, Bette Midler and Joan Baez.
At a time when Prine had determined to do something different with his music - a direction hinted at with the rockier, huskier rhythms of "Common Sense" - he signed with Asylum who also had something different in mind for Prine.
After giving Asylum the beautiful and somewhat conventional "Bruised Orange," Prine wanted to access the rockabilly and country roots sound he loved as a teenager in Maywood, Ill.
In quick succession, Prine tossed off "Pink Cadillac" and "Storm Windows" (the former recorded in Memphis and produced by the family Phillips - father Sam, brothers Knox and Jerry, the latter recorded at Muscle Shoals and produced by Barry Beckett), a pair of albums that were the antithesis of the slick, shiny SoCal singer/songwriter ethic that Asylum was expecting.
Following "Storm Windows'" 1980 release, Prine and Asylum mutually agreed to end their relationship.
Flirting with the idea of abandoning music altogether, Prine and friend Al Bunetta decided to launch their own independent label, Oh Boy Records, named after the Buddy Holly song. Beyond the control and self-serving advice of the major label system, Prine suddenly began to enjoy some modest yet honest commercial success.
After the heartening sales of his initial Christmas single, Prine recorded the well-regarded "Aimless Love" in 1984 and followed it up with the bluegrass-tinged "German Afternoons" in 1986.
"German Afternoons" earned Prine his very first Grammy nomination, a feat he then matched with his first live album, entitled appropriately enough "John Prine Live," two years later.
By this time, Prine was ready for a breather. His second marriage had just dissolved and, weary of upper level label shenanigans, he had rebuked a Sony offer to buy Oh Boy. After touring to support the live album, Prine withdrew for awhile to consider his options.
In 1991, Prine decided to pursue the path that Asylum had tried to force on him 10 years before. He hooked up with Heartbreakers bassist Howie Epstein and concocted a well-produced, star-studded pop/folk album, "The Missing Years."
The title referred to the song "Jesus, the Missing Years," where Prine postulated what Christ might have been up to between puberty and crucifixion, but it might just as easily have been a sly reference to his recent predilection for taking longer and longer times between albums.
"The Missing Years" was a stone cold hit. The album notched sales of 250,000 units, a phenomenal amount for an indie, and Prine was nominated for his third Grammy, this time taking the win for Best Contemporary Folk Album.
Four years later, Prine and Epstein hooked up again for "Lost Dogs & Mixed Blessings," garnering good reviews and yet another Grammy nod.
By this time, Prine had married his third wife, Fiona, who he had met while touring in Ireland in the late '80s. By the time Prine was touring to support "Lost Dogs," he had become a first-time father at the age of 49; a second child arrived 10 months later.
Prine conceived the idea for "In Spite of Ourselves" and set out to realize his vision when the cancer diagnosis momentarily derailed his life and career.
Fate intervened once again, as George Strait took his version of Prine's "I Just Want to Dance With You" to number one on the country charts, the royalties for which more than covered Prine's medical expenses. He finished the acclaimed "In Spite of Ourselves" and was surprised at the warm reception that it received.
"I didn't expect people to hate it, but I didn't expect them to embrace it like they did just because it only had one song on it that I wrote," says Prine. "I thought, 'You can't get away with that.' But when people liked it as much as they did, I felt really good because a project like that every once in awhile really keeps you fresh. You play music because you like to and not because you want to show off your latest song. There's a lot of songs I like to sing, and I like to sit around with buddies and just play. I'd like to be able to make another record like that sometime and to think that that one got accepted is really good. I won't take advantage of it and do it too often, but every once in awhile."