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Music John Prine, Nashville, USA - 20 Jun 2017

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John Prine; Ex-chicago mailman. He’s not bothered by the label

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Portrait of John Prine

This being the record industry, Prine was dropped after 1980’sStorm Windows. He took it in stride, a sign from an industry where he’d never felt particularly at home. “I used to carry a bottle of Maalox in my guitar case,”Prine told PEOPLE in 1992. “From being a mailman to traveling all around and having people writing about you — it kind of threw me for a loop.”

He eventually formed his own record label, Oh Boy, in 1984, which allowed him to engage with music at his own pace: “If my refrigerator broke down, I’d go out and sing and then I’d buy a refrigerator,” he explained. Part of his patchwork presence in the music world is his relationship with his own muse: “My music is very unplanned out,” he noted to PEOPLE. “Sometimes I just haven’t got any idea of how to write a song. It’s like I never did it before. It’s not like a job that you find in the want ads.”

Prine called the ’80s his “bachelor years.” He’d amble around various Nashville haunts and drink with other music luminaries of varying levels of fame, like Townes Van Zandt and Guy Clark. He eventually met his third wife, Fiona Whelan, in 1988 in Ireland, but the two kept in touch and eventually married in 1993.

Prine’s two sons, Jack and Tommy, were shortly born within a year of each other, and Prine also adopted Whelan’s son Jody from a previous marriage. This was all on the heels of his biggest commercial success (at least until last year’sThe Tree of Forgiveness): 1991’sThe Missing Years, which picked up a Grammy andsold almost 250,000 copies.

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John Prine

Prine’s stabilized personal life took a turn in 1996, when a lump in his neck he’d been ignoring turned out to be Stage III squamous cell cancer. A surgery forever altered both his appearance — a large chunk of his neck was excised — and his singing voice. But he doggedly worked to improve his impacted instrument, and the attendant rush of press coverage and renewed interest following his recovery let him capitalize on the album he rebounded with, 1999’sIn Spite of Ourselves.

He kept going, pushing re-recorded versions of his older songs and country standards, before 2005’sFair & Square, his first album of original material since 1995. He subsequently wentanotherround with cancer in 2013, this time of the lung, and after a uniquely songwriter-y recovery regime —jogging up and down the stairs, then grabbing his guitar and singing— hit the road six months after his surgery.

Prine, who always seemed a little more like a good-natured uncle than a Nashville hellraiser, has become a well-regarded legend among younger country stars. “I’m not sure I will ever be able to grasp the depths of John’s fearlessness when it comes to his art,”Miranda Lamberttold PEOPLE in 2016when the pair recorded the country standard “Cold, Cold Heart” for his duet albumFor Better,or Worse.

He met another duet partner from that album, Kacey Musgraves, when she first moved to Nashville in 2008. “This little girl and her friend came up and said they wanted to take me out to the parking lot and get me high!”Prine told PEOPLE in 2016. “I said, ‘I really appreciate it, but I have to go do a show!’ And then Kacey dropped a cassette in my pocket and on the cassette was one of the first songs she ever wrote called ‘Burning One with John Prine’ — and it’s a really good song!” (Prine “completely turned my songwriting world upside down,” Musgraves told PEOPLE.)

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Up for another three Grammys this year forThe Tree of Forgiveness, Prine has kept his sly sense of humor, and even adapted it to 21st-century methods of delivery:

Up for inclusion in both the the Songwriters’ Hall of Fame and the Rock and Roll Hall of Fame in 2017,Prine joked to CBS,“It took some of ’em 45 years to get the joke!” The punchline stuck, in any case:The Tree of Forgiveness,with its low-key arrangements and Prine’s scratchy voice foregrounded, became his most successful album ever, reaching No. 5 on theBillboardHot 100. “At 71-years-old,”Prine’s own website wrote in April 2018, 10 days after the album’s release, “John Prine just had his best sales week since Nielsen Music began tracking and verifying sales starting in 1991.” “In all likelihood,” it continued, “last week was John Prine’s best sales week of his entire career.”

So again, Prine’s careerdoeshave something of a conventional arc: Under-appreciated craftsman toils in a tough industry, finds family and stability late in life, weathers health crises and delivers the album of his career. It’s unlikely, though, that this proposed biopic would end, asTree of Forgivenessdoes, with a shambling start-and-stop song called“When I Get to Heaven”that refers to critics as “syphilitic parasitics” and details Prine’s plans for the afterlife: “I’m gonna get a cocktail, vodka and ginger ale / yeah I’m gonna smoke a cigarette nine miles long.” Referring again to the “joke” of his late-stage success, Prine joked to CBS that “Some people are getting it now. And I’m around to reap the benefits.”

source: people.com