John Prine's career has typically been made around the margins of country music, but last year's Tree of Forgiveness is the hit of his career, up for three Grammys this year

In a lot of ways, John Prine has lived a very conventional life, albeit by a set of standards somewhat different from others. His is the classic “blue-collar average Joe gets discovered, kicks around the music industry, recovers from a serious illness, ages comfortably into elder statesman” story, and if Prine hadn’t insisted on bucking convention from the get-go with his wry, occasionally bleakly humorous tunes, he’d probably already have a big-budget biopic.

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But Prine defies easy categorization: Unlike a figure like Blaze Foley (given the prestige biopic last year by Ethan Hawke), Prine doesn’t have a deep bench of stories from his hell-raising years or any outsize quirks (like Foley’s duct-taping habit). He’s just got a catalog of incredible songs, some of which would cause the “proper” country establishment to choke on their grits. (“There’s a hole in daddy’s arm where all the money goes” comes to mind.)

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Prine’s biography is pretty standard: Son No. 3 to William and Verna Prine (in 1946), he grew up in Maywood, Illinois, where he acquired the Midwest accent that would further set him apart from his Nashville contemporaries. Twenty years later, he was drafted, but wound up in West Germany instead of Vietnam, “drinking beer and pretending to fix trucks,” as he told Rolling Stone in 2017. Coming back home, he worked as a mailman, until he found himself onstage in a Chicago club one night. (He’d drunkenly heckled some of the talent and wound up being dared to do better; he did and was subsequently offered a gig by the club owner.)

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“Eight years ago Prine was discovered in a Chicago pub by Kris Kristofferson,” reads PEOPLE’s earliest mention of Prine (from 1980), “but he has yet to enjoy real commercial success.” This was true, largely: Any success Prine saw in the ’70s was usually with someone else’s name attached: the Everly Brothers covered his song “Paradise,” in 1972, “Angel from Montgomery” got its first bump when Bonnie Raitt covered it in 1974, and “Hello in There” was covered by Bette Midler and Joan Baez, in 1972 and 1975, respectively. He wasn’t credited on David Allen Coe’s 1974 breakthrough hit, “You Never Even Called Me By My Name,” though he helped write it with his friend Steve Goodman. (Goodman bought Prine a vintage Wurlitzer jukebox as a thank-you.)

He’d been signed by Atlantic fairly quickly via Kristofferson’s patronage, but part of Prine’s inability to break through was his own unwillingness to be pigeonholed: He’d zig from sparse and melancholy ballads like “Sam Stone” and “Hello in There” on his 1971 to, in 1975, Memphis-influenced soul (on Common Sense, produced by the city’s legendary guitarist Steve Cropper) and then, in 1979, full-fledged rockabilly (Pink Cadillac, produced at Sun Studios by founder Sam Philips).

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This being the record industry, Prine was dropped after 1980’s Storm 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’s The Tree of Forgiveness): 1991’s The Missing Years, which picked up a Grammy and sold almost 250,000 copies.

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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’s In Spite of Ourselves.

He kept going, pushing re-recorded versions of his older songs and country standards, before 2005’s Fair & Square, his first album of original material since 1995. He subsequently went another round 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 Lambert told PEOPLE in 2016 when the pair recorded the country standard “Cold, Cold Heart” for his duet album For 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 for The 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 the Billboard Hot 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.”