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All these analogies do serve a purpose, I swear: they aren’t just the reasons for—and ways in which—Prine is a singular talent; together, they explain why he has always been underappreciated and lesser-known relative to his prodigious talent and wide-ranging influence on some of the greatest working songwriters. His legacy lives in their voices and songs: Bonnie Raitt has made a career-long practice of covering “Angel from Montgomery”; Jason Isbell’s thoughtful character studies and economy with language are straight out of the John Prine playbook (he also owns the Martin acoustic Prine used to write his first album); and Brandi Carlile, Sturgill Simpson, Amanda Shires, Miranda Lambert, Iris DeMent, and many other country, folk, and Americana luminaries frequently collaborate with Prine. The common parlance for such an underappreciated talent is a “songwriter’s songwriter,” but what are we really saying when we say that? That the songwriter in question’s songs are difficult to neatly slot into a niche; that they are challenging; that they only reveal their full power to those who listen closely. All are true of Prine.

“He starts slow, but after a song or two, even the drunks in the room begin to listen to his lyrics. And then he has you.” —Roger Ebert, “Singing Mailman Who Delivers A Powerful Message In A Few Words,” Chicago Sun-Times, October 9, 1970

Although Prine has spent most of his career living and working under the radar (at least relative to his contemporaries), his lightning-quick ascendancy to success is the stuff of every aspiring musician’s idle daydreams.

In his own words, Prine was “such a good kid, childless couples used to borrow me.” He grew up in Maywood on the western outskirts of Chicago, part of a close-knit family with one foot still planted back in Western Kentucky, where his parents were born. Prine’s maternal grandfather played guitar with Merle Travis, an aptitude and appreciation that lived on in Prine’s father’s love of honkytonks and prodigious collection of country 78s and Prine’s older brother Dave’s accomplished fiddling (he appears on some of Prine’s earlier records and still sometimes joins Prine in the studio and on stage). Although as a teenager Prine learned to play “Twist and Shout” on the guitar to impress girls – and played for his buddies while stationed in Germany as a mechanic during the Vietnam War – he didn’t dip his toes into songwriting until he returned from the war and began working as a mailman, where his route gave him plenty of time to daydream and hop in the Relay Box to hide from the wind, eat a ham sandwich, and write.

The time he spent hiding in that Relay Box produced the songs on his debut album. All the while, he kept his work under wraps — not even his wife knew he was writing songs — though he did make a habit of hanging around Chicago institution Old Town School of Folk Music, taking lessons intermittently and playing with his classmates at nearby bars after class. At one of those bars — the Fifth Peg — Prine auditioned for a regular gig on a dare from a friend. At his audition, Prine played “Sam Stone,” “Hello In There,” and “Paradise”: three of the best songs he’s ever written; three songs most songwriters spend their whole careers trying to write. Unsurprisingly, Prine got the gig, which quickly turned into a Friday/Saturday night residency, which he supplemented with another regular gig at Earl of Old Town — a bar across the street from The Second City Theater.

Word got around. Bill Murray and John Belushi frequented Prine’s sets at Earl of Old Town and would later pester Saturday Night Live into giving Prine a musical guest spot. Roger Ebert, who did some music writing back in the 1970s, saw Prine perform, caught the spirit, and captured it in an effusive review. And Prine’s Fifth Peg residency brought him into songwriter Steve Goodman’s orbit at a fortuitous time: Goodman and Arlo Guthrie had recently scored a hit with “City of New Orleans” and the industry had Goodman’s ear. Once Goodman played some of Prine’s songs for Kris Kristofferson, Kristofferson asked Prine to open for him. Atlantic Records A&R man Jerry Wexler saw Prine open for Kristofferson, and the next morning, Prine had a record contract with Atlantic — less than two years after getting onstage for the very first time.

Prine’s distinctive perspective and hard-to-categorize style helped put him on the fast track to success — but also became his biggest barrier to achieving widespread fame. It’s rare to be a singular voice, and it’s hard to be universally loved if you are a singular voice, especially if you also lack virtuosic guitar skills, a penchant for self-promotion, and other flashy touches that draw fans in droves. But there was plenty to reward those who were listening.

A junkie veteran with the best intentions and worst outcome. A woman trapped in a distant and unfulfilling marriage. Two of the best songs ever written about lonely people — the way they relate to one another; the way they relate to the world. Prine’s curiosity, wisdom, and empathy give him the ability to go a mile deep on anything or anyone. He chronicles his characters’ indignities and triumphs in full and possesses the rare ability to weave his own memories into songs without making his songs about himself. “When I’m taking from a personal experience, I can’t always remember exactly what was happening, or how it came about,” Prine tells me over the phone earlier this year. “But I always remember the way I felt. And usually that works on the audience as well. They relate to it in their own way, they come up with their own story, and they feel like they’re a part of the song. I have no idea how I do that! I’m just gambling that the audience will get the same thing out of it that I got.”

It’s not something any gifted storyteller consciously does, but it’s something all good storytellers do: make the personal feel universal, and the universal feel personal. As a child, Prine witnessed the aftermath of a freak accident: a boy his own age hit and killed by a commuter train, which later became the opening verse of “Chain of Sorrow (Bruised Orange),” a spare description of an earth-shattering personal experience that gradually blossoms into a primer on how to live life on nodding terms with death without letting its nearness ruin your life. “The Great Compromise” cleverly personalizes the country’s widespread post-Vietnam disillusionment, casting America as a fickle date who leaves with someone else and an entire generation as America’s jilted lover. In “Sabu Visits The Twin Cities Alone,” Prine imagines the life of Sabu Dastagir, a real actor who attempted to reboot his career at 38, having starred as a teenager in a series of popular, problematic movies. Sabu tours the Midwest in winter, riding an elephant through shopping malls for the amusement of the public to promote films people stopped caring about long ago. In the song, Prine vividly captures resignation and humiliation, the steps you take when you’re no longer the one deciding where to put your feet—yet he treats his subject with dignity the whole way through. That matter of dignity, the willingness to be careful with a character’s story, the ability to write complicated characters living complicated lives without forcing a lesson or wrapping up their stories in a tidy bow: together, they are the reasons Prine’s songs feel real—and the reasons his songs are really affecting. He has never needed to preach at you because he knows if you tell a story honestly, listeners find the gospel on their own.

That honest, straightforward approach to songwriting is the perfect conduit for his brand of existentialism. In Prine’s songs—as in real life—the world doesn’t spare people or mourn their tragedies; their struggles are only meaningful because he makes them mean something to us. He grapples with death and violence like few other songwriters: directly and frankly, but with a droll, affable touch. His teenage Jesus cheekily compares his body during crucifixion to a wine cask getting pierced by a corkscrew; successive verses in “That’s The Way The World Goes Round” reminds you that life could trap you in a cycle of domestic violence, or the sun might do you a solid and free you from your frozen bathwater. Death and life, tragedy and redemption—in Prine’s songs, each gives the other meaning. Lake Marie is significant because it is a place that contains multitudes: its lapping shores are the site of two grisly murders but also the birthplace of a perfect memory—the smell of grilling Italian sausages and the sight of a beautiful woman, wind whipping through her hair.

Prine’s songs apply a whimsical filter to a fatalistic outlook: they depict life as relentless, but the people who populate Prine’s worlds seek and find the sublime in the mundane, the four-leaf-clover growing out of the pile of shit. They settle for Pretty Good lives, and relish the moments that make them the Pretty Good-est.

In my own conversation with Prine (and in almost every interview he gives) he talked about how hard it is to write, and how hard it is to get him, specifically, to write: that every song feels like his last song. “I don’t write as much as I used to, only because when I first started writing songs, it was my getaway from the world, you know? My escape. And now it’s my job,” he says. “Any time anything resembles a job to me, I run the other way. When I get into it, I remember how much I enjoy it. But whenever I’m not writing, it seems like a massive undertaking to go write a song. Almost like I’ve never done it before, you know?” It certainly explains the circumstances under which The Tree of Forgiveness, Prine’s first album of new material in 13 years, came into the world. “My wife is my manager now and my son is running [Oh Boy Records], and the two of them came to me last summer and said, ‘It’s time to make a record,’” he says. “They put me in a hotel suite downtown in Nashville. I took about ten boxes of unfinished lyrics down there with me—I looked like Howard Hughes checking in—and four guitars, and my suitcase. I just I holed up there for a week and wrote until I had ten songs I wanted to use for a record.”

For someone for whom songwriting has historically been a solo pursuit, in recent years Prine has become an artist who’s both eager to, and adept at, collaborating with other songwriters. “It took me a while to warm up to it, though,” he says, “When I moved down here to Nashville, everybody here collaborates. And I thought I can’t really do that—so what I do is, if I like somebody and they happen to be a songwriter and I’m hanging out with them, I sit down and co-write. But I can’t just make an appointment with a stranger.” To wit: all but five tracks on 2005’s Fair and Square are co-writes, and every song on Forgiveness represents some sort of creative collaboration, whether it’s Prine completing a song he started decades ago, Prine finishing “God Only Knows,” which he and Phil Spector started back in the 1970s, or Prine co-writing with long-time collaborator Keith Sykes, band member Pat McLaughlin and the Black Keys’ Dan Auerbach. Writing partners inevitably bring their own styles and perspectives to the creative process, but Forgiveness still draws from a familiar well: these are unmistakably John Prine songs. When I told him that, he laughed and said, “I’m glad I’m still able to sound like John Prine.”

Forgiveness doesn’t just sound like John Prine; it’s downright impossible to listen to the album without thinking about it from the perspective of John Prine, Age 71. These are songs about the passing of time: some revel in its ability to heal us (“Boundless Love,” written for his wife Fiona, “who saved my life”), some grapple with the understanding that it will inevitably steal what we love, whether it’s a relationship’s salad days (“No Ordinary Blue”), or Pluto’s planethood (“The Lonesome Friends of Science,” which according to Prine, “Comes out of a long-time rant that I had about taking away the title of Planet from Pluto. I thought, well, I can’t talk about Pluto for three verses. So I stole a verse from an unfinished song about the Vulcan statue in Birmingham and wrote a third. It all started to come together, especially with that nonsensical chorus about the world ending and ‘I don’t care because I don’t really live here.’ I thought, that’s a real John Prine song right there.”)

There are plenty of reflections on lives well lived, like the rollicking “Egg & Daughter Nite, Lincoln Nebraska, 1967 (Crazy Bone),” inspired by Prine’s fishing buddy’s cherished teenage memory of Thursday nights in the rural Midwest, when all the farmers in the region dropped their daughters off at the roller rink while they sold their eggs in town. And then there’s “When I Get to Heaven,” a wry but cheerful ditty about what you gain when you lose it all, from seeing your dearly departed family members to being able to enjoy a cocktail and a cigarette again. “I wrote this goofy thing about having my cocktail and a nine-mile long cigarette and then thought, ‘Where in the heck can I do that? Heaven!’” he says. “There couldn’t be any cancer in heaven, so I’ll be able to smoke again up there. That’s how the idea came about for the song. And I just started talking about all things I was going to do when I got to heaven and it all kind of worked out.”

Prine’s vision of heaven mirrors his experience on earth: spending some time misbehaving and running wild, checking into a swell hotel to write a great album, digging deep for forgiveness, seeking the comfort of loved ones. Just like the grim yet gentle great beyond in “He Was In Heaven Before He Died,” this afterlife is perfectly imperfect. It’s a place where it’s easy to do all the things you most want to do, whether it’s the good deeds you should have been doing all along, or the sort of things you probably shouldn’t ever do.

For Prine, in heaven as on earth, imperfection is perfection. He and his songs remind us we can’t appreciate the light unless we’ve seen the shadows.