On a chilly October night around the north side of Chicago, Roger Ebert shuffled out of yet another lackluster movie screening in need of a drink. He drifted into a neighborhood called Old Town, which—in 1970—felt like a Midwestern Greenwich Village, replete with bookstores and cafes, hippies and folkies, sidewalk activists, and even a go-go bar or two. Ebert checked out a hole-in-the-wall folk club, the Fifth Peg, where an unassuming twenty-something from Maywood, Illinois was singing a few songs he’d written. “This was John Prine,” Ebert would recall years later, and, “out of sheer blind luck,” America’s favorite film critic discovered a national treasure.

A few days after the show Ebert wrote a glowing review—“Singing Mailman Who Delivers a Powerful Message in a Few Words”—that appeared in the Chicago Sun-Times on Friday, October 9th, 1970, a day before John Prine’s 24th birthday. It was the first review Prine ever received, a birthday gift in the papers.  For Ebert, Prine was “sneaky good”: “He appears on stage with such modesty he almost seems to be backing into the spotlight. He sings rather quietly, and his guitar work is good, but he doesn't show off. 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.”  The crowds kept coming back to hear Prine, who signed on to play every Friday, Saturday and Sunday, striking a chord somewhere between country, rock, and folk that sounded pretty good to most. The regulars at the Fifth Peg were doing sing-alongs before he had a record out. Why all the fuss about this “singing mailman?”

John Prine, who still tours today at seventy, has always emitted a warm, genuine modesty: not a self-satisfied, calculated humility, but an authentic, no-really-I’m-a-regular-guy manner of attraction. He once confessed of his time in the bars and clubs around Old Town, Chicago: “I was just floored that people paid me to sing.” The people, in turn, adored Prine’s music, especially his lyrics, which ring out like stories from a down-home friend: funny as hell, then a little too familiar, then downright tragic—strange and intimate and indispensable.

Prine, who “slept all week” and played the weekend nights, quickly made a few friends on the Chicago circuit, namely Steve Goodman, who couldn’t withhold mention of his buddy John: “Man, if you like my songs, you’ve gotta hear John Prine.” Kris Kristofferson, a burgeoning songwriter in his own right who spun a dark, brooding brand of Outlaw country and, more importantly, was friends with Johnny Cash, received the word from Steve Goodman—“I’m telling you man, John is good”—and showed up at one of Prine’s shows. “John Prine is so good, we may just have to break his thumbs!” was the verdict; Kristofferson booked Prine a flight to New York City, and, less than a year after hopping on stage at the Fifth Peg on a half-drunk whim, Prine signed a deal with Atlantic Records.

In interviews, Prine often thinks back on his mail-route with nostalgic disdain: he didn’t enjoy the job (“It’s a good job for somebody that doesn’t know what they want to do”), so he wrote songs to pass the time. Listening to this first batch of songs, which play like door-to-door vignettes, it isn't surprising that they emerged from a USPS company vehicle: utterly simple in their construction (“I’ve been playing the same three damn chords for 30 years,” Prine regularly tells concert-goers), vaguely anti-authoritarian (but not quite preachy), and eager to expose the unseen domestic dramas unfolding behind closed doors, behind lace curtains and wooden surfaces.

Prine’s eponymous first album, cut in a New York City studio with producer Arif Mardin, is stuffed with colloquial insight into the heart and heartland of an increasingly neurotic, fuzzed-out America; there’s a song about smoking dope (or dropping something else) (“Illegal Smile”), songs that wrestle with Vietnam veterans and warhawks but not the Vietnam war (“Sam Stone,” “Your Flag Decal Won’t Get You Into Heaven Anymore”), and even a strange, comic commentary on long-distance masturbation in the pre-sexting era (“Donald and Lydia”). Against these evocations of confused baby-boomers Prine spins stories about lonely old timers, forgotten seniors in worn-down homes, channeling what rock critic Robert Christgau called a “cross-generational empathy.” “Hello in There,” an early, easy G/C/D tune, belies its simple melody with a painful ode to a plaintive retiree and his wife Loretta, who sit around with “nothing much to do;” the last verse serves as a soft injunction to the non-arthritic: “So if you’re walking down the street sometime and spot some hollow ancient eyes, please don’t just pass ‘em by and stare as if you didn't care, say, ‘Hello in there, hello’.” This anti-elegy, a beseeching reminder to call your parents while you still can, is matched on side two by “Angel from Montgomery,” which finds Prine assuming the voice of a neglected housewife. “I am an old woman named after my mother, my old man is another child that’s grown old,” Prine intones. Again, as in so many of Prine’s subdued tales, there is a simmering aggression, delivered with a wistful smile that you can almost hear: “How the hell can a person go to work in the morning and come home in the evening and have nothing to say.” These songs hit hard, and, in the liner notes to the album, Kristofferson gets it right: “Twenty-four years old and he writes like he’s about two-hundred and twenty.” Prine’s first album was a critical success, if not a commercial one, and it attracted comparison to another singer-songwriter from the Midwest who, at the time, was idling in Greenwich Village: Bob Dylan.

John Prine enjoyed and recoiled from the coveted, dreaded “New Dylan” label. The inherited title, of course, was a company man’s dream; it boosted record sales and propelled Prine from bars and clubs to concert halls and festivals. And the comparison was not without merit: first-time listeners of Prine often mistake him for Dylan; the songwriters’ voices cover a limited range with a similar ease of delivery, an affected twang and drawl; both thrive off a peculiar, filial relation to country, folk, rhythm and blues; they emerged from the same roots, listening to the same records a few hundred miles apart. John Prine, along with everyone else, admired Dylan’s supreme craftsmanship, even modeling some of his first songs after what he heard on early Dylan records like “The Times They Are a’Changin’” and “Bringing It All Back Home.” What’s perhaps more surprising, however, is that Dylan, almost immediately, revered and interiorized Prine’s lyrics. In his impressive contribution to Dylan-ology, The Bob Dylan Encyclopedia, Michael Gray tells of an unplanned intersection of the two artists: “Prine was playing a solo gig at the Bitter End in the Village that September 9th and Dylan came quietly on stage, unannounced—and from Prine’s point of view, somewhat disconcertingly, perhaps—and played harmonica and sang back-up vocals on three numbers.” Dylan, it seemed, had obtained a copy of Prine’s debut album, and he, like the folks back in Old Town, knew all the words. In a 2009 interview with the Huffington Post, Dylan gushed about Prine’s abilities: “Prine's stuff is pure Proustian existentialism. Midwestern mindtrips to the nth degree. And he writes beautiful songs.” High praise from Dylan, who Prine once characterized as his biggest influence. Despite the mutual acclamations and familiar ground, in spite of the friendly (but limited) engagement between the two men, it must be said that Dylan and Prine are separate species. Where Dylan tended to defer meaning towards abstraction, Prine engaged with the concrete and neglected; when Dylan veered off into self-parody and pastiche, Prine held the line with a series of honest albums aimed at the heart, not the ironic intellect; when Dylan played the chameleon, Prine abided. Much has been made of the “Dylanesque,” but there’s a “Prineian” universe with flourishes and contours every bit as stimulating.       

John Prine often feels like a friendly neighbor, a buddy next door who occasionally comes over after work, pulls up a chair on the front porch, cracks open a beer, and tells you all about Roger down the street, chuckling through every sentence. Then, after he’s had a few, you notice a change: what was funny before now seems pretty bizarre; a few uncomfortable truths have entered the conversation, and you can only nod your head in tacit agreement; he’s still grinning—and you are too—but things seem much bigger than what Roger did last week. Prine is a deceptive lyricist and an elusive character; he revitalizes worn clichés with new meaning, and it isn’t clear if he’s “country come to town” or “town come to country”: is he a country boy in the big city or an urban folkie?

Prine grew up in a suburb of Chicago, but, as he warmly remembers on “Paradise,” his family often travelled “down to Western Kentucky where my parents were born.” Not unlike his musical influences, Prine’s personal history represents a convergence of Northern skepticism, Midwestern drudgery, and Southern insouciance: early in his career, Prine “slept all week” and, on the weekends, he sang sympathetic songs about retired workers. On “Spanish Pipedream,” a strange sort of travelogue with an ethical bent (Christgau called it “heartland hippieism”), Prine drifts from middle America into his own imagination, recalling what a “level-headed dancer” told him “on the road to alcohol”: “Blow up your TV, throw away your paper. Go to the country, build you a home. Plant a little garden, eat a lot of peaches. Try and find Jesus on your own.”

Prine is clearly a man apart, living through and breathing in middle class malaise, eager to escape without leaving the party, resolute on sitting by your side. If you ask him how he’s doing, he’ll answer honestly, as on “Pretty Good”: “Pretty good, not bad, I can’t complain, but actually everything is just about the same.” There is a persistent stoicism in Prine’s words, an acknowledgement that the world is broken but to wallow in the bad times is to admit defeat. Prine once described his music as “optimistic pessimism;” when times are tough, the bass line keeps chugging along, and there’s a joke around the corner. He isn’t much for complaining—“You got news for me, I got nothing for you. Don’t pin your blues on me, just go ahead and do whatever you wish to (“Quiet Man”)—so his response to the woes of the world often comes in the form of a home-cooked surrealism.

“Nobody but Prine could write like that,” Dylan said of the “singing mailman,” an appellation that now seems lacking. It takes a special mailman to deliver some of the outlandish scenes that surface in Prine’s songs. “That’s the Way that the World Goes ‘Round” encapsulates Prine’s ethos—“That’s the way that the world goes round, you’re up one day and the next you’re down. It’s half an inch of water and you think you’re gonna drown”—and features a perplexing bathroom fantasy:

I was sitting in the bathtub counting my toes,

when the radiator broke, water all froze.

I got stuck in the ice without my clothes,

naked as the eyes of a clown.

I was crying ice cubes hoping I'd croak,

when the sun come through the window, the ice all broke.

I stood up and laughed thought it was a joke

That's the way that the world goes 'round.

The journey from an arresting melancholia to a liberating, good-humored acceptance of life’s ups-and-downs is pure Prine. He has a nifty manner of dressing up familiar images in fantastic clothes. There’s the “bowl of oatmeal” that tried to stare him down “and won” (“Illegal Smile”), the speaking “knick-knack shelf” of “Six O’Clock News,” the heretical, teenage Jesus Christ who “cut his hair” and “rented a flat on the lower east side of Rome” (“The Missing Years”). Prine’s signature move is to make the listener comfortable—playing “the same three damn chords” will do that—and then surprise with an unexpected joke, a punch to the gut (“There’s a hole in daddy’s arm where all the money goes”), or a hallucinatory detail. He’s an absurdist in blue jeans.

Despite a vocal crowd of artists and songwriters who have called Prine an influence and a singular talent (including: Johnny Cash, Bruce Springsteen, Roger Waters, and, of course, Bob Dylan), most people will shrug at the name John Prine—“Never heard of him.” Prine has never had a hit album, or even a widely-recognizable song to hang his hat on; his fame is largely limited to fellow musicians, baby-boomers, and college kids whose fathers insisted on playing Prine on road trips. Randy Newman, also a master of comic songwriting (though in a dimmer, more sinister register), once commented on the two artists’ mutual lack of general-public popularity: “It’s a little odd, but I’m certainly not alone,” Newman said of his poor record sales. “There are people like John Prine, who gets way less recognition than he should.” Indeed, it seems that everyone who discusses Prine mentions how strange it is that more people aren’t familiar with his music. Prine isn’t obscure by any standard, but it’s surprising that a “New Dylan”—other “New Dylans” include: Bruce Springsteen, Patti Smith, Donovan, Paul Simon, James Taylor, Don McLean—is so far removed from public consciousness.

It’s difficult to venture reasons for Prine’s relative obscurity. There is a common trope in music magazines and barstool conversation that consists of an unwavering, neurotic attention to “an artist’s evolution,” a musician’s growth from album-to-album. It’s a specious way of looking at music, but, if we accept the idea for a moment, it might be argued that Prine has been guilty of creative stagnancy: his core albums—“John Prine,” “Diamonds in the Rough,” “Sweet Revenge,” and “Bruised Orange”—sound awfully similar, featuring those “same three damn chords” in the same verse/chorus/verse/chorus/verse arrangement. Prine himself would admit that he’s not an especially skilled guitarist—he often makes (very forgivable, always slight) mistakes in concert—so it isn’t surprising that his albums adhere to a comfortable formula. Ultimately, Prine’s resistance to musical evolution, which may have contributed to his lack of commercial success, boils down to a simple truth about his character as an artist: he’s never been interested in crafting an alternate version of himself, in establishing a showbiz persona. He has a cult following, but there is no “cult of Prine.” Dylan liked to mystify and hide behind a series of creative facades; Bruce Springsteen became “The Boss;” Paul Simon re-invented himself on “Graceland” (at the expense of Ladysmith Black Mambazo). Prine, on the other hand, has never been more than himself: he writes songs and people enjoy them and—after a couple of (long overdue) Grammy’s, an induction into the Nashville Songwriters Hall of Fame, and admirable recognition from peers and folk acolytes—it is now clear that his influence on popular music stems not from a cult of celebrity, but from a consistent slew of clever little songs that hit home.

In 1985, Bobby Bare interviewed John Prine on Bobby Bare and Friends, a relaxed program that featured Bare sitting down to chat with folk and country musicians. The interview is a window to the middle of Prine’s career:  fourteen years after his first gig at the Fifth Peg, Prine is more comfortable talking about the stories behind his songs than pitching his new album. But with a nervous confidence and a cigarette that just-couldn’t-wait in his hand, Prine tells Bare about his brand new record label, “Oh Boy Records,” founded by Prine himself:

"There ain’t no middleman, there isn’t no swarthy little character in Cleveland that gets the money from the people that want the music, and then he takes most of it and twirls his mustache and sends me twelve cents, ya know? So, I’m giving the records right to the people, and they give me the money, and, if I can save enough money, I’ll make another record, or I might just buy a little red boat and send them pictures of me."

Prine shifts in his chair a bit, and then he chuckles, maybe at the image of himself in that little red boat. In any case, he saved enough money to make quite a few more records and temper the tides of time.

A few years ago Prine appeared on another television program, this one more familiar: The Colbert Report. After forty years in the business, he’s still wearing a knowing grin, still telling strange jokes that take a moment to digest. Colbert plays his part in the interview, and Prine responds with characteristic wit:

Colbert: I got a beef with you, John Prine. I’m an enormous fan, as I said, but you like to keep it simple: it’s mostly just vocals and guitar. Why not flash pots, why not face paint, why not someone twerking against you while you’re doing your songs?

Prine chuckles, takes a moment to think, and then replies as if it were obvious: “Well, that would put me in a different tax bracket…” The audience laughs, and Colbert laughs along.  Later in the program, Prine plays a fan favorite, “Paradise,” with Colbert joining in on vocals. After all the years—after his older brother Dave taught him to play rhythm guitar, after the mail-route and a couple years in the Army, after Old Town and Greenwich Village and the Twin Cities, after a bout of cancer that should’ve ended his career but didn’t—John Prine is on national television with Stephen Colbert singing about his childhood in Muhlenberg County, Kentucky. Prine said it best: “It’s a big old goofy world.”