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The Sweet Songs, And Sweeter Stories, Of 'John Prine'

On December 28, 2020

It’s the late ’60s and USPS worker John Prine, still carrying the glinty eyed, apple-cheeked remnants of boyhood on his face well into his early 20s, is seeking refuge from the gnarly Chicago winds along his daily mail delivery route. He crams himself into a relay box, those large, slotless olive green drop boxes for one carrier to leave mail in for later pickup by another. As he enjoys a ham sandwich and a moment of rest, he lets his mind wander, and writes the bulk of “Hello in There,” an eerily accurate song about the loneliness and resignation of old age, penned by a young man only a few years removed from adolescence.

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Despite his relative youth at the time, Prine constructs an unbelievably detailed and empathetic portrait of elderly existence — a population for which his affinity had grown while delivering papers to a Baptist old folks’ home, where lonely residents would often treat him with the familiarity and warmth of long-loved kin, instead of just a near-stranger delivering their mail. While the track would one day go on to be one of many of his most heralded songs, it’s hard to say if Prine imagines “Hello in There” being heard much further beyond the tinny walls of that relay box. Back then, he wrote songs for himself: to pass the time, to occupy his mind, and occasionally (and to varied outcomes) impress a pretty love interest.

Prine might’ve just been writing songs to stay out of trouble in his youth or as a vessel for daydreaming during his USPS shifts, but not even his own relative ambivalence toward sharing his craft could get in his way. Because when John Prine told a story, he could convey that which comprised birth, death, and every oddity in between in a warm light just as funny and sweet and twisted and devastating and filled with levity as the whole of life itself — regardless of who happened to be listening. But eventually, reluctant as he may have been, the world couldn’t help but pay attention.

True to form, Prine’s first performance happened unplanned, on a dare. It was a Sunday evening in 1970, and he was among the 20-or-so attendees at an open mic at a tiny, now-defunct Chicago club called Fifth Peg. While not usually the type to indulge in heckling, Prine was a few beers deep, unimpressed by the talent, and began kvetching under his breath. The folks nearby overheard him; if performing was so easy, they asked, why didn’t he just do it then? So he did. Nervous and unfamiliar with singing for anyone besides himself, his tone landed somewhere between talking and song, but neither nerves nor novice performance skills were a match for the arresting lyrics of a song like “Sam Stone.” Following his service in the Vietnam War, Prine penned his catalogue’s most forwardly heart-breaking song about a vet-turned-addict who dies of a heroin overdose, drawing inspiration from both a cohort of stories from his friends and fellow veterans, and a 1957 film noir called A Hatful of Rain. He later described getting on stage for the first time, uneasy that audiences wouldn’t like or understand his songs, so he was certainly unaware that “Sam Stone” — and the majority of his songbook for that matter — would go on to move and inspire generations of artists and songwriters throughout the course of time.

“‘Sam Stone’ is one of the most tragically beautiful songs ever written,” country singer Margo Price wrote to VMP. “I could never get through seeing John play it without pools of tears welling up in my eyes. I sat side-stage and watched, completely in awe and totally transfixed by the lyrics, thinking, ‘How was this one of the first songs John ever wrote?’ These are the kinds of sad stories that often slip through the cracks of humanity, but somehow John could paint it in a way that so perfectly made sense. The imagery will both break your heart and heal it — when a vein is a bottomless hole, heroin is a gold mine, the pain is a freight train, and the bad memories are a monkey on his back. Sam Stone was a war hero who deserved more than he got. All veterans do; they did then, and they still do now. He was damaged and used and died alone. At one point, he was probably a good man: a good father and husband. But existence was bleak and the baggage that war had left him with made him turn into something else: a martyr, a thief, a junkie, a dead-beat daddy who died alone. Sam is the broken radio and John is the sweet song that played for both a short while and forever.”

From the impromptu moment that 23-year-old John Prine began sharing his songs at Fifth Peg, opportunities began falling into his lap in droves. After playing “Sam Stone,” a couple other songs, and a nerve-wracking bout of silence from the crowd — followed by his first relief-inducing round of applause — the owner of Fifth Peg offered him a job on the spot. He barely knew what a gig was at that point, but all Prine had to do was play three 40-minute sets each Thursday, and he could keep half the door. Now tasked with time to fill, Prine’s catalogue continued to expand and refine. He was now regularly performing the songs that would turn up on his debut album to crowds of dozens at a time. Among the setlist of his first performances was “Paradise,” an old-as-time-sounding folk waltz that sounds like an aching homesickness for a place to which you can never return. His father, William Prine, was born and raised in Paradise, Kentucky, a gorgeous little town, and the site of many of John’s childhood memories, that was ravaged and rendered obsolete by strip-mining coal companies. In the song, Prine begs his dad to take him back, to which he replies, “Well, I'm sorry, my son, but you're too late in asking / Mister Peabody's coal train has hauled it away.”

This music is special. Its everyday Midwestern simplicity, rural Kentucky roots, a city-bred flair, shiny country, ragged folk, laughable humor, crushing darkness, an unlikely cast of characters old and young, and songwriting so masterful and human that it bridged every ragtag bit of it together like it was music we were all born to hear.

One night, by sheer chance, the renowned Chicago film critic Roger Ebert stepped out of the film he was supposed to be reviewing and into Fifth Peg. (Prine later said Ebert was looking for a beer because the movie popcorn was too salty.) Ebert was rarely one to write about music, but after hearing “Angel from Montgomery,” “Hello in There,” and a handful of other Prine originals, he forgot all about his film review, and Prine’s first-ever review was published on Friday, Oct. 9, 1970, in the Chicago Sun-Times. Ebert’s lede is a plot summary of “Your Flag Decal Won’t Get You Into Heaven Anymore,” a clever, bouncy diddy in which a patriotic citizen is reading Reader’s Digest in a smut shop when an adhesive American flag decal falls out, so he sticks it on his window. He loves that little flag so much that he begins to stick the decals everywhere. The song’s narrator sticks so many on his windshield that, one day, he drives off the road, dies, and is denied entry into heaven; the bouncer at the pearly gates of heaven tells him it’s too crowded from “your dirty little war.”

After Ebert’s review, Prine started to pack every seat in the house, new gigs started rolling in, and he was able to quit his mailman grind, making the same income playing shows three times per week and sleeping in all he wanted. In fact, Prine was sleeping in the booth when his record deal came a-knocking. As he became more ensnared in Chicago’s folk scene, he met fellow singer-songwriter Steve Goodman, and they became instant friends. Goodman, who had been diagnosed with leukemia a year earlier and knew that his time on earth was limited, had all the hustle and ambition easygoing Prine may have lacked, and then some. One night, after his show at long-gone Chicago saloon The Earl of Old Town, Prine was snoozing, waiting for his check, when Goodman called saying he was on his way with legendary songwriter Kris Kristofferson and singer Paul Anka, whom Goodman had persuaded to come give Prine a listen. To an audience of three, he sang a handful of his songs, including “Sam Stone,” “Paradise,” “Hello in There,” and another song that was in frequent rotation in Prine’s sets at that time, “Donald and Lydia,” probably the only song in existence about masturbation with the ability to shatter your heart at the wonder of human loneliness and longing.

Kristofferson and Anka were sold. Kistofferson asked for an encore of all the songs Prine had just played and anything else he had. “No way somebody this young can be writing so heavy,” Kristofferson said later on. “John Prine is so good, we may have to break his thumbs.” Luckily, instead of busting any of his digits, they encouraged him and Goodman to get to New York, record some demos, and try for a record deal. Anka paid for their plane ticket, and by early 1971, the singing mailman was signed to Atlantic, now sharing a label with Aretha Franklin, Crosby, Stills & Nash, Roberta Flack, and Led Zeppelin. John Prine was recorded at American Sound Studio in Memphis (except “Paradise,” which was recorded in New York), produced by the esteemed Arif Mardin, and released the same year.

“Things happened really fast,” Prine later marveled while discussing the whirlwind of his early career. It’s easy to say he got lucky, and he probably did, but in addition to that, his songs were, and remain, a rapid agent of intense connection. What Ebert and Anka and Kristofferson and Goodman — and everyone else along the way willing to break their necks to jump on Prine’s bandwagon — heard was something that only takes one listen of John Prine to understand: This music is special. Its everyday Midwestern simplicity, rural Kentucky roots, a city-bred flair, shiny country, ragged folk, laughable humor, crushing darkness, an unlikely cast of characters old and young, and songwriting so masterful and human that it bridged every ragtag bit of it together like it was music we were all born to hear. There wasn’t ever anyone like John Prine, and there probably never will be again, but boy, weren’t we lucky he happened to share this big, old goofy world with us in the first place?

Profile Picture of Amileah Sutliff
Amileah Sutliff

Amileah Sutliff is a New York-based writer, editor and creative producer and an editor of the book The Best Record Stores in the United States.

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