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The Life of John Prine, the Mark Twain of American Songwriting

How the veteran artist took the folk scene by storm, wowed his hero Bob Dylan and beat cancer, all while inspiring today’s country stars.

John Prine sits behind the wheel of his Cadillac DeVille on a sunny Nashville afternoon, humming along to a cassette of Jerry Lee Lewis’ country hits. He slows down as he approaches a series of television-production trucks parked near his house. They’re probably here because his neighbour, country singer Kellie Pickler, is filming a reality show for CMT. Prine’s 21-year-old son, Tommy – home from college for the weekend and riding shotgun – says he’s gotten to know Pickler while out walking his dog. “Never met her,” Prine rasps. “All I know is she has three garbage cans and I have one.”

The singer’s presence, Prine adds, has invited “Homes of the Stars” tour vans to his neighbourhood, which stop outside his house twice a day. Tommy recently caught his dad spacing out as he stood near his mailbox – “bright-red sweatpants, gravy-stained T-shirt” – oblivious to the tourists taking photos of him. “God knows what they say about our place,” Prine says.

Prine, 70, has never been the kind of artist to draw much attention to himself. But in his own unassuming way, he’s built one of the most impressive catalogs of any songwriter of his generation. He emerged on the Chicago folk scene in the late Sixties, singing about the characters he encountered in the Midwest – heroin-addicted veterans, lonely housewives, the elderly – in songs that combined heavy realism and deceptive wit and often took surreal and unexpected turns. Bob Dylan’s favourite Prine song is “Lake Marie,” in which three radically different storylines – an Indian legend, a troubled couple on a camping trip and a brutal murder – converge at Prine’s childhood vacation spot. “Prine’s stuff is pure Proustian existentialism,” Dylan said in 2009. “Midwestern mind-trips to the nth degree.”

Today, Prine is giving his own version of a “Homes of the Stars” tour. “There’s Waylon’s old place,” Prine says, gesturing at a big Victorian brick house on Music Row. “Used to be outlaw central for a while.” He points out the house that once belonged to Cowboy Jack Clement, the former Sun Records house engineer who wrote several rock & roll classics, including Johnny Cash’s “Ballad of a Teenage Queen.” Cowboy, as Prine calls him, is the reason Prine came to Nashville. In 1977, after Prine’s contract with Atlantic Records expired, Cowboy invited him out here to make a rockabilly album. “Cowboy’s motto was, ‘If we’re not having fun, we’re in the wrong business,'” Prine says. Backed by Nashville’s best session players, they recorded in Cowboy’s attic six days a week, around the clock. “We were high as dogs and playing some really good stuff,” adds Prine. They had so much fun that they never finished the album, but Prine fell in love with Nashville anyway.

Prine lives a quieter life these days. Usually he wakes up late, eats lunch at one of his favorite greasy meat-and-threes, then maybe washes his car, shoots pool or takes a nap before browsing eBay for old cars late into the night. “I look busy for a living,” Prine deadpans. “I leave the house so it appears I did something. Fiona knows to never ask me what I did today. She knows it’s absolutely nothing.”

Fiona is Prine’s third wife; together with their son Jody, they run Prine’s independent record label, Oh Boy, out of a home they converted into an office. His live shows are a similarly do-it-yourself enterprise. Mitchell Drosin, Prine’s longtime road manager, books shows directly with promoters, and Prine drives himself between gigs. Overhead is low: Venues’ $3,000 catering options are turned down in favor of a $12 deli tray and a few six-packs.

prine3Prine in Canada, November 30th, 1973.

Lately, Prine’s audiences have been growing. His songs have become a key reference point for young Americana stars like Sturgill Simpson, Jason Isbell and Margo Price, all of whom open for Prine. “We hold him up as our Hank Williams,” says Todd Snider, who has released music on Oh Boy. “His music is like Huckleberry Finn. You get it, then you listen to it five years later and you really get it. And you listen to it five years later and you go, ‘I get it!’ And then 10 years later you go, ‘Now I get it.'”

At Boston’s John F. Kennedy Presidential Library this fall, Prine was honoured with PEN New England’s Song Lyrics of Literary Excellence Award, which had previously been given to Chuck Berry and Leonard Cohen. Simpson, Rosanne Cash and John Mellencamp showed up to pay tribute. “I can’t help but think about a couple of my high school English teachers that are rolling in their graves,” Prine said in his short acceptance speech. To capitalise on all the recent attention, Fiona convinced Prine to record For Better or Worse, a country covers album on which he sings with fans like Miranda Lambert, Kacey Musgraves and Amanda Shires. Prine says he’s received three book-deal offers in the past year alone. “We’ve heard from all the big publishers,” he says. “I think I’ll wait a little bit. Till I make my big comeback.”

Prine’s office feels like a clubhouse: There’s a pool table, black-and-white family photos, a pinball machine and Christmas lights all over. Prine loves Christmas; back when he was single, he kept a tree in his house year-round. It’s one in a long series of Prine’s endearingly eccentric qualities. He’ll also pack at least four bags of luggage for his weekend tours – everything from framed family photos to Heinz ketchup to Archie comic books. “I never gave up on Archie,” Prine tells me. “I started picking up Archie comics when I was in my thirties, and then I started subscribing to them. I like that they put your age on there: ‘To Johnny Prine, age 43.’ I like Jughead mainly. He had this persona that he was shifty and lazy, but he always kinda knew what was going on.”

“John’s mind don’t work like everybody else’s mind,” says Prine’s friend and engineer David “Fergie” Ferguson. “He really thinks outside the box, you know. And when he comes up with something, it might strike you as being really off-the-wall, but then after you think about it for a minute, it’s like, ‘OK, now it’s obvious.'”

In one corner of Prine’s office is a pristine 1942 Wurlitzer jukebox, stacked with old country 78s. It was a gift from his late friend and music partner Steve Goodman after they wrote “You Never Even Called Me by My Name,” a goofy satire of country music. “I thought it was a joke,” says Prine, explaining why he declined to list himself as a writer on the song. “Next thing I know, David Allan Coe does it, and it goes to Number One.” (The song actually went to Number Eight – Prine admits he tends to exaggerate.)

He likes the Wurlitzer because it reminds him of his dad. Bill Prine, a factory worker in Maywood, Illinois, a blue-collar suburb of Chicago, would take John and his brothers out to the honky-tonks and play the jukebox. “He was a big guy – six-two, 250 pounds,” Prine says. “He would more or less go into bars and announce that if anybody thought about doing anything like fighting, that they should get it over with, so he could have a good time.”

“I look busy for a living,” Prine deadpans. “I leave the house so it appears I did something. My wife knows to never ask me what I did today. She knows it’s absolutely nothing.”

Though the Prine family grew up in Maywood, Bill Prine drilled into the kids that they were also from somewhere else: Paradise, Kentucky, a small coal-mining town where Bill grew up before moving north to find work. “One time I went to school and they asked us all to find out where our roots were,” Prine says. “It’s goin’ around the class, and the kids were going, ‘I’m Swedish-German’ or ‘I’m English-Irish.’ They got to me and I said, ‘Pure Kentuckian.’ ” (In 1971, Prine would release “Paradise,” a song that became a country classic, covered by everyone from Roy Acuff to the Everly Brothers.)

The family spent its summers in Paradise, where bluegrass was big, leading John to study Doc Watson–style fingerpicking with his older brother, Dave. It wasn’t until John heard Dylan that he saw a future for himself as a songwriter. “By the time Bob Dylan and Johnny Cash hooked up [for Nashville Skyline], that’s when I thought, ‘Man, there’s something there where their two paths crossed. My stuff belongs right in the middle.'”

Before he could pursue songwriting, Prine was drafted into the Army in January 1966. He lucked out when he was sent to West Germany instead of Vietnam, working as a mechanical engineer, “drinking beer and pretending to fix trucks.” He often reminds himself that other draftees weren’t so fortunate: On his office table he spreads out a stack of small black-and-white photos of various boot-camp buddies who went to Vietnam and came home in a box. “Look how many of them are African-Americans,” he says. “And they tell me that that’s the lottery system?”

After coming back from Germany, Prine returned to his job as a mailman in Maywood. On his postal route, he worked out songs like “Your Flag Decal Won’t Get You Into Heaven Anymore” – a hilarious indictment of misguided patriotism – and “Sam Stone,” about a vet who gets hooked on morphine during his service and comes home a different person. The chorus: “There’s a hole in Daddy’s arm where all the money goes/Jesus Christ died for nothin’, I suppose.”

When Prine played “Sam Stone” at his first-ever performance, an open-mic night at Chicago’s Fifth Peg in 1969, he was greeted with icy silence. The “Jesus” line made many audiences angry. “They’d start to have an argument with me when I was onstage,” says Prine. (Johnny Cash had Prine rewrite the “Jesus” line when he covered “Sam Stone” in the Eighties, to “Daddy must have hurt a lot back then, I suppose.” “If it hadn’t have been Johnny Cash,” Prine says, “I would’ve said, ‘Are you nuts?'”)

Prine’s career took off fast: A couple of open-mic appearances got him a residency at the Fifth Peg, and then a $1,000-a-week regular gig at Earl of Old Town, the center of the Chicago folk scene. The club was across the street from the Second City theatre, and Bill Murray and John Belushi (who later helped Prine secure a slot as a musical guest during the second season of Saturday Night Live) frequented his sets. Roger Ebert, then a young Chicago Sun-Times staff writer, stopped by one night and wrote an article titled “Singing Mailman Who Delivers a Powerful Message in Few Words.” On another occasion, Steve Goodman brought Kris Kristofferson to the Earl. “By the end of the first line, we knew we were hearing something else,” Kristofferson recalled later. “It must’ve been like stumbling onto Dylan when he first busted onto the Village scene.” Kristofferson soon invited Prine onstage in front of an industry-heavy audience at New York’s Bitter End. The next morning, Atlantic Records president Jerry Wexler offered Prine a $25,000 contract. “This is my first night in New York, so it was like Oz to me,” Prine says.

Kristofferson would also introduce Prine to Dylan. One night Prine wound up at Carly Simon’s apartment, where Dylan – largely off the grid after his 1966 motorcycle accident – shocked Prine by singing along with several songs from Prine’s not-yet-released debut album. “The album wasn’t even out and he knew the words because he had an early copy,” Prine says. “I’m thinking, ‘This is like a dream.'”

Prine with Bonnie Raitt, 1993

Prine became a fixture of the Seventies folk scene, smoking and drinking beer while spinning yarns between songs. “He was incredibly endearing and witty,” says Bonnie Raitt, who would cover one of Prine’s most famous songs, “Angel From Montgomery,” in 1974. “The combination of being that tender and that wise and that astute mixed with his homespun sense of humor – it was probably the closest thing for those of us that didn’t get the blessing of seeing Mark Twain in person.”

Though his record sales slowed down, Prine’s writing grew more adventurous and profound. “Jesus the Missing Years” theorises what Christ might have done during the 18 years of his life unaccounted for in the Bible, while “Sabu Visits the Twin Cities Alone” uses the sad story of Sabu Dastagir – the Indian actor from 1937’s Elephant Boy – as a meditation on loneliness. “Who writes songs like that?” Mellencamp asked onstage at Prine’s PEN Award ceremony. “Two people come to mind: God and John Prine. … John taught me a lot, whether he knew it or not. He was a natural-born earthshaker. I know the record companies had no idea what to do with John Prine. ‘He’s not country, he’s not rock – what are we gonna do?’ And he said, ‘To hell with it. I’m gonna do what I’m gonna do.’ And he did.”

Prine calls the Eighties his “bachelor years.” “I was also married to my bass player in that time,” he clarifies, referring to his second marriage, which lasted from 1984 to 1988. “But I think our marriage was doomed from the get-go.” Back then, Prine would wake up around 3:30 in the afternoon and head to Brown’s Diner for fried eggs and his first beer of the day, then chat with fellow regulars Townes Van Zandt and Don Everly and play the poker machine. Brown’s didn’t serve liquor, so he’d go to Melrose Billiards (which he calls Chandler’s), one of many Nashville bars that still serve a Handsome Johnny – vodka and ginger ale. Then he’d hit the grocery store. “All my buddies knew that my dinner would be ready about one in the morning,” he says. “So when they were on their way home from the clubs, they’d all stop at my house and stay until about the time the sun came up.”

“He was on the night shift for a long time,” says Ferguson, who remembers sitting at Prine’s Fifties Formica table and playing Hank Williams and Merle Haggard records as friends like Van Zandt and Guy Clark dropped by to play cards. Cocaine and quaaludes were rampant. Prine wasn’t much of a weed guy: “If you smoke hash, it was kinda like buying a train ticket. You just run a straight train ride and you know what town you were getting off at. With some of the weed going around, you don’t know where you’re goin’.”

Today, Chandler’s is empty, apart from a smoking bartender and a few grizzled locals here to gamble on a horse race. One of them is Hooter, a friendly, pony-tailed character who worked for decades as the Everly Brothers’ tour manager. “Hooter was there in my wild years,” Prine says.

“I was totally involved in his wild years,” Hooter corroborates. Hooter shares a few stories, like the one about Prine’s tropical-fish tank. One night, while they were out barhopping, Prine’s heater shorted out and killed all of his fish. Prine was distraught. He had become attached to a goldfish that had grown to a pound and a half. After storing it in the freezer for months, Prine took the fish to a taxidermist and had it mounted, explaining it was the family’s favorite pet. “I said, ‘The kids miss it,’ ” says Prine, who had no children at the time.

Prine admits he was basically a child himself back then. All that changed when he met Fiona in 1988 at an after-party in Dublin, where she was working as a recording-studio business manager. They kept in touch for years before she left Ireland for Nashville in 1993. (The Prines still keep a summer home near Galway.) “There were a lot of things stacked against us,” Fiona says later. “He was on the road and had been through two marriages.”

“I was a high risk,” Prine says. At 48, Prine became a father for the first time when their son Jack was born. Tommy followed the next year, and Prine also adopted another son, Jody, from Fiona’s previous relationship. “It put my feet right on the ground,” he says. “I didn’t know that I was missing that until I found it. All of a sudden I felt normal with a capital N. I didn’t realize it, but it was something that I was striving for after years and years of being a total daydreamer.”

The honeymoon ended in 1996, when Prine visited a doctor about a lump on his neck. He’d been shaving around it for a while, thinking it was a blood vessel; it was actually stage-three neck cancer. Prine was dumbfounded. “I felt fine,” he says. “It doesn’t hit you until you pull up to the hospital and you see ‘cancer’ in big letters, and you’re the patient. Then it all kind of comes home.”

Surgeons removed the tumour, taking a chunk of Prine’s neck with it. The surgery left his head permanently slumped, which means he spends a lot of time staring at his shoes when he walks. It also makes him stick out in public – he’s used to getting stared at, especially by curious children. “I didn’t think there was any use in me wearing a turtleneck sweater,” he says.

In the wake of the surgery, he felt weak and his voice lost a lot of its power. He took a year and a half off before booking a small theater show in Bristol, Tennessee, as a test. He was nervous. “The crowd was with me. Boy, were they with me,” he says, his eyes tearing up. “And I think I shook everybody’s hand afterward. I knew right then and there that I could do it.”

“It sounds a little cliché, or Pollyannaish,” says Fiona. “But John and I don’t laugh at this: That neck is proof there is a God. That neck is the hand of God, because it gave him more than was taken away. Not to say it wasn’t hard. It was very hard for him.”

It could be hard for his kids, too. According to Fiona, Prine’s physical ailments made it difficult for him to keep up with the boys. They also struggled with the fact that he was on the road a lot. “He wasn’t a PTA dad, but he did what he could,” she says. But lately, their relationship has improved, especially with Jack starting to write songs and Tommy studying music management and hoping to work at Oh Boy. When Fiona recently asked Tommy how he felt about his father’s absence when he was younger, his response was definitive. “Mom,” he said, “my dad’s a freakin’ legend.”

Prine says there’s one downside to finding happiness late in life: His writing has slowed down. “The one thing I can’t remember about writing songs is just how fucking simple it is,” he says. The Black Keys’ Dan Auerbach, who’s been co-writing with Prine, says Prine can write when he wants to: “These phrases you’re looking for – they just pop out of his mouth,” Auerbach says. “Like it’s magic or something.”

This year, Prine is hoping to release his first album of new songs since 2005, but he’s finding it to be a torturous process. “I don’t wanna just sit down and write a little couplet that’s kind of witty, or something. I’ve done that,” he says. Occasionally, he stumbles upon an idea he can hang onto. At Chandler’s, we end up discussing religion. Prine believes in God, but he’s sick of the way evangelical Christians use the Bible as a political weapon against gays and transgender people. “I think of the Bible as an unauthorised biography,” says Prine. “I think that the disciples were all trying to vie for their personal time that they spent around Jesus. If I wrote anything, I would go toward that. I think I would make the center of it like, ‘Kitty Kelley Wrote the Bible.’ That’s a little marble that’s rolling around in my head right now. And that marble gets bigger every day.”

Prine with wife Fiona circa 1991

After a couple of beers at Chandler’s, we head to Prine’s house and sit on a porch overlooking his pool and Fiona’s large garden. Fiona comes by to ask if salmon is OK for dinner. Prine yawns – he’s not used to drinking beer during the day anymore, and it’s made him a little tired. “I can tell,” Fiona says.

At dinner, Prine sits at the head of the table, next to Tommy and his college friends, chiming in on matters from college hockey to whether Tommy should get his real-estate license. “Not a bad idea,” Prine says. “You’d make a killing in one summer. You just smile a lot. When the doorknob breaks, or the plumbing, you just go, ‘It’s very fixable.'” After dinner, Tommy and his friends make their escape, promising Fiona on their way out that they won’t be drinking. She’s skeptical. “Youth,” Prine grumbles when they leave.

He and Fiona look over a proof of a coffee-table book that includes guitar chords, lyrics and photos from throughout Prine’s life. She points out lyrics to various songs, like “Space Monkey” – written about one of the monkeys the Soviet Union sent into space in the Fifties – and 1972’s amiably apocalyptic “The Late John Garfield Blues.” “Your handwriting was a lot better then,” says Fiona. “I was a lot more together,” he replies. “You should’ve known me back then.”

Next is a picture from around the time of Prine’s 1978 album Bruised Orange. As part of the promotional campaign, three twentysomething girls in a record store dressed in big round costumes meant to look like oranges, though they ended up looking like pumpkins. “We invited them back to the hotel, actually,” Prine says. “And it turns out they were stuffed with old pages of Rolling Stone inside their costumes.”

“We won’t ask how you found that out,” Fiona says with an eye roll.

As I prepare to leave, Prine disappears and comes back with two more items to show off. One is a gift Jody got him for Christmas last year, a custom painting of Prine with the characters from Archie, titled “John Prine Plays Riverdale.” He looks at it and lets out a big, whooping laugh, despite having seen it countless times. The second is the mounted goldfish, which he displays outside, overlooking the pool. “I like hanging it somewhere prominent,” Prine says. “So people go, ‘What’s this?’ Then I get to tell the story.”

From issue #784 (March 2017), available now. Main photograph: Prine at home in Nashville. Credit: David McClister