John Prine: The Last Days and Beautiful Life of an American Original

’s 50-year career had taken him from the folk clubs of Chicago to sold-out venues in London, Australia, and beyond. But as he planned the schedule for the final leg of his Tree of Forgiveness tour, there was still one place he needed to play: Paris.

The city had never seemed to care for Prine. His down-to-earth folk songs had spread to Ireland, England, and even Scandina. But a promoter told his touring manager Mitchell Drosin that there was no point in booking his first-ever show in France; Prine would lose money if he brought his band. “John said, ‘You don’t understand. I want to play Paris, and I want to stay at the George V,’ which is one of the most expensive hotels in the world,” says Drosin. “It’s a Four Seasons, it’s insane. I said, ‘You know, your hotel is more than you’re going to get paid. It’s just going to be a club show. John said, ‘That’s great.’”

Drosin booked a show at Paris’ 500-capacity Café de La Danse, much smaller than the other venues on the tour. Prine loved Paris in ways that even Fiona, his wife and manager, struggled to explain. “He always loved that Parisians] treated him with disdain, you know?” she says. “He just loved the people and the food and the idea he couldn’t understand a word they were saying. He didn’t have much of an ego.”

At the show, on February 13th, Prine was in serious pain from what he later learned was a collapsed hip. He was forced to sit in a chair onstage, something he never did. But he delivered, blasting through one of the most distinct catalogs in American popular music. There was 1971’s “Six O’Clock News,” the stunning story of a man who learns his family history was a lie and kills himself; “Angel From Montgomery,” his classic about the sadness of a suburban 1950s housewife; and 2018’s “Summer’s End,” a ballad he had dedicated to people suffering from America’s opioid crisis.

Prine invited Fiona and some visiting family members onstage to sing along to “Paradise,” a 1971 song about the devastation of the Kentucky coal-mining town where his parents met; in recent years, it had become an environmental anthem. Prine joked about his immobility, saying, “OK, now we’re coming to the encore,” because he couldn’t easily leave the stage. Prine’s sound engineer Andy Primus says Prine was “giddy,” telling more stories than usual: “People were sitting on the stairs and hanging over the railings, it felt like he was playing in your living room. Prine was feeding off the vibe and just having a blast.”

“He might as well have danced off the stage,” says Fiona. “He was so proud that he did that show, and it was sold out and they loved him. It felt like a victory lap.”

The entire tour had felt like a victory lap, in fact. Prine’s most recent album, 2018’s The Tree of Forgiveness, was his first LP of new material in 13 years, proving that even in his seventies he could write just as deeply as ever. For a half-century, Prine had covered subjects few others touched — the loneliness of the elderly, serial murders, a monkey lost in space — in songs that mixed deceptive simplicity with sharp storytelling and a touch of the surreal. Artists like Bob Dylan and Bonnie Raitt had long been huge fans. But in the 2010s, Prine had become something of a national treasure. His songs had become a key reference point for a new generation of songwriters. Dan Auerbach, Jason Isbell, and Amanda Shires lost money on the road so that they could open for him. Kacey Musgraves wrote a song where she fantasized about smoking a joint with him. Prine won lifetime achievement awards from the Grammys and the Americana Music Association. (“I’m getting Americana lifetime achievement awards, and I never knew what Americana was,” he said. “But let ’em call me what they want, as long as they call me.”) He was excited to keep it going. By the time he went to Europe this year, he had written a half-dozen songs for his next album and started work on an autobiography.

After the Paris show, Prine celebrated with a French cheese platter (he usually opted for $12 deli trays). His hip pain was so bad that he decided to cancel the rest of the tour, but before returning home, he and Fiona hung out in Paris for a few more days. They ordered room service every day, drank expensive wine, and watched movies like Joker. “I went out shopping on the last day we were there, and I bought him a whole bunch of gifts,” she says. “I just wanted to buy him gifts, because he always bought me gifts and he couldn’t go shopping because he couldn’t walk so well. I bought him a new ring that I’m wearing now. I bought him glasses. I just felt really tender towards him.” Prine had had a series of health problems, dating back to the cancer he beat in the late Nineties. “Part of me knew that maybe I wasn’t going to have a whole lot of time left,” Fiona says. “But I believed we’d have a couple of more years.”

Prine and Fiona flew home to Nashville, where Prine had successful emergency hip surgery. But in the days that followed, he developed a cough, which he assumed was related to his COPD. Since he’d been traveling overseas, a doctor tested him for COVID-19. As Fiona was walking out the door, the doctor suggested she get tested too. A couple of days later, they stood in their home, the doctor on speakerphone, listening to the results. John’s result was “indeterminate”; Fiona’s was positive. “I literally almost fainted,” she says.

She self-quarantined, leaving the house for a few days to stay somewhere else. While her case was mild, “it was like nothing I’d ever had before,” she says. “I would not compare it to the flu or a cold.”

At first, Prine seemed to be doing OK. He kept up with his physical-therapy exercises and stayed glued to the news; he had a habit of taping and watching all three network broadcasts each night. “He felt sorry for America,” says Fiona. “That it had come to this: that the political distancing was now a physical distancing. He would tell me about how when he was a kid, nobody cared whether you were a Democrat or a Republican. It was the last thing you thought about when you were at school or you were with your friends. It broke his heart that his country became this divided.”

Fiona returned home after getting cleared by the health department. She and John needed to stay separated, so she would talk to him from the top of the stairs. “He would tell me, ‘Yeah, I’m doing fine,’” she says. “Then one day when I asked him how he was doing, he said, ‘I’m just exhausted. I can’t stay awake.’”

The day she was cleared to stop quarantining, Fiona took Prine straight to the Vanderbilt University Medical Center, where his condition worsened. Two days after arriving, he was put on a ventilator. Because Fiona had had coronavirus and was likely immune, doctors allowed her to sit with John in the ICU. “I talked to him for 14, 15 hours a day and played music, played him other people doing his songs, played messages from all the kids and from his brothers and my family,” she says. “I told him things that I wanted to tell him. He couldn’t communicate with me, but I just assumed that he could hear me.” 

On April 7th, Prine died due to complications from the virus. He was 73. The outpouring of love and grief around the world was huge and effusive. His songs were streamed 20 million times in two days. Bob Dylan said, “John’s talent and sprit was a gift to the world. We were lucky to have seen and heard him.” Michael D. Higgins, the president of Ireland, where Fiona grew up, called Prine “a voice of tolerance, inclusion, whimsy, and protest, capturing] the experience of those on the margins in societies.”

“John and I were ‘New Dylans’ together in the early Seventies,” said . “He was never anything but the loveliest guy in the world. He wrote music of towering compassion with an almost unheard-of precision and creativity when it came to observing the fine details of ordinary lives. He was a writer of great humor, funny, with wry sensitivity. It has marked him as a complete original.”

In interviews, Prine gave the impression that his success was pure luck — bringing it all back to the moment when Paul Anka and Kris Kristofferson walked into an empty Chicago club in 1971 and saw him play, which led quickly to a record deal. But deep down, Fiona says, “He knew that all his songs were good songs, because they came from a place of sincerity. You know, divinely inspired. He had no doubt that he had a gift. And he respected it — even though he spent so many years, and so much of his career in the shadows.”

That gift goes back to when he was a kid in the Chicago suburb of Maywood, Illinois, in the early Fifties. “I always had a vivid imagination,” he told me in 2016. “It was the only thing I really shined at in school.” He remembered an English-class assignment. “The lesson was to write something completely from dialogue,” he said. “I wrote about an escalator and people going up and down and talking about stuff. And I got an A on that. It was the only thing that came easy to me.”

John looked up to his father, Bill, a tool and die maker at the American Can Company, an ardent Roosevelt Democrat, and president of the local steelworkers union. Though they lived in Maywood, Bill considered the family’s true home Muhlenberg County, Kentucky. He and his wife, Verna, grew up in the coal-mining region before moving north so Bill could find work. Every summer, the Prine family would drive there for huge family reunions. “That town was so magical to us, you know, because it was just way behind the times,” John said. It’s where he first heard bluegrass music; the region gave birth to Bill and Charlie Monroe and the Everly Brothers: “I had the opportunity to learn bluegrass music and these old country ballads. Maybe that’s what formed me.” When his parents’ hometown was strip-mined, Prine wrote “Paradise” about it.

Prine said his grades were “too ugly” for college. After graduating high school in 1964, he took the advice of his oldest brother, Dave, and became a mailman. The pay was good, and so were the benefits. That life was upended when Prine was drafted into the Army in late 1966, just as the Vietnam War was heating up. But instead of being sent to Vietnam, he ended up in Stuttgart, West Germany, where he worked as a mechanical engineer. Prine played down his military service, describing his contribution as “drinking beer and pretending to fix trucks.”

After the war, Prine returned to his mail route, which, it turned out, was great for writing songs. Wandering the Chicago suburbs, he wrote classics like “Donald and Lydia,” about a couple who “made love from 10 miles away,” and “Far From Me,” a ballad about the chilly, purgatory-like feeling that consumed him before his first breakup. “A lot of stuff I was writing about were things I saw and felt and didn’t hear them in songs,” he said. “It was about certain silent things that people didn’t talk about.” Prine’s most fearless song looked back on his Army days: “Sam Stone,” about a vet who came home from Vietnam and ends up with a heroin habit. “I was trying to say something about our soldiers who’d go over to Vietnam, killing people and not knowing why you were there,” Prine told Rolling Stone in 2018. “And then a lot of soldiers came home and got hooked on drugs and never could get off of it.”

Prine became an immediate sensation on the Chicago folk scene. Two days before his 24th birthday, he was performing at Chicago’s Fifth Peg when the Chicago Sun-Times critic Roger Ebert walked in. Ebert’s headline, “Singing Mailman Delivers a Powerful Message in a Few Words,” led to sold-out rooms. Soon after that, singer Steve Goodman brought the unlikely duo of Kris Kristofferson and Paul Anka to see Prine play at Chicago’s Earl of Old Town. Kristofferson would compare it to “stumbling onto Dylan when he first busted onto the Village scene.”

Kristofferson invited Prine onstage at New York’s Bitter End. The next day, Atlantic Records President Jerry Wexler offered Prine a $25,000 deal with the label. “It was like a Cinderella sort of thing,” Prine said. With Anka serving as his manager, Prine cut the majority of his self-titled album at American Sound in Memphis, with the studio’s house band, the Memphis Boys, famed for their work with Elvis Presley, Dusty Springfield, and others. (Prine was nervous: “As soon as I finished the last note of every song, I wanted to run out the door.”) The album barely dented the charts, but it quickly became a touchstone for everyone from Bonnie Raitt to Steve Earle.

Raitt remembers first hearing “Angel From Montgomery,” about a married  woman who felt old before her time. “The fact this very young man could inhabit this middle-aged woman,” she says, “and make it so real and so cinematic, it just touched me so deeply.” Raitt recorded the song in 1974, and it became one of her biggest hits. “I know ‘I Can’t Make You Love Me’ has the Grammy wins and all that,” she says, “ but ‘Angel From Montgomery’ will be the song that means the most to me and my fans, I think.”

Raitt and Prine toured a lot together, playing the college circuit. “I never ceased to be awestruck watching him perform — his mix of pathos and humor and sardonic wit, and his unique eye on the way people were,” she says. “I was just knocked out. He really was the same person onstage as he was offstage.”

Raitt remembers a lot of great times on the road, wandering new cities, partying all night in hotels. “I can’t even imagine my twenties without him,” she says. “I liken it to being Becky with Tom Sawyer and Huck Finn or something. We were immediately like young kids riding around on our bikes before your parents call you in after dinner to go to bed. The childlike excitement, and thrill of being with each other, and the playfulness, is what I remember the most.”

By the mid-Seventies, Prine had grown tired of trying to have a hit, and asked Atlantic Records to let him out of his contract. He visited Nashville in 1977, to make a rockabilly album with Sun Records legend Cowboy Jack Clement. “Cowboy’s motto was, ‘If we’re not having fun, we’re in the wrong business,’” Prine said. “We were high as dogs and playing some really good stuff.” They had so much fun that they never actually finished the album, but Prine fell in love with Nashville and the songwriters and studio musicians who worked behind the scenes there.

Prine moved to the city soon after, and his house became a popular stop for Nashville musicians after they were done playing the bars. “Back in the day, John would pull a turkey out of the oven between 12:30 and one in the morning with all the fixings — mashed potatoes and all the gravy,” his co-writer and former guitarist Pat McLaughlin said last year. “Not a lot of green vegetables because he didn’t care about green vegetables. He’d just kill time around Nashville, but he was always working.”

In 1981, Prine decided to start his own label, Oh Boy Records, with his manager Al Bunetta. They sold his 1984 album, Aimless Love, mail-order, with fans sending in checks. “He created the job I have,” said Americana songwriter , who released his early albums on Oh Boy. “Especially when he went to his own label, and started doing it with his own family and team. Before him, there was nothing for someone like Jason Isbell to aspire to, besides maybe Springsteen.”

Oh Boy Records was so successful that Sony offered to buy it for a hefty sum, but Prine turned them down. He’d grown comfortable with his obscurity: “And my music, because it wasn’t pop music, it didn’t get old,” he said. “It’s not like I had one hit or two hits and they froze me in time. So, by being kind of obscure during the years, it’s helped me in a way. People thought I was their private family thing. They’d play me on car trips, and the kids, they’d learn my songs and they’d sing along in the car. It’s kind of like the way that original folk music was learned and passed on.”

Fiona Whelan grew up in Donegal, in northwest Ireland. In 1988, she was 27 and working at a recording studio in Dublin when several American artists — the Everly Brothers, Cowboy Jack Clement, and more — came to town to open up a new venue. One of them was Prine. “I was really mesmerized by him, watching him onstage,” Fiona says. At the afterparty, she was hanging out at the bar with an old high school friend when Prine appeared next to them. Fiona’s friend introduced them, and Fiona asked if he would be coming back to play Dublin again anytime soon. “Actually,” he said, extending his arm out, “I’m thinking about singing right now. Do you want to come hear?” They spent the whole night talking, and he asked her to lunch the next day. “I was at my desk and a gal called up from downstairs] and said, ‘There’s someone here to see you for lunch.’ I said, ‘Who?’ She said, ‘It’s John Prine.’ I was like, ‘Wow, he showed up.’”

“He was cute, and he was kind of sexy,” Fiona says. “There was a little bit of danger about him, but he was gentle. That was one of my first impressions of John, was how gentle he was as a man. I was pretty tender-hearted. I’d lost my father, and it changed everything in my life. I’d had a son and had my own home. I was working and I was just getting on with my life, but I was lonely.”

Fiona and her son Jody soon moved to Nashville. At 48, Prine had been married twice. “I was a high risk,” he said. But he jumped into family life. Fiona gave birth to their son, Jack, in 1994, and Tommy the following year. Jody was about 12 when he came to America, and he quickly had to learn to adjust to life with a songwriting legend as his father figure. “I think he played the Ryman when I was in high school — it was like, ‘Oh that’s cool,’” Jody says. He remembers being struck by Prine’s childlike nature: “To find someone that was even more into Christmas than I was, you know, that was incredible,” Jody says. Prine had been known to keep a Christmas tree up year-round; sometimes, he even dressed up as Santa.

In 1996, Prine noticed a lump on his neck. He’d thought it was a blood vessel; it was actually stage-4 neck cancer. He would recover, but when surgeons removed a tumor, they took a chunk of Prine’s neck with it. When a doctor told Prine he may never be able to sing again, Prine replied, “Have you ever heard me sing?”

Fiona got used to Prine’s rhythms. He’d get going around noon, then go eat at a meat-and-three, like Arnold’s, which was a favorite. When Fiona was working around the house, she’d hear Prine in his den, reciting dialogue to old movies in real time. “John’s biggest thrill every day was when we figured out what we were having for dinner,” she says. She knows how thrilled he would have been to see his musical heroes pay tribute to him after his death. “He had such respect for Springsteen and Dylan, and in a way, for people that had made it ‘bigger than him.’ I mean, he was just, like, a fan.”

A few years ago, a typewriter arrived in the mail from Tom Hanks. It turned out Hanks was a huge fan, and heard from an interview that Prine liked to type out his lyrics. “He was excited like a little kid, that his favorite movie star had sent him a gift in the mail. He was blown away.”

Onstage, Prine was a gregarious storyteller, but in private he was quieter, more reflective. “You weren’t always sure he was listening at first,” says Jody. “But that was because he actually did. He wouldn’t respond right away. You’d say something, and he would wait a few beats. And you would think, ‘Do I need to repeat?’ He would be considering stuff.”

Jody remembers having a rough breakup in high school and opening up to John about it. “The guy who wrote ‘Far From Me’ obviously understood what I was feeling. He wouldn’t necessarily psychoanalyze stuff, but he would give you different ways to look at things.” Fiona says her husband could be hard to know in some ways. “There were things he found hard to articulate in conversations, things that scared him, maybe things he regretted,” says Fiona. “But he found a way to say it in his songs.”

Prine’s kindness was legend, especially among Nashville songwriters. “Him and Willie Nelson are the most revered people in the history of the backstage,” Snider says. “In the rumors that go around in our little world, there’s no weird ones about those two. There’s no, ‘And then he flipped over the table and said, “Fuck all of you.”’ Just about everybody else has one of those rumors.”

For years, Prine offered to adopt Jody, an offer Jody finally accepted in his twenties. He remembers the two of them going to the courthouse together, surrounded by young families. “Even the judge thought it was kind of sweet,” Jody says. “Because it was just two people deciding they want to be family together.”

In 2015, Prine’s manager Al Bunetta died. They had been best friends for decades, and Prine thought about retiring. He had just been through his second battle with cancer, having a portion of his lung removed in 2013. But he told his family he would keep going if they stepped in to take over his business. “I was like, ‘Well, OK, I don’t know anything about that, but as long as you keep your expectations low,’” Jody says, laughing. “John’s health was touch-and-go, but he did better when he was out on the road. We just wanted to keep that going.”

If the family was going to take over the business, they wanted Prine to record a new album. It had been a decade since his last one. Getting John to go into the studio “was like pulling teeth,” says Jody. Prine didn’t think a new album was necessary; his old songs kept finding new audiences anyway, and the idea of writing material that matched up to his classics made him nervous. “I don’t wanna just sit down and write a little couplet that’s kind of witty, or something,” he told me in 2016. “I’ve done that, and I don’t want to do it. I don’t want to repeat myself.” But his family convinced him to try. The following year, Fiona booked a room at the Omni. Prine brought in grocery bags full of old lyrics he’d jotted down, plus a few guitars, and strung the majority of the album together in less than a week.

The reaction to the Tree of Forgiveness was unlike anything Prine had ever experienced. The album went to Number Five on the Billboard 200, the highest debut of his career. He played some of his biggest shows ever, including a sold-out tour which kicked off at New York’s Radio City Music Hall. Suddenly, Prine had trouble walking through an airport without being recognized.

He seized the moment. He toured more furiously than ever, and his set lists grew to Springsteen-like lengths. At the Ryman Auditorium in late 2018, he played 29 songs, inviting up Jason Isbell and Amanda Shires, Todd Snider, the Secret Sisters, Sturgill Simpson, and more. “It was crazy,” says Jody. “We would have to tell him, like, ‘You don’t have to play that much. Some of your fan base is as old or older than you.’ But he just loved it once he was up there.”

“One of the last times I saw him, the two of us played a show in my hometown in Portland,” Snider recalls. “I got to show him my favorite pizza place. Him and Fiona loved it. That made my whole tour. John had been fighting. He had just beat cancer. But he was playing such amazing shows, and you could tell he wanted to play. One of the last times we sang together, at the Ryman last year, he grabbed my hand afterward and he looked at me, and he said, ‘I love you, Todd.’”

While Prine struggled with some aspects of his newfound spotlight, he loved being recognized by younger artists. In 2010, Justin Vernon, My Morning Jacket, Those Darlins, and others contributed to a tribute album, Broken Hearts and Dirty Windows, and in the following years his sound was embraced by a new generation of literate country and Americana musicians. “He loved the younger artists that reached out,” says Fiona. “The idea of John ever wanting to go to the Bridgestone Arena in Nashville] for a concert, that would be like, no. But when Kacey Musgraves had the last show of her tour there, there was nothing that was going to stop him from going. He had tears in his eyes that whole time, watching her. I mean, he was like a parent.”

In January, Prine traveled to Los Angeles to receive a Grammy Lifetime Achievement Award. As Bonnie Raitt sang “Angel From Montgomery” and talked about his influence on her, Prine could be seen smiling in the audience next to Fiona and Jody, with Jack Nicholson-style sunglasses on. “He got a really big kick out of it,” says Jody. “It was just funny to him, being there amidst all these really big celebrities. He’s a big reader of print media, so I didn’t have to explain to him who Billie Eilish was.”

In the final verse of “Paradise,” Prine sings, “When I die, let my ashes float down the Green River.” That’s exactly what’s going to happen. Half of his ashes will be spread on the river where he spent his favorite summers with his family, and other half will be buried in Chicago next to his parents.

While the Prine family cannot have a public funeral right now, they are finding ways to celebrate him. “I’m going to wash all of his Cadillacs, park them all in the driveway,” Fiona says. “I would never let him do that.” Jody says he’s remembering his father by celebrating “the small stuff, because that’s what he loves, like a hot dog. Or an ice cream cone. We were having ice cream last night, just thinking about how, after a show, he’d always have ice cream and pretend it was someone’s birthday and get a cake.”

The last song on Prine’s last album is “When I Get to Heaven.” In a spoken-word monologue, he talks about checking into a “swell hotel” and opening a bar called the Tree of Forgiveness, where he’ll hang out with his family, drink and smoke again, and even invite “a few choice critics.” “It came as the biggest surprise when I learned about how deep and yet uncomplicated John’s faith was in God and the afterlife,” Fiona says. “We always talked about how God pops up in so many of his songs. But he really did believe with no doubt that he would die and he would be in heaven.”

“He was able to imagine what heaven would be like just by imagining the parts of his life that he loved,” says Jody. “Because for him, heaven was not that different from his regular life. And that’s incredible.”

Additional reporting by Jonathan Bernstein