Iconic singer-songwriter John Prine dies at 73 of COVID-19 complications

CHICAGO — Talking about the singer-songwriter John Prine, Bob Dylan said, “Prine’s stuff is pure Proustian existentialism. Midwestern mind trips to the nth degree. And he writes beautiful songs.”

“Proustian existentialism?” Prine told the Chicago Tribune in a 2010 interview, shortly before returning to play at Chicago’s Old Town School of Folk Music, where he took guitar lessons as a teenager from nearby Maywood. “I can’t even pronounce that.”

That dichotomy between highest-level professional respect and the shoulder shrug of a blue-collar songwriting craftsman epitomized the career of Prine, which took him from postal routes in Chicago’s western suburbs to the city’s blossoming 1970 folk scene to, just this February, a Lifetime Achievement Award at the Grammys.

After decades of health troubles and being stricken with COVID-19 during the global pandemic of 2020, Prine died Tuesday at 73 in a Nashville hospital after being on a ventilator for more than a week. Rolling Stone magazine attributed news of the singer’s death to the singer’s family.

On the 2020 Grammys telecast, Bonnie Raitt acknowledged his career award by playing a radiant section from “Angel from Montgomery,” probably Prine’s best-known song and one of hers, too, an eloquent sketch of an old woman imagining something beyond her long, lonely marriage.

“How the hell can a person,” Prine’s character asked about her husband, “go to work in the morning, and come home in the evening, and have nothing to say?”

“My friend and hero John Prine, who is sitting right over there, wrote ‘Angel From Montgomery’ and so many other songs that changed my life,” Raitt said, and the camera shifted to the somehow still elfin face of Prine.

He didn’t get a lot of mainstream pop spotlight moments like that. But his career produced a steady supply of songs like “Angel” that were instantly unforgettable and frequently covered by others: stories of complex characters told with grace, humor and a reverence for the poignance of life.

“They were unique,” said Ed Holstein, the Chicago folk scene veteran who came up at the same time and was the same age as Prine. “I was kidding with John one time. I said, ‘John, when I talk to people like the air-conditioning guy or the plumber, they say, “I tell ya, the guy I like is John Prine.” They don’t care about the other guys.’ And John said, ‘Yeah, and I’m also big with pest-control people.’

“I think that’s it. People can relate to his songs.”

“We’ve lost not only one of the greatest singer-songwriters that the world’s ever had, but in my mind one of the only ones, because of the voice,” said Robbie Fulks, the veteran Chicago singer-songwriter. “There aren’t a lot of people that actually have their own voice, that don’t sound imitative in any way.

“That was John. In songs about death, betrayal or loneliness, it seems to always include a light sense of irony or humor or absurdity — everything mixed together in life, the way that it is. You just feel who he is when you’re listening to his songs on a record. There’s nothing between that brain and your heart when you’re hearing his music —despite the technical prowess and the mastery he uses. Those tools don’t stand in the way somehow. It’s like the greatest magic act in all of singer-songwriterdom.”

The achievements of Prine’s lifetime included two Grammys for best contemporary folk album, for 1992’s “The Missing Years” and 2006’s “Fair & Square,” plus nine other Grammy nominations. In 1973, he was up for best new artist alongside the Eagles, but the band America, who sang the nonsensical “Horse with No Name,” won.

The Recording Academy made up for that oversight in 2015 when it put Prine’s self-titled debut album, from 1971, into its Hall of Fame for “recordings of lasting qualitative or historical significance.”

“Angel from Montgomery” was on that record, an extraordinary feat of empathy for his character from a writer not yet 25. So was “Hello in There,” a wrenching take on an older couple feeling left behind and overlooked that Bette Midler and Joan Baez have made staples of their live set lists. So was “Sam Stone,” another entry in the folk canon, Prine’s tale of a veteran who returns from Vietnam addicted to morphine.

“There’s a hole in daddy’s arm where all the money goes,” the chorus of “Sam Stone” begins. “Jesus Christ died for nothin’, I suppose.”

Prine grew up in Maywood, Ill., to parents whose roots were in Kentucky. An older brother brought him along to guitar lessons at Old Town in the early 1960s. He served in the Army in West Germany, as a mechanic, and when he came back worked as a postman, where his mind and his musical inclination began to kick in.

“I wrote ‘Sam Stone’ and ‘Hello in There’ on the route,” he told the Tribune in 2010. “When you’re a mailman on the same route for a couple weeks there is nothing to do. You just try to drop the right mail at the right house and make sure you’re on the right street … I likened the mail route to being in a library without any books. You just had time to be quiet and think, and that’s where I would come up with a lot of songs. If the song was any good I could remember it later and write it down.”

He was hanging out at the Fifth Peg, a club opened on Armitage Avenue across from the Old Town School by people associated with it, Holstein said.

At an open-mic night, Prine recalled, “I made a remark about the people that were getting up to sing: ‘This is awful.’ So the people I was sitting with said, ‘You get up and try.’ And I did. I remember playing ‘Sam Stone,’ and the crowd just sat there and looked at me when I was done. And I thought, ‘Uh-oh, I’m in trouble.’ But it was like they were stunned, and then they applauded.”

The owner asked him back to play his own sets. The first, brief assessment of him in the Tribune came Oct. 11, 1970, in the On the Town column: “John Prine, back from his army reserve duty, is singing folk music at the Fifth Peg on Fridays and Saturdays. Fleming Brown, a folk singer whose opinion we respect, says: ‘We’ve got a genius on our hands.’”

This was two days after the late movie critic Roger Ebert went off topic to sing Prine’s praises in a Sun-Times music review “and that busted things wide open,” Prine said.

“He’s closer to Hank Williams than to Roger Williams,” Ebert wrote, “closer to Dylan than to (Phil) Ochs. ‘In my songs,’ he says, ‘I try to look through someone else’s eyes, and I want to give the audience a feeling more than a message.’”

The Chicago folk scene was already hopping, Holstein said, perhaps the last place in the country where there was a folk scene, and Prine’s talent was an electric addition. “Right away, he had a bunch of songs, four or five,” Holstein recalled. “A lot of us had maybe one or two that were really something. He had a bunch.”

And Prine’s star in that scene, along with friend Steve Goodman, kept growing. Kris Kristofferson saw him one night at the old Earl of Old Town and began championing his cause. In 1971, Prine’s debut record came out.

In addition to getting him the best new artist nomination, by July of 1972 nine of the 13 songs on it had been covered by other artists, including Dylan and fellow folk hero Joan Baez, the Tribune noted in a profile of “Chicago’s shot-and-a-beer lyricist.”

Now-revered albums seemed to flow from him throughout the 1970s, including “Sweet Revenge,” “Common Sense” and “Bruised Orange.” In 1980 he moved to Nashville, and later that decade became one of the first artists to start his own label, Oh Boy Records. The pace of production slowed, but the quality remained high.

“What you ultimately want is a song that you’ll want to sing forever,” Prine told CBS’s John Dickerson in a recent interview. “It might go to No. 1, and, tag, you’re it.”

In his writing, he told Dickerson, “I’m real picky about syllables … You want to have a syllable for every note, or at least the word has to hit your ear right.”

The spark of “Sam Stone,” he explained, was the idea of a broken radio, which fed the last, devastating line to that chorus: “Sweet songs never last too long on broken radios.”

“It takes something like one strong image to pull the rest of it out,” Prine said. “And then from there on in, it’s more of a craft. But you’ve got to have that one burning coal.”

Along the way he had three marriages, his last to Fiona Whelan Prine, who also managed him and who got COVID-19 in March 2020 just before he did but recovered. He had cancer twice, losing part of his throat in the late 1990s, part of his left lung in 2013.

Beyond Dylan, accolades have come from scores of fellow musicians through the years, including Johnny Cash. Pink Floyd’s Roger Waters once said Prine’s “is just extraordinarily eloquent music — and he lives on that plane with Neil Young and Lennon.”

The songwriter also remembered his Chicago roots. Even after moving to Nashville, he showed up at FitzGerald’s in Berwyn several times during the 1980s to sit in with his old backup band, the Famous Potatoes, former club owner Bill FitzGerald recalled.

And in June of last year he made it point to attend a private event to benefit the small, struggling Val’s Halla records in Oak Park; the late owner Val Camilletti was an old friend.

Prine was in town at the time for a Ravinia Festival appearance, still touring behind 2018’s “Tree of Forgiveness,” his first collection of original songs in 13 years and his last.

To get it out of him, his family rented him a hotel room in Nashville by the Country Music Hall of Fame, and sent him in there with his guitars and the boxes full of song and lyric ideas that had piled up over the years.

“I’ll get some of my best ideas behind a steering wheel rather than behind a guitar,” he told CBS, explaining that it was too hard to write in his house. “When I first started writing songs that was my getaway from the world … but now it’s my job.”

A week later he was in the studio, recording what would be hailed as another gem, helped out by the likes of Brandi Carlile and Jason Isbell. It won him another Grammy nod and saw him return, triumphantly, to the Chicago Theatre.

The voice, ravaged by age and cigarettes and the throat surgery, was so gruff and unsteady that he compared it to a distant radio signal. “It gets pretty, then it gets ugly, and then it gets pretty ugly,” he said from the Chicago stage.

No matter. The songs from the new record —and the ones that he had played a thousand times and could stand to play still —still resonated with longing and irony and sharp, sly humor. They were songs whose thematic complexity belied just how damned hummable they were, John Prine songs.

The last one of those on his last record is called, fittingly, “When I Get to Heaven,” and it imagines heaven as a kind of no-holds-barred neighborhood bar.

“I went to see him a few years ago at Symphony Center,” Holstein recalled. “He was just like he was at the Fifth Peg, really. He had a couple of great musicians with him and some great sound equipment. But it was the same show. I mean, how do you get intimate with 2,800 people? He did that.”