Remembering John Prine, the Ultimate Songwriter's Songwriter

John Prine wasn’t the most famous singer-songwriter of the past 50 years, or the most mythologized, but he might have been the most intensely beloved. People held onto John Prine’s songs, clutched them as if they offered proof. If his songs were allowed to exist in the world—so simply written, so profoundly beautiful—surely there was room for other good, decent things, too. The people in his songs lived such vivid lives that all he had to do during a show was say their names—Donald and Lydia, Loretta and Davey—and people would whoop, as if he had mentioned their mother.

Prine was born 10 miles west of Chicago in 1946, his family’s third son. His father worked in a beer can factory and was a leader in his union for about 30 years; if you were fictionalizing blue-collar bonafides, you couldn’t top that. As a child in suburban Maywood, Illinois, he was prone to spells where he simply stopped paying attention to everything. “I couldn’t concentrate on anything besides daydreaming,” he once said. “My brother saw this… and he saw music as a way of getting through to me.” Dave Prine, the family’s eldest son, sat down and taught John a few chords on guitar. “From there,” he remembered, "it was me sitting there alone in a room singing to a wall.”

Unlike other musician hopefuls, Prine didn’t drop out of school, or move across the country to pursue a recording career. After graduating high school, he took up a mail route, which gave him plenty of time to daydream and make up little songs. His postman stint turns up in every piece of writing about Prine, but it’s hard to resist, and Prine never did; he once released a rarities collection called The Singing Mailman Delivers. The job seemed to illustrate something essential about Prine—the everyday nature of it, the dutiful handling of other people’s belongings. His route was briefly interrupted in 1966 after he was drafted into the Army and stationed in West Germany, where he ran a motor pool and worked on construction equipment; when he came back two years later, he resumed stuffing mailboxes and humming under his breath.

If not for a few beers one night at an open mic, this might have been the beginning and the end of the John Prine story. But his friend dared him to go onstage after Prine grumbled about the talent. He sang a song he’d just written that he was calling “Old Folks,” later renamed “Hello in There.” The lyrics peer into the minds of an old couple, losing touch with the world and each other. As he sang it to audiences of increasing size for the next four decades, he aged into the circumstances of his characters, but on that night in Chicago, he was just a 23-year-old man, a flat twang to his voice that felt much more suited to small talk than to singing. He was untrained, a little shaky. But when he finished his set, which also included early versions of “Paradise” and “Sam Stone,” there was such a heavy silence that he was alarmed. Moments later, the applause began.

Prine never really strained for career opportunities—they sort of ambled up to him, like dogs coming home. Soon, he had a weekly gig where he kept 50 cents of each customer’s admission; 12 people showed on his first night. A singer-songwriter friend convinced Kris Kristofferson and Paul Anka to come hear him; Prine had to be persuaded to play for them. Kristofferson connected him to Atlantic Records, which offered him a contract in 1970. On Prine’s self-titled debut LP, he recorded with the same musicians who played on Elvis’ “Suspicious Minds” and Dusty Springfield’s “Son of a Preacher Man.” Released in 1971, it likely remains his single best-known recording.

He stayed afloat in the major-label system for a while, allowing multiple label heads to discover just how incapable he was of writing a hit. His songs were too digressive and they almost never stopped at the three-minute mark. Like Leonard Cohen, Prine often watched his songs ascend to unimaginable heights when other artists sang them—Dolly Parton, Bonnie Raitt, Tammy Wynnette, Willie Nelson, Joan Baez, dozens more. His songbook was a buffet table for whoever wanted to avail themselves. He never stopped providing, even if he never quite ascended to another level of fame—he was always just John Prine, one of the greatest songwriters who ever lived, forever hiding in plain sight.

Perhaps that’s why Prine became a sort of folk hero for people who felt overlooked, instead of forgotten; forgotten implies a romance that his characters never allowed themselves, and Prine himself never really indulged in that kind of melodrama. He wrote in the simplest and most profound possible statements, and preferred to let facts do their own work. “Writing is about a blank piece of paper and leaving out what’s not supposed to be there,” he remarked in the liner notes to his 1993 anthology Great Days. Things simply were in John Prine songs; whatever adjective you wanted to add after the word “were” was just your own story, no longer the truth.

In 1978’s “Bruised Orange,” he watches an altar boy get struck by a train. It’s gruesome and horrifying, but Prine takes time to notice that the train was coming “so slow,” as if to suggest that the altar boy had time to get out of the way. The chorus throws up its hands at the idea of throwing up your hands: “You can gaze out the window get mad and get madder/Throw your hands in the air, say ‘What does it matter?’/But it don’t do no good to get angry/So help me I know/For a heart stained in anger grows weak and grows bitter/You become your own prisoner as you watch yourself sit there.” Watching yourself sit there—there might not be a more prototypical Prine image, the narrator looking down at themselves in their plight and laughing slightly.

Everything is at least a little bit funny in a John Prine song. (Only he could have convinced folk artist Iris DeMent to sing the words “sniffin’ my undies.”) Even his bitterest songs sound jovial, as if a shit-eating grin could sing. “Sam Stone,” his fantastically bleak portrait of a shattered war veteran, written years before the plight of Vietnam vets became common singer-songwriter fodder, lands on a hundred wry little grace notes. The 1971 song may depict the life of a junkie who slowly bottomed out and was buried on a “local hero’s hill,” but there isn’t a single strident moment in it. The images he evokes aren’t ha-ha funny—the most famous line is “There’s a hole in daddy’s arm where the money goes”—but they are unimpressed with darkness for its own sake. We usually tell our worst stories with a mixture of resignation and good humor, since we’ve already survived them, and Prine’s music emanated from this frequency. “Sweet songs never last too long on broken radios,” he sang in the chorus. But they lasted a little while.

Prine’s songwriting has always been easeful, even conversational, around death. On “Lake Marie,” he wrote about people found dead in the woods as if they were leaves in a gutter. He wasn’t pitiless, just matter-of-fact. Prine stared down on his own mortality as well, recovering from not one but two bouts of cancer before his death this week of complications from COVID-19. When I met him in 2018, he already seemed fragile; he had a peculiar ambling gait, as if he was being jerked by marionette strings, and his guttural rumble reminded me of my two-packs-a-day childhood babysitter, even though he hadn’t touched a cigarette since the ’90s.

He was promoting The Tree of Forgiveness, his first album of original songs in 13 years, and we spent a good portion of time discussing death. “That’s what comes with age,” he lamented. “You end up with more people on the other side than there are here. I hear people my age talking about this all the time: The worst thing about them getting older is less of their friends are around. But I’ve still got most of my good buddies, so that’s good.” I asked him what he enjoyed about being old, now that he’d made it there. “If there’s only one chair left, you’ll get it,” he said, smiling. “An extra piece of cake if your wife’s not around. The good things in life, you know?”

He told me a story about “Bruised Orange,” the song with the dead altar boy. Prine witnessed the accident, and he remembered watching parents gather into “a tribe of grief” to find out whose child had been taken. Years later, he received a letter from the mother of that boy. “She could have said, ‘Why did you have to tell my son’s story?’” he mused. “But she thanked me profusely. She told me that there was a sense of closure to it.” He considered responding to her, but decided against it. “I thought: I got the letter. That’s enough.”

CORRECTION: A previous version of this story erroneously stated that Prine served in Vietnam.