John Prine returned to his hometown, Maywood, Illinois, in 1968. He was drafted a few years earlier, during the height of the Vietnam War, but avoided combat, instead serving in West Germany fixing trucks. He returned to his day job as a mailman, but his mind was elsewhere. Prine loved music; he’d had his dad mail him his guitar while he was in the Army, and he and his buddies would stay up late singing their favorite songs. He had his own ideas too. He wrote a few tunes as a kid, but it was on his mail route that he really started doing what he would go on to do for the rest of his life, better than nearly anyone else who did it. “You just had time to be quiet and think, and that’s where I would come up with a lot of songs,” he later told the Chicago Tribune. “If the song was any good I could remember it later and write it down.”

The songs were good. Prine was inspired by the countercultural folk movement of the 1960s, but the singular power of his style was also due to his careful attention to an earlier source. “I’m kind of based in country music,” he told Studs Terkel in a radio interview, recalling his family sitting in the kitchen on Saturday nights and tuning in to the Grand Ole Opry. The gallows humor and wordplay in Prine’s work made it country; the surreal imagery and willingness to confront taboo subjects were his own. The “singing mailman,” as an early review by Roger Ebert called him, would go on to acclaim rarely extended to country songwriters. By the next century, Prine had won not just two Grammys but also a PEN America award. Bob Dylan once commented on Prine’s “Proustian existentialism,” to which Prine responded, “I can’t even pronounce that!”

It never quite works to compare songs to writing on a page, but Prine’s backstory makes an analogy irresistible: His songs are like letters. They are personal dispatches, sometimes telling stories in the third person, sometimes conveying messages in the second person but always delivered with an intimacy that reflects the ways people really communicate. Many of his songs, like “Hello in There” and “Pretty Good,” both from his classic 1971 self-titled debut album, center on moments of human contact—or the lack thereof. They sound more like a correspondence with the listener than works of literature.

In an irony that would not have escaped his notice, it was a condition that has led us to limit human contact that led to Prine’s untimely death. He died of complications from Covid-19 on April 7 at Vanderbilt University Medical Center in Nashville. He had already beaten cancer twice, a 1996 surgery on his neck dropping his already gruff voice an octave. He leaves behind one of the most formidable bodies of work in American music, and that’s what he set out to do. “If I wanted to be a poet, I’d write poetry,” he once said in an interview. “I know what poetry is. I’m not writing poetry, I’m writing song lyrics.”

Prine’s epistolary style and his sharp eye for the vicissitudes of everyday life emerged fully formed on his debut album, recorded after his friend Steve Goodman took fellow Army veteran Kris Kristofferson to see him at a Chicago club called the Earl of Old Town. It includes some of Prine’s best-known work, which grew from his years in the military and the postal service. “Hello in There,” a heart-wrenching description of loneliness in old age, came from his observation of the residents of a nursing home on his mail route. Another, “Your Flag Decal Won’t Get You Into Heaven Anymore,” looked back with anger on the Vietnam War. “I wrote that one when I was a mailman,” he told Terkel. “I was delivering Reader’s Digest, and they put out an issue one month that gave everybody a free American flag decal. And that was just about the same time that there was all this talk going on about the silent majority and everything.”

Richard Nixon’s claims of a unified silent majority, referring to the reputed conservatism of the American masses, took place alongside his frequent appeals to the country music audience. During an address at the Grand Ole Opry in 1973, he drew a direct connection:

…the peace of the world for generations, maybe centuries to come, will depend not just on America’s military might, which is the greatest in the world, or our wealth, which is the greatest in the world, but it is going to depend on our character, our belief in ourselves, our love of our country, our willingness to not only wear the flag but to stand up for the flag. And country music does that.

Prine proved Nixon wrong. On songs like “Flag Decal” and “Sam Stone,” the story of a heroin-addicted veteran, he spoke with the voice of the silenced, refusing to be spoken for. He would continue to do so, without breaking from the tradition Nixon tried to claim. While some of the highest-profile folkies of the previous generation, like Joni Mitchell and Paul Simon, were moving in an upscale direction, with jazz harmonies and LA session musicians, Prine played it closer to the vest. The early ’70s albums Sweet Revenge and Common Sense sound more akin to the outlaw country coming out of Texas in those years than to the archetype of the confessional folk singer.

Prine was even the co-writer, with Steve Goodman, of “You Never Even Called Me by My Name,” the self-described “perfect country and western song” that became a hit for David Allan Coe in 1975. After a couple of verses of heartbroken pining, a spoken interlude notes that the song has lacked any references to “mama or trains or trucks or prison or gettin’ drunk.” The final verse ties them all together. Prine declined to put his name on the song, for fear of causing offense to his fellow country fans. But it’s the kind of joke you can only tell about something you love.

Prine closed out the 1970s and kicked off the ’80s with Pink Cadillac and Storm Windows, the former recorded at Sun Studios in Memphis and the latter at Muscle Shoals in Sheffield, Alabama, both sites where canonical American music was born decades ago. They were attempts at putting his songwriting in a commercial context, inching closer toward contemporary country and fashionably retro rock ’n’ roll; both had covers emblazoned with glamour shots of Prine, with a neatly trimmed mustache, hair slicked back, in an open blazer. But even in the shiniest packaging, he was a little too eccentric for stardom. He never recorded for a major label again.

By the mid-’80s, Prine had made the same move being taken at the time by alternative rock, founding an independent label, Oh Boy Records. It took him a moment to reconnect to his audience, but he did with 1991’s The Missing Years, produced by Howie Epstein of Tom Petty and the Heartbreakers. Featuring contributions from Bruce Springsteen, Bonnie Raitt, and Epstein’s boss, it won a Grammy for best contemporary folk album. Ironically, it was one of his less folky recordings, placing him nearer to the heartland rock that had become commercially viable by the early 1990s and the burgeoning Americana style that would come to be called alt-country. In 1999, In Spite of Ourselves, a collection of duets with female vocalists, took Prine back to the country songs he grew up listening to on the Grand Ole Opry. He followed it up with a sequel, For Better, or Worse, and a 2007 duet album with bluegrass singer Mac Wiseman with a title that could serve as a manifesto: Standard Songs for Average People.

For a songwriter with such an impressive body of work, Prine shone doing renditions of other writers’ songs. Among the last he recorded is an odd one, a version of Stevie Wonder’s 1984 hit “I Just Called to Say I Love You,” a digital single released after Prine’s final album, 2018’s The Tree of Forgiveness. Even for Wonder’s biggest fans—and I happen to count myself among them—the song can come across as corny, with its syrupy synthesizers and blunt declarations of love. You’re more likely to hear it at the drugstore than to put it on at home. But hearing it in Prine’s voice, you discover what you may have overlooked. What seemed overly earnest and straightforward reveals itself to be wry and self-effacing at the same time. It’s a testament not only to the brilliance of a deceptively simple song but also to Prine’s powers of observation, his ability to find depths in the ordinary and everyday that the rest of us tend to miss. Like many of his own best songs, it takes the form of delivering a message. No special occasion, nothing much to say. Just wanted to talk. It was always good to hear from him.