Remembering John Prine, the Singing Mailman


By Maureen Leary, Youth & Family Programs Manager

Photograph of John Prine from the torso up, looking into camera. He wears a black suit and shirt, white bolo tie, and several rings.
John Prine
Photo credit: Danny Clinch. Used with permission from Oh Boy Records.

As the world marks more than a year of grappling with COVID-19, the enormous grief and struggle caused by the pandemic remain difficult to fathom. Among the profound losses, one from the performing arts world stands out. On April 7, 2020, while still in the early days of this crisis, singer/songwriter John Prine lost his life to COVID. The news was both stunning and tragic. A musical giant who had survived two bouts with cancer, Prine had received the Grammy Lifetime Achievement Award only two months earlier and was still actively producing albums up until his death at age 73. As evidenced by the outpouring of tributes that began at his passing and have continued in the year since, John Prine touched innumerable lives with his creative genius.

A wide-ranging and prolific songwriter, Prine improbably found lyrical inspiration in his early career as a mail carrier in the Chicago metro area. Having recently returned from service in the Army during the Vietnam War, the late 1960s found Prine pensive about the human condition and compelled to put to paper thoughts on topics many considered taboo. John Prine did not actively strive to make political statements with his songs, but he had an unswerving dedication to truth and authenticity that often led to social commentary. Throughout his years as a mail carrier, he closely observed details both mundane and exceptional, and showed an extraordinary ability to relate to experiences beyond his own. One of his most famous songs, "Sam Stone" explores the consequences of the trauma felt by veterans returning from conflict, while others examine ordinary domestic troubles. As Prine explained in a 2011 interview with Paste Magazine: “I knew there were a lot of GIs out there, who came out of the war and they weren’t quite right…. I knew there were homes where nobody was talking to each other, which became ‘Angel from Montgomery.’ … I knew there were kids who didn’t have fathers, and nobody ever acknowledged it, which became ‘6 O’Clock News.’… I saw all that. I knew, and I couldn’t figure out why no one would say anything.”  With ample opportunity for reflection while walking his mail route day after day, Prine deftly distilled timely concepts and transformed them into simple yet breathtaking artistry.

Image of John Prine album cover. Orange background with grey outline of suburban skyline. Black figure of mailman with mail bag.
Album cover © 2011.
Used with permission from Oh Boy Records.

His years as a mail carrier were such fertile ground for Prine's career that he later enshrined them with a double album entitled The Singing Mailman Delivers, produced by the label Oh Boy Records that he founded in 1981. Though not released until 2011, after Prine unexpectedly discovered the pristine reel-to-reel tapes while cleaning out his garage, the recordings date back to the beginning of Prine's journey as a singer/songwriter. The first album is a 1970 recording of the earliest versions of many of his popular songs, mostly written on his mail routes. The second album is a live show recorded at the Fifth Peg in Chicago, where Prine performed several nights a week while delivering mail during the day. As Prine recounts in the press release from the album, "I always likened the mail route to a library with no books. I passed the time each day making up these little ditties.”

The Fifth Peg is an appropriate venue for those early recordings of songs that would become iconic. It was not only his performing home for several formative years, but it was the spot where he was first discovered and propelled to prominence. John Prine was 23 and had been delivering mail for five years when film critic Roger Ebert wandered into his show and was blown away by Prine's raw talent. In 2010, Ebert reminisced on his blog about the chance encounter that helped launch Prine's career:  "Through no wisdom of my own but out of sheer blind luck, I walked into the Fifth Peg, a folk club on West Armitage, one night in 1970 and heard a mailman from Westchester singing. This was John Prine. He sang his own songs. That night I heard "Sam Stone," one of the great songs of the century. And "Angel from Montgomery." And others. I wasn't the music critic for the Chicago Sun-Times, but I went to the office and wrote an article."

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Host (starts mid-sentence): “…for us and all the way through the show. Okay. See you, John.

John Prine: This is a song I wrote a couple years ago, after I got out of the Army.


Sam Stone came home

to the wife and family

after serving in the conflict overseas.

And the time that he served

had shattered all his nerves

and left a little shrapnel in his knees.

But the morphine eased the pain

and the grass grew round his brain

and gave him all the confidence he lacked,

with a purple heart and a monkey on his back.

There's a hole in daddy's arm where all the money goes.

Jesus Christ died for nothin I suppose.

Little pitchers have big ears.

Don't stop to count the years.

Sweet songs never last too long on broken radios.

Sam Stone's welcome home

didn't last too long.

He went to work when he'd spent his last dime.

And Sammy took to stealing

when he got that empty feeling

for a hundred dollar habit without overtime.

And the gold rolled through his veins

like a thousand railroad trains

and eased his mind in the hours that he chose,

while the kids ran around wearin' other peoples' clothes.

There's a hole in daddy's arm where all the money goes.

Jesus Christ died for nothin I suppose.

Little pitchers have big ears.

Don't stop to count the years.

Sweet songs never last too long on broken radios.

Sam Stone was alone

when he popped his last balloon

climbing walls while sitting in a chair.

Well, he played his last request

while the room smelled just like death

with an overdose hovering in the air.

But life had lost it's fun,

there was nothing to be done

but trade his house that he bought on the GI bill,

for a flag-draped casket on a local hero's hill.

There's a hole in daddy's arm where all the money goes.

Jesus Christ died for nothin I suppose.

Little pitchers have big ears.

Don't stop to count the years.

Sweet songs never last too long on broken radios.

After Ebert's awestruck and unexpected review, there was seldom an empty seat in the Fifth Peg on a John Prine show night. Before long, Prine caught the attention of fellow musician Kris Kristofferson, and a fruitful friendship was born. Kristofferson's support directly led to Prine's early success. Immediately upon his arrival in New York City on his first visit there, Prine opened for Kristofferson at the famed Greenwich Village club The Bitter End. The next morning, he was offered a recording contract by Atlantic Records agent Jerry Wexler, who had been in the audience. His first album John Prine was released within a year, followed by more than two dozen albums over a luminous career spanning five decades.

Though he left us too soon, John Prine's musical mastery continues to offer gifts to the world. The compilation Crooked Pieces of Time: The Atlantic & Asylum Albums, released posthumously in October 2020, features remastered versions of seven studio albums from 1971 to 1980, packaged in mini replicas of the original LP jackets. With liner notes written by prominent music journalist David Fricke, the release showcases the remarkable talent and circumstances that led an unassuming mail carrier deeply interested in plumbing the depths of human experience to become a musical legend, a Grammy winner, and a member of the Songwriters Hall of Fame. John Prine rose out of the folk revival scene in Chicago as a young man who quickly made his mark in history through heartfelt stories and sincere emotion, ultimately becoming a music icon. Undoubtedly his fifty-year career will continue to bring joy to listeners for another fifty, and beyond.