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John Prine: Essential songs to Remember the late American Songwriter

The past couple of weeks have been challenging for our nation in more ways than we could have imagined just months ago. In the world of music, a place many of us turn to for comfort and consolation in times of trouble, things have felt equally disheartening. With the loss of Kenny Rodgers, Jan Howard, and Joe Diffie in recent weeks, the news this week about John Prine’s death has felt like a twist of the knife for many of us. Prine, who was born in Maywood, Illinois (a western suburb of Chicago) and raised in a blue-collar family from Kentucky, carved himself a niche in the country-folk and Americana realm, and would call Nashville his home. Prine’s career path was certainly unconventional: he was drafted into the military and served as a mechanical engineer in Germany during the Vietnam era, never seeing combat but maintaining a sense of empathy and compassion for his fellow soldiers in South-East Asia (a sense of compassion which would permeate many of his finest records such as “Sam Stone”). After the war, Prine became a postman, but he found inspiration in the work of Johnny Cash and Bob Dylan, and calling upon lifelong inspirations such as the Carter Family and Hank Williams, he began to write and perform songs in Chicago. Prine was discovered performing in a bar in Chicago by Kris Kristofferson, and before long he began collaborating with Dylan and other songwriters, many of whom would eventually cover his songs (Bonnie Raitt, Johnny Cash, Willie Nelson, and Jackson Browne, to name a few).

To get a sense of Prine’s influence, you only have to take a brief look at what some of music’s greats have had to say about him. Bob Dylan identified Prine in a list of his “musical heroes,” and in an interview with MTV producer Bill Flanagan, Dylan proclaimed, “[Prine] writes beautiful songs,” and then described his work as “pure Proustian existentialism. Midwestern mind trips to the nth degree.” Bruce Springsteen, in a tribute to the late singer, recently hailed Prine as “a true national treasure and a songwriter for the ages.” Speaking to Prine’s character, Springsteen described him as “one of the loveliest guys in the world.” Indeed, the sense of empathy and kindness at the heart of Prine’s songs emanated from his own personal kindness, which fans and contemporaries alike have emphasized over the years.

Prine was known for his gruff, limited vocal range, which was exacerbated by recurring neck, throat, and lung cancer. The cancers compromised his ability to write and sing at numerous points throughout his career, but he never put down the pen or gave up singing. Perhaps Prine knew his stories had to be told. In 2018, Prine put out the album “The Tree of Forgiveness,” which was nominated for three Grammy’s and confronted notions of mortality and aging with Prine’s characteristic sense of humor and honesty. Indeed, it feels as though Prine, who had so many opportunities to give up and never did, was taken far before his time. But without further ado, we have a rundown of some of his finest songs, which we consider essential listening for anyone seeking to reconnect with Prine’s work or pay one last tribute to the startlingly honest, but reliably playful, John Prine.

“Your Flag Decal Won’t Get You into Heaven Anymore” (John Prine, 1971)

The seventh track on John Prine’s debut album begins with the instantly memorable line “while digesting Reader’s Digest in the back of a dirty book store / a plastic flag with gum on the back fell out on the floor.” Prine then details the obsessive story of a man who slaps American flag decals on his car in such number that he cannot see while he drives and winds up killing himself in a wreck. The song concludes with the man at heaven’s gate hearing from Saint Peter “Your flag decal won’t get you into Heaven anymore / We’re already overcrowded from your dirty little war.” The song confronts the troubling subject matter of America’s war in Vietnam and its Cold War militarism with wry humor, simple country instrumentation, and a blunt, yet thoughtful vocal from Prine. It is a fine example of his ability to sing honestly and seriously about fraught topics in American society with an unexpected twist of humor.

“Christmas In Prison” (John Prine, 1973).

“Christmas In Prison” is an improbable, waltzing, Christmas love song that seems to only spawn from a mind like John Prine. The song tells the story of a man in a kind of prison—perhaps literally, or psychologically—who pines for his lover. The song feels Faulknerian in style: its central character reminiscent of the raving savant, Darl, from As I Lay Dying. The song has moments of elaborate imagery, “The search light in the big yard / Swings round with the gun / And spotlights the snowflakes / Like the dust in the sun,” paired ironically with simple, humorous lyrics that read like a child’s letter from summer camp, “It's Christmas in prison / There'll be music tonight / I'll probably get homesick / I love you / Goodnight.” It is undoubtedly a goofy, minimal holiday song that is pleasant to hear, and under the surface, a surrealist masterpiece from Prine.

“Sam Stone” (John Prine, 1971).

Often considered one of John Prine’s greatest songs, “Sam Stone” details the life of torment of a heroine-addicted veteran who has returned home to his family, scarred from war and completely broken. The song contains the hauntingly poetic line, “There’s a hole in daddy’s arm where all the money goes, / Jesus Christ died for nothing I suppose”—a line Johnny Cash refused to sing in his cover of the song, but Prine considered one of his finest couplets in his five-decade career. “Sam Stone” gets to the heart of the profound anguish that accompanies many veterans who return home from war, yet the song never feels exaggerated or sensational. One of the concluding lines of the song is, for me, a testament to some of Prine’s best writing: “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.” The song is unsettling, yet an absolute essential in the Prine collection.

“Dear Abby” (John Prine, 1973).

In a pure sense, this may not be one of Prine’s greatest songs, but undoubtedly the song deserves a place on a list of essentials. “Dear Abby” is indicative of Prine’s ability to create a liminal space between traditional storytelling and songwriting, with a fair dose of humor throughout. The song traces the lines of correspondence between an advice columnist and its readers. Throughout the song, Prine details the complaints of readers of all walks of life who write to the columnist complaining of issues. Each time, the columnist responds in the same way, chastising the write-ins, “You are what you are and you ain’t what you ain’t / so listen up buster, and listen up good / Stop wishing for bad luck and knocking on wood.” I don’t think there’s a live recording of this song in existence that doesn’t have the audience laughing throughout.

“Paradise” (John Prince, 1971).

While Prine often concentrated on specific imagery and emotion, allowing listeners to fill in the story, he sometimes addressed social issues or events explicitly: “Paradise” is one such example. “Paradise” tells the story of the ecological degradation and decline of the town of Paradise in western Kentucky. Paradise, a fittingly incongruent name for the place Prine describes in the song, was the town Prine’s parents grew up in and one he visited as a child. Prine marries images from his childhood of the town with the realities of its exploitation, singing, “Then the coal company came with the world’s largest shovel / And they tortured the timber and stripped all the land / Well, they dug for their coal till the land was forsaken / Then they wrote it all down as the progress of man.” The song’s lyrics are often clear-cut and conspicuous, but its eerie, mournful chorus is what keeps the song with you: “And daddy won't you take me back to Muhlenberg County / Down by the Green River where Paradise lay / Well, I'm sorry my son, but you're too late in asking / Mister Peabody's coal train has hauled it away.”

“Hello In There” (John Prine, 1971).

Prine’s “Hello In There” explores the internal, hidden life of an elderly couple locked in a life full of memories without much more on the path ahead of them. The song is sentimental and unassuming, but addresses a variety of very troubling, human questions. Prine’s approach is modest and undecorated. For example, in the opening verse Prine sings from the elderly man’s perspective, talking about his children: “Well, it'd been years since the kids had grown / A life of their own left us alone / John and Linda live in Omaha / And Joe is somewhere on the road / We lost Davy in the Korean war / And I still don't know what for, don't matter anymore.” The feeling of powerless resignation in the narrator’s voice is heartrending and gripping as well as believable. Prine’s simplistic delivery and tone of voice feel honest, not maudlin or exaggerated. The song is poignant, however, it still finds a compassionate conclusion—as so many of Prine’s songs tend to do: “So if you're walking down the street sometime / And spot some hollow ancient eyes / Please don't just pass 'em by and stare / As if you didn't care, say, ‘Hello in there, hello.’”

“Knocking’ On Your Screen Door” (The Tree of Forgiveness, 2018).

The debut song on Prine’s 2018 album, “Knocking’ On Your Screen Door” is a testament to Prine’s capabilities as a singer and songwriter, even after numerous illnesses and countless surgeries. At its heart, “Knocking’ On Your Screen Door” is a song brimming with life. Prine’s central character is timeworn and rugged, without friends or family, but he still feels imbued with the spirit of life, even if that life is in the past. The character reminisces, ”I can see your back porch if I close my eyes now / I can hear the train tracks through the laundry on the line / I'm thinking it's your business, but you don't got to answer / I'm knocking on your screen door in the summertime.” Indeed, “Knockin’ On Your Screen Door” exemplifies Prine’s ability to keep moving and keep dreaming even as age and illness made daily life more challenging for him.

“Angel From Montgomery” (John Prine 1971)

John Prine’s eponymous debut album featured numerous songs that would form the heart of his catalogue and define him for generations to come, and “Angel From Montgomery” is one of the songs that stands at the forefront of the album. The album tells the story of a destitute middle-aged woman who seeks an outlet from the seemingly inescapable sufferings of her life. Other artists were so fond of the record that versions were recorded by Carly Simon and James Taylor, as well as John Denver in 1973 and Bonnie Raitt for her 1974 album Streetlights. The song is also notable for its instrumentation: it is more intricate than many of Prine’s songs, which tend to be dressed-down, and it is reminiscent of country-rock songs by Lynyrd Skynyrd and the Allman Brothers with its bluesy electric guitar and upright piano.

“Spanish Pipedream” (John Prine 1971)

Prine’s “Spanish Pipedream” tells the story of a soldier and a dancer who entices him into leaving his post and going off to the “country” to “Plant a little garden, eat a lot of peaches” and “Try an’ find Jesus.” The song is ultimately its title, a pipedream. Nonetheless, it’s an amusing escapist fantasy. The song displays Prine’s capacity to write fun and unencumbered songs: songs that a generation of people in parts of this country know by heart. And underneath the playful lyrics resides an awareness of the challenging realities of life: the war the soldier has to go fight and the “road to alcohol” that lies in front of the topless dancer at the bar. In this era where the facts of life are harder to grapple with, peaches and Jesus don’t sound half bad.

“When I Get To Heaven” (“The Tree of Forgiveness,” 2018).

The final track on John Prine’s final album couldn’t be more fitting. In “When I Get To Heaven,” Prine imagines his greeting with God, his activities in the afterlife, and even how he might forgive some critics, “those syph'litic parasitics!” This song features numerous spoken word verses and feels appropriately original for the final song on the album. Prine sprinkles in humor over the course of his discussion of his enterprises in heaven, and interestingly, the studio cut of the song features kazoos and the background noises of a baby playing and laughing. Even in contemplating death, Prine was thinking playfully and considering life. In one of my favorite lines in the song, Prine sings, “Yeah when I get to heaven, I'm gonna take that wristwatch off my arm / What are you gonna do with time after you've bought the farm?” It was that ability to whimsically condense deep thoughts, among so many other unique attributes, that made Prine so special to listen to.

Prine was a natural storyteller, his songs often sailed outside the bounds of countercultural movements and got at something deeper, something we might call American: not necessarily in its themes or subject matters, but in its expressions of compassion and empathy for people of all walks of life. We will deeply miss Prine’s earnest, gravelly voice, borne from a life of hardship, and we will miss his simple, almost deceptively smooth lyrics. But most of all, we are thankful for the courage he showed all of us in living, and for the time he dedicated to sharing his stories with us.

Written by Brennan White


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