John Prine: 25 Essential Songs

Prine’s most widely known song is an indelible portrait of “a middle-aged woman who feels older than she is.” The song’s stripped-down country-rock arrangement belied the intricacy of Prine’s lyrics, which home in on details like the flies buzzing around the kitchen sink and the rodeo poster that sends her into a reverie of youthful recollection, and its matter-of-fact description of marital stasis and midlife depression were groundbreakingly real. “Angel From Montgomery” became a country standard, covered most famously by Bonnie Raitt, whose slow, soulful version highlighted the song’s theme of emulsified female desire. She performed it movingly earlier this year at the Grammys, when Prine received a Lifetime Achievement Award. J.D.

The opening track to Prine’s self-titled 1971 debut, “Illegal Smile” became an anthem for weed-smokers — despite the songwriter claiming it wasn’t really about that. Lyrics about having “the key to escape reality” and paranoid run-ins with the law might suggest otherwise, but it’s Prine’s rhythmic delivery that makes the song so inebriating. He phrases it like a children’s sing-along, emphasizing the final two syllables of each line: “I chased a rainbow down a one-way street — dead end/And all my friends turned out to be insurance — sales men.” The imagery is trippy throughout, but it’s Prine’s ad-libbed rhymes at the song’s end that double down on the childlike wonder: “Well done/Hot dog bun/My sister’s a nun.” Such fun. J.H.

There’s a lot of advice in Prine’s tale about a soldier and a topless dancer who run off together to live the good life. For starters: blow up your TV, throw away your paper, go to the country, build you a home. It all sounds especially enticing today, if increasingly hard to manifest — it’s a pipe dream after all, as Rolling Stone pointed out in its 1971 review of Prine’s debut album. Prine himself never went as far as blowing up his own TV, but he did mount an attack on his own boob tube, telling Performing Songwriter, “I used to keep a small bowl of real fine pebbles that I picked up on my mail route, and if somebody said something really stupid on T.V. I’d throw some at the screen.” J.H.

A sentimental recollection of home that’s also an unsparing description of predatory capitalist devastation, “Paradise” is Prine’s ode to the tiny mining town in Western Kentucky where his parents met. “Peabody Coal and Mining bought up all the land down there, and they tore the whole town down; they strip-mined it,” Prine said, introducing the song during the 1970 performance that would be released in 2011 as part of The Singing Mailman Delivers. It became a beloved standard – recorded by the Everly Brothers, John Denver and Johnny Cash – much to Prine’s surprise. “I wasn’t even going to record it because I didn’t think anybody would be able to pronounce ‘Muhlenberg,’ ” he said. J.D.

Prine wrote this heartbreaking tale of a heroin-addicted veteran for his first album, not long after he returned home from serving in the Army himself. “Sam Stone” immediately became one of the songwriter’s most signature tunes, filled with shattering one-liners like, “There’s a hole in daddy’s arm where all the money goes/Jesus Chris died for nothin’, I suppose.” Forty-seven years later, Prine told this magazine that that couplet was the one he was most proud of in his entire career. “A lot of soldiers came home and got hooked on drugs,” he said. “I was just trying to think of something as hopeless as that. My mind went right to, ‘Jesus Christ died for nothin’, I suppose.’ I said, ‘That’s pretty hopeless.’” J.B.

Inspired by John Lennon’s reverb-heavy vocal on the Beatles’ “Across the Universe,” Prine thought about “hollering through a hollow log, trying to get through to somebody.” He spun that notion of trying to connect across a vast divide into a uniquely empathic song that inhabited the life of an elderly couple — from the apartment they shared when they were younger, to the kids who’ve grown up and left (or, in the case of Davy, died “in the Korean War/I still don’t know what for”), and the quiet, isolated existence they now soldier through. In classic folk tradition, Prine ends by addressing the listener, asking that we reach out too: “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.’ ” J.D.

Prine wrote this gorgeous meditation on nostalgia in his ‘65 Chevelle, on the way to one of his earliest gigs at the Fifth Peg in Chicago. In part, it’s about a buried childhood memory of thinking his brother had gotten lost at a carnival. “I thought I had come up with a pretty sophisticated melody in my head,” he said. “I was surprised to find out it had the same three chords that all my other songs have.” Prine frequently performed the song with his musical partner Steve Goodman (the definitive version is their live duet on Prine’s Great Days anthology), and for decades he dedicated the song to his late friend each time he played in. The two-verse tale of someone haunted by their lifetime of memories is Prine at his sentimental best, and he even invented a new word along the way: “Memories, they can’t be boughten.” J.B.

Leave it to Prine to write a deeply unconventional Christmas song and a deeply unconventional love song, all at once. “Christmas in Prison” is apparently about a homesick inmate pining for his lover, though Prine indicated the incarcerated subject may not be in a literal cell: “It’s about a person being somewhere like a prison, in a situation they don’t want to be in,” he said. “And wishing they were somewhere else. But I used all the imagery as if it were an actual prison.”

The tune is a sweet, sentimental waltz; the lyrics manage to be both funny and wildly evocative. The inmate aches for his beloved while piling up striking images like notches on a cell wall: “She reminds me of a chess game/With someone I admire/Or a picnic in the rain/After a prairie fire.” As for the holiday setting, Prine loved the season: As a bachelor, he kept a Christmas tree up in his house all year round. C.H.

Prine’s father Bill was a factory worker and union president who introduced his son to country music. The younger Prine says he always wrote with hopes of impressing his father, which he finally did on “Paradise,” about his parents’ Kentucky home. But Bill Prine didn’t live to see his son’s success; just before Prine’s first album came out on Atlantic Records, he died of a heart attack on the front porch in Maywood, Illinois. John had been with him earlier that day.

Just like he did with every trauma in his life, John wrote about it. Over several verses he evokes the helplessness, anxiety and pain he was feeling: “The cuckoo clock has died of shock and the windows feel no pane,” Prine sings, “The air’s as still as the throttle of a funeral train.”

After an ominous series of observations, only in the last verse does Prine tell us who the song is about: “My father died on the porch outside on an August afternoon/ I sipped bourbon and cried / With a friend by the light of the moon.” P.D.

Prine wrote this young man’s blues about an early breakup, the same one that inspired his debut album masterpiece “Far From Me.” “The first time you get your heart busted, you never forgive,” he said years later. “Especially if you’re a writer.” The song was part of Prine’s earliest repertoire in Chicago folk circuit, but he hung onto it for a while, making it a downcast highlight of his third album, 1973’s Sweet Revenge. In this two-verse torch song, young heartbreak is recast as a torrential storm, and Prine is left with only a sad umbrella to “hide the pain while the rain makes up [his] mind.” But “Blue Umbrella” will always be remembered for its chorus, with its unforgettable depiction of feeling young, lost, and alone: “Just give me one extra season,” Prine begs. “So I can figure out the other four.” J.B.

This dark surrealist tale is based on Prine’s real-life traumatic childhood memory of witnessing the aftermath of a local altar boy who was killed by an Illinois commuter train. Prine juxtaposed the violent tale, which both opens and closes the song, with an unusually anthemic chorus (inspired by Bob Dylan’s “The Lonesome Death of Hattie Carroll”) about fighting against our worst tendencies and a seemingly unrelated second verse about kissing a black-haired girl on a park bench. “My head shouted down to my heart, ‘You better look out below,’” he sang. “When I’m writing, I’m never sure if it’s really facts I’m getting or if I’m making it up,” the songwriter said in 2017. “There’s no line.” Years after Prine released the song, the parents of the altar boy sent Prine a letter thanking him for it. J.B.

On this upbeat stomper off Bruised Orange, his excellent, undersung third album, Prine combines snapshots from various different chapters of his life – from his first job working at a local drive-in to his army days – and strings them together with a chorus about the importance of forgiveness. The song is full of hilarious observations pulled straight from real life. “On my very first job I said ‘thank-you’ and ‘please’/They made me scrub a parking lot down on my knees/Then I got fired for being scared of bees/And they only give me fifty cents an hour.” Prine admitted after writing the song that he indeed was terrified of bees. P.D.

Not a literary masterpiece, just a compact, easygoing tune that seems to effortlessly sum up the life cycle of a relationship from first kiss to last goodbye with a perfect mix of matter-of-fact honesty and genuine wonder at the cheesy depth of the ritual. “You know what they say/They pledge their love forever/Then they add a day,” he sings, proudly adding his own two cents to one of pop music’s richest songwriting traditions. Rachel Peer’s subtle harmony vocals give the song an extra shading of bittersweet beauty. J.D.

Prine wrote this tale of the double standards facing a single pregnant mother with legendary Nashville songwriter Bobby Braddock in the early eighties. “I wrote down 15 titles, including one called ‘Children Having Children’ and ‘Unwed Fathers’” Prine later said. “I was reading the list off to him, and all the lights went on with those two. We kind of combined them and went right into it.” The song, later recorded by Tammy Wynette and Johnny Cash, was the highlight of his 1984 album Aimless Love, where Prine sang it as a duet with then-wife Rachel Peer. In later years,it became a duet standard for Prine, who would perform it with friends like Margo Price, Iris DeMent and Amanda Shires. J.B.

Written on the patio of a Nashville hotel and released on Prine’s 1986 album German Afternoons, “Let’s Talk Dirty in Hawaiian” is at once one of the greatest vacation songs and one of the greatest sex songs ever written — pure playful fun stuffed with wonderful, hilarious wordplay. “It’s a ukulele Honolulu sunset.” Prine sings against inviting geographically appropriate accompaniment, “Listen to the grass skirts sway/Drinking rum from a pineapple/Out on Honolulu Bay/The steel guitars all playing/ While she’s talking with her hands/ Gimme gimme oka doka make a wish and wanta polka/Words I understand, hey!” He described it as “the kind of song that keeps you out of the shrink.” J.D.

Written in the aftermath of a bad relationship, this 1986 ballad is John Prine at his most romantically destitute. “It was a song about a break up,” he said in 2016. “I had a picture in my mind of one of the astronauts of the 1950s with his face all contorted by G-force. I was thinking of somebody’s heart being pulled apart by G-force like that.” Just as “Angel From Montgomery” became best known from Bonnie Raitt’s rendition, “Speed of the Sound of Loneliness” belonged to Nanci Griffith, who included a duet of the song with Prine on her 1993 album Other Voices, Other Rooms. But the simple three-chord devastation in this tale of two lovers who’ve grown far, far apart was pure Prine, resulting in perhaps the most heartbreaking line in his songbook: “You come home straight/And you come curly,” he sang. “Sometimes you don’t come home at all.” J.B.

Written at the last minute as he wrapped up work on his 1991 LP, The Missing Years, “Sins of Memphisto” is a lovely, laidback literary tour-de-force full of classic rhymes (“Sally used to play with here Hula Hoops/ Now she tells her problems to therapy groups”), absurdist imagery and careful everyday observation, spun into a beautiful meditation on love and aging, youthful freedom and lost innocence. The song’s cast of characters include Adam and Eve, Lucile Ball and Ricky Ricardo, Esmeralda and the Hunchback of Notre Dame, a kid riding his bike around a town he can’t wait to escape and a Grandpa “on the front lawn staring at a rake/Wondering if his marriage was a terrible mistake.” It’s all delivered with the a tender late-afternoon prettiness that makes its uncomfortable realizations about life go down like a sip of Orange Crush. J.D.

Leave it to John Prine to turn an account of his divorce from second wife Rachel Peer into one of his most big-hearted moments, the tale of a broken heart healing itself through compassion. The song culminates in Prine’s most devastating distillation of what happens when two people grow apart: “Your heart gets bored with your mind/And it changes you.” “All the Best” anchored Prine’s 1991 comeback triumph The Missing Years, the album’s purest distillation of lost love and blossoming romance with his to-be third wife Fiona. “Having recently acquired my second divorce,” Prine said before introducing “All the Best” in 1990, “about a month later the song truck pulled up and dumped a bunch of great songs on my lawn.” In other words, he had “so much love that he cannot hide.” J.B.