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A Big Old Goofy World: 13 Essential John Prine Deep Cuts

I didn’t think John Prine would die. I always thought he would disappear into some dark jungle, carried along by a herd of wild pachyderms. Or he would ride a steamer out over the horizon, waving to those on shore. Or he’d just ascend on wings right up to the pearly gates, where he’d regale St. Peter with a few songs on harp. Grounded as he was in worldly eccentricities, Prine always had an air of the mystical about him, channeling so much humor and humanity into his songs that he seemed somehow superhuman. He was certainly a hero, especially in Nashville, but he was the consummate songwriter for every generation that came after him. That he should die from something so mundane as COVID-19 must surely be a cosmic mistake. Doesn’t the universe know who John Prine is?

He often wrote about death during his 50-year career, even when he was an invincible young man. He pondered the afterlife on songs like “Please Don’t Bury Me” (in which he bequeaths his arms to Venus de Milo) and “He Was In Heaven Before He Died” (inspired by his father’s passing in 1971). He wrote like he wasn’t afraid, but he sang like he was trying to puzzle something out. Death was funny and unfair and perhaps Prine’s greatest subject as a songwriter, and he took to it like he wanted to console us, to ease us into the inevitable. He sang them to comfort us, to take away some of death’s sting, and to give us all a good laugh before we shuffle off into the unknown.

I met John Prine once. I was on assignment, and he wanted to meet up at Arnold’s, his favorite meat-and-three in Nashville. He’d picked it based on the day of the week: They had country-fried steak that day. He took a table near the door, which put him in the path of well-wishers and fans who recognized him and wanted to shake his hand or tell him how much they loved a particular song. He knew the staff there by name, and now that I think of it, I never saw him place his order. His food just arrived. He tucked into his mashed potatoes and mac & cheese with glee, and he answered every question with a sly smile or a knowing chuckle, relishing certain stories no matter how many times he’d told them before. After he finished off his banana pudding, he propped one of his feet up on the table to show off his new boots. Small, ordinary pleasures became something to relish.

After lunch he drove his enormous Cadillac (which he admitted had a Christmas tree in the trunk, stowed away like a hostage) to the offices of Oh Boy Records, the label he co-founded in the early 1980s with his friend Al Bunetta. Inside the former home that had been converted into offices, there were two enormous dogs on the wall, drawn by the cartoonist John Callahan, and a Christmas tree in the corner that was up year round. The major labels around Nashville didn’t know how to market him and weren’t very willing to try, so he struck out on his own. For 40 years he was the main artist on the roster, although he did release excellent records by Kris Kristofferson, Todd Snider, and Kelsey Waldron. His business influence almost matches his musical influence: Oh Boy is the longest-running independent label in town and a direct model for Thirty Tigers, Third Man, Jason Isbell’s Southeastern, and every other record company in town. He proved there were ways a musician could take the reins of their career, release their own material on their own terms, maybe weather as many downs as ups but still be able to sleep at night.

John Prine seemed to emerge as a fully formed songwriter, one whose gift for wordplay and character were already intact by the time he picked his first notes. He came up in the Chicago folk scene, delivering mail by day and by night singing at clubs like the Fifth Peg and the Earl of Old Town. Kristofferson reportedly said Prine was so good they’d have to break his thumbs. His 1971 self-titled, recorded in Memphis with Elvis Presley’s backing band, is about as perfect a singer-songwriter album as you could hope to hear. Most songwriters would kill just to pen one of these tunes, whether it’s the nostalgic eco-blues “Paradise” or the rousing anti-war sing-along “Your Flag Decal Won’t Get You Into Heaven Anymore” or the heartbreaking “Angel From Montgomery,” a Winslow Homer painting set to music.

He couldn’t top it, but who could? Throughout the ’70s and into the ’80s, he released a string of good to great albums, musically and lyrically adventurous but so idiosyncratic that he never truly fit within a scene. He wasn’t a country outlaw, nor was he one of those sensitive singer-songwriter types out on the West Coast, nor was he a mainstream country crooner down on Music Row. He wasn’t a sex symbol like Kristofferson nor a counterculture figure like Willie Nelson. His records didn’t chart, and his songs usually did better when other people sang them, like Bonnie Raitt or David Allen Coe. He was never what you would call popular, but he got by in the shadows, as though his career frustrations might be the punchline of a pretty funny cosmic joke.

And that just meant he could age all the more gracefully. When his peers were settling into second careers as nostalgia acts, Prine was still cranking out great albums, embracing middle age and then old age as though each stage of life might be his greatest inspiration. Even when his career floundered, his eccentricity and his generosity never wavered. Without ever sounding glib, Prine faced the worst of humanity with humor. There was always a clever turn of phrase in his songs or a wry observation to dispel any pathos, whether he was singing about lovers parting (“All The Best”) or a brutal murder (“Lake Marie”).

After taking most of the late 1980s off, he enjoyed a modest renaissance in the 1990s, thanks to his album The Missing Years in 1991 and the excellent (but currently out-of-print) compilation Great Days in 1993. His amiable midwestern twang made him a hero to alt-country artists during that decade and to roots artists during the next. Sidelined by medical issues, he didn’t write as many songs but kept recording and touring and releasing a string of excellent concert and covers albums that revealed him to be an imaginative interpreter. The best of them might be 1999’s In Spite Of Ourselves, on which he turned old country standards into duets with Lucinda Williams, Emmylou Harris, Trisha Yearwood, and other female singers. He seemed to get a good chuckle out of sharing these songs with these other singers, who bring out a tenderness and directness in his performances.

Two years ago, Prine released his first album of new material in over a decade, and The Tree Of Forgiveness is almost impossibly good. It plays like a small miracle, not only demonstrating his influence on some of Nashville’s most celebrated artists (including Jason Isbell and Brandi Carlile) but flaunting his eccentricities in the face of eternity. He cracks geezer jokes on the spry “Egg & Daughter Nite (Lincoln, Nebraska, 1967),” ponders the wonder of true love on “I Have Met My Love Today,” and empathizes with the statue of Vulcan that stands over Birmingham, Alabama, on “The Lonesome Friends Of Science.” It’s an album that confronts mortality but remains fearless. In fact, the nearness of heaven only made Prine find even greater significance in the small moments of life, as if to suggest that we’re all blessed just to be alive.

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Prine left behind a large and remarkable body of work: hundreds of songs that skirt the boundaries of country, folk, rock, blues, even rockabilly. Rather than a definitive collection of his greatest hits or most popular tunes, here’s a baker’s dozen of some of his lesser-known works.

“Quiet Man” (John Prine, 1971)

Prine’s first album is widely regarded as one of the finest debuts ever released, with nearly every song considered a classic. But one that’s often overlooked is this ode to the sublime, with Prine doing a high-wire act by rhyming “oodles of light” with “both of God’s eyes are shining tonight.”

“Christmas In Prison” (Sweet Revenge, 1973)

Loneliness and longing get the cinematic treatment on this country waltz about being in jail and missing someone on the outside. It might have been merely a joke, especially with Prine talking about bad food and guns carved out of soap, but as much as he relishes those details, he appreciates the idea of prison as something like a universal condition.

“He Was In Heaven Before He Died” (Common Sense, 1975)

This tune, inspired by the death of his father, contains one of Prine’s best opening lines: “There’s a rainbow of babies draped over the graveyard.” He might have written it as a dare to himself. As he wrote in the Great Days liner notes: “Where do you go from there? I consider that a challenge, though, to paint myself into a corner and then get out. I figured out that what you’re trying to do as a writer is go to places that aren’t so comfortable, that you don’t already know how to get out of.”

“Bruised Orange (Chain Of Sorrow)” (Bruised Orange, 1978)

Prine based the title track of his 1978 album on his experiences as a church janitor. One day an altar boy was killed on his way to mass, a tragedy that allows him to ponder the nature of God, to warn against bitterness, and to close with an ecstatic saxophone solo that sounds like a soul ascending to heaven.

“Down By The Side Of The Road” (Pink Cadillac, 1979)

Prine went down to Memphis to record Pink Cadillac, which features production work by Sam Phillips and his sons Jerry and Knox. On this standout, he follows a woman at loose ends, filling in enough details for a short story — including her tattoo that reads, “God-damn, my socks are still hard.” What that means is anybody’s guess, but it lends the woman a particularity, as though you might even know her.

“Unwed Fathers” (Aimless Love, 1984)

Prine’s first album on his Oh Boy label includes this sad waltz co-written with legendary Nashville songwriter Bobby Braddock, who’d penned hits for Tammy Wynette, George Jones, and Tanya Tucker. He also invited his wife at the time, Rachel Peer Prine, to take a verse, which means this song became the template for his Grammy-winning duets album In Spite Of Ourselves.

“Let’s Talk Dirty In Hawaiian” (German Afternoons, 1986)

Pretty sure “Lay your coconut on my tiki” is English.

“It’s A Big Old Goofy World (The Missing Years, 1991)

This song full of similes is a meditation on songwriting and the stubbornness it takes to pursue an idea to its fullest realization. But it also works as something as his philosophy of life: “Kiss a little baby, give the world a smile / If you take an inch, give ‘em back a mile.”

Cowboy Junkies’ “If I Were The Woman And You Were The Man” (Black Eyed Man, 1992)

Amazingly, Prine wasn’t the Toronto band’s first choice for this gender-shifting duet on their fourth album. According to guitarist/songwriter Michael Timmins, they brought in Jimmie Dale Gilmore, but the Flatlander wasn’t a good fit with frontwoman Margo Timmins’ vocals. Prine, however, immediately establishes a warm and tender dynamic with her as they trade quiet declarations of devotion. It’s one of his finest duets.

“Lake Marie” (Lost Dogs & Mixed Blessings, 1995)

A song about Native American folklore, his own crumbling marriage, and a pair of grisly murders, all tied together by one of his loveliest choruses: “We were standing, standing by peaceful waters.”

“In Spite Of Ourselves” (In Spite Of Ourselves, 1999)

On this album of country duets, Prine meets his match with Iris Dement. Theirs is the only original on the album, allowing them to play each other’s better/lesser halfs, and Prine even gives her the best lines (“Ain’t got laid in a month of Sundays / Caught him once, he was sniffin’ my undies”), but the beautiful, hilarious punchline is that they were made for each other.

“Some Humans Ain’t Human” (Fair & Square, 2005)

Prine rarely got political in his songs, but “Some Humans Ain’t Human” takes our 43rd president to task for starting a war in Iraq. He deliver that chorus—“Some humans ain’t human, some people ain’t kind”—like he’s giving you bad news. Sadly, the song remains even more relevant today, when the anti-Prine is alive and the leader of the free world.

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

On the final song on his final album, Prine presents a vision of heaven that is beautiful in its weird pleasures: He wants to drink an endless cocktail, smoke a cigarette that’s nine miles long, and cut a rug with all those beloved family members who got here before he did. Rather than a lament, he stages it like a raucous party, a celebratory homecoming, and we’re all invited.

Listen to these essential John Prine deep cuts as a playlist at Spotify or below.