Spend time with any of John Prine’s 18 albums (the first seven are newly remastered and reissued for the box set Crooked Piece of Time: The Atlantic & Asylum Albums (1971-1980); his subsequent output was released on his own independent label, Oh Boy) and it becomes abundantly clear that his songs don’t fit neatly into the usual categories—love songs, happy songs, sad songs—because often they are all those things at once. Smiles and tears can be evoked by the same song. Tender, funny, heartbreaking, wise—most suggest the deeper truths that lay beneath their delightfully specific details and carefully chosen phrases. Many are populated with indelible characters, all set to singalong, anthemic melodies that become unforgettable—forever stuck in your head after a single hearing. Stricken with throat cancer at the age of 52 after years of heavy smoking, John Prine fought back, finding ways to use his diminished voice to add new poignance and expressiveness to the many classics of his songwriting catalog. Never a portentous, epic chronicler in the mold of Dylan, Prine is an everyman’s sage, expert at sly, silly, short statements that ring true and hopefully will never be forgotten. Here are a dozen songs—because we just couldn’t limit ourselves to 10—that are evidence of Prine’s spirit and mastery.

"Illegal Smile," "Sam Stone," and "Paradise" from John Prine (1971, Atlantic)

Meaningful art is made by artists with something to say, a belief or observation to add to the cosmic conversation, epiphanies that literally have to be expressed. Rarely has that been truer than in the release of John Prine, the singer-songwriter's debut album. Call it vision, pent up creativity or just plain luck, but few artistic debuts have ever been blessed with as many genuinely iconic songs. Recorded in Memphis at American Sound Studio—except for "Paradise" which was tracked in NYC—the sound of the album was raw and immediate with able assistance from "The Memphis Boys," the house band that included guitarist Reggie Young, pianist Bobby Wood, drummer Gene Chrisman and organist Bobby Emmons. As for the young songwriter's musical talents (Prine was not yet 25), he's a passable acoustic rhythm guitarist. His voice, much like that of another noted storyteller—think Bobby Zimmerman—is an acquired taste, particularly later in his career after surviving cancer.

As a career opener, few are more fun or naughtier than "Illegal Smile," which extols the liberation of being high on pot. The self-deprecating persona Prine would create and inhabit—his signature mix of detailing life's troubles and his own foibles but accepting it all with humor and the faith that all would somehow work out—begins in this first song. His bankroll is thin. The bottom is the only place he's ever been. And he's chased a rainbow down a dead-end street. And yet the song turns and ends with one of Prine's life defining statements: "Won't you please tell the man I didn't kill anyone/ No, I'm just trying to have me some fun."

Easily the saddest song he ever wrote, the exquisitely desolate "Sam Stone," with its deft lyrics and heart-wrenching tale of the downward spiral of a Vietnam Vet turned junkie highlights Prine's lyrical skills for the first time. In Sam's death scene where he's "climbing walls while sitting in a chair/ … While the room smelled just like death/ With an overdose hovering in the air," Sam's harrowing demise is depicted with breathtaking wordplay:

"But life had lost its 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."

A lifelong lover of bluegrass and classic country music, this son of Kentuckians who was raised in the Maywood section of metropolitan Chicago, early on penned what has since become a forcefully strummed bluegrass standard. In "Paradise" Prine remembers family trips to Kentucky, a world where again the sense of smell was prominent, ("The air smelled like snakes") and eloquently details his stand on man's greed and shortsightedness in stark terms: "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."

"Angel from Montgomery" from John Prine Live (1988, Oh Boy)

From the first album but heard here in a live version with Bonnie Raitt is what ranks as Prine's most famous tune, "Angel from Montgomery." Originally recorded solo with an unusually rough vocal take, this quixotic tale found its greatest success as a duet. Written from a woman's point of view, Prine mixes his healthy appreciation for history and especially, the power of nostalgia, with a simple relatable question about empty souls: "How the hell can a person go to work in the morning/ And come home in the evening and have nothing to say?" and an even simpler plea: "Just give me one thing that I can hold on to/ To believe in this living is just a hard way to go." One of Prine's most famous characters, "Angel," is vividly conjured in these two lines: "When I was a young girl well, I had me a cowboy/ He weren't much to look at, just a free rambling man."

Bonnie Raitt & John Prine - Angel From Montgomery (Live at Farm Aid 1986)

Farm Aid

"Egg & Daughter Nite, Lincoln Nebraska 1967 (Crazy Bone)" and "When I Get to Heaven" from The Tree of Forgiveness (2018, Oh Boy)

Forty-nine years, three marriages, two near fatal bouts with cancer and many, many original songs after his debut recording, Prine wound up his career with an album filled with many of the same joys, reflections and levity that he began his career writing about, though perhaps this time with more of an eye towards eternity. Listening now, after his passing, it's clear that in many ways he was the same man—deeper in voice, battered by life, deeply aware of the sadness and hardships inherent in the human condition and yet still in love with laughter and unable to stay serious for long. Prine's last batch of originals, while not his best, still has more heart and songcraft than most of his competitors' best. "Egg & Daughter Nite" comes from a story Prine heard about farmers dropping their eligible teenage daughters at the local roller rink before setting up in Lincoln, Nebraska, to sell eggs. He revels in the chorus tag "crazy bones" delivered in his signature sing/talk, works in a flavorful but rhyme-averse word like "Brylcreem," and has an audibly good time throughout. Now prophetic in the extreme, the album's closer, "When I Get to Heaven," another of his wry fantasies, opens with a harp flourish and spoken word intro, before launching into a joyous chorus romp where he has "a cocktail—vodka and ginger ale," puffs on "a cigarette that's nine miles long" and even sets out to charm critics, "those syph'litic parasitics." Ouch! In the chorus' final line, his exuberance for life—despite its many hardships—comes roaring back once more with obvious relish: "this old man is goin' to town."

"Grandpa was a Carpenter" from Sweet Revenge (1973, Atlantic)

Without guile or artifice, Prine was able to use his own autobiography to fashion flavorful, detailed vignettes like this one from the album that also contains "Dear Abby," his goofy and much beloved, salute to the advice columnist. Even though "Grandpa" is about his grandfather who was "level on the level," "voted for Eisenhower because Lincoln won the war," and like his grandson, "chain-smoked Camel cigarettes," it's his grandmother who turns out to be the more finely drawn portrait:

"Now my grandma was a teacher

Went to school in Bowling Green

Traded in a milking cow

For a Singer sewing machine."

While Prine had a number of sturdy songwriting modes and tempos that he often fell back on to carry his finely wrought parables, when the easy-to-relate-to melodic turns melded with his meticulously consequential words, masterpieces like "Grandpa" were born.

"The Great Compromise" from Diamonds in the Rough (1972, Atlantic)

As simple and relatable as Prine could be in his storytelling, and as "aw shucks" as he seemed in person, he was also a perceptive philosopher. In the pointed Vietnam War protest number, "The Great Compromise," he's an artist determined to hold onto his principles, who faces an unfaithful lover and an untruthful government, but is betrayed and bitterly disillusioned by both. The rising verses followed by descending choruses track the tune's emotional journey. The chorus lines leave no doubt about where the singer's loyalties started out and the harsh realizations he has come to believe in. "I used to sleep at the foot of old glory/ And awake in the dawn's early light/ But much to my surprise when I opened my eyes/ I was a victim of the great compromise."

"The Oldest Baby in the World" from Aimless Love (1984, Oh Boy)

Fed up with the machinations of the music business, anxious to take control of his own music and career, Prine and his manager, the late Al Bunetta, formed Oh Boy Records in Nashville in the early 1980s. The first album, recorded when money was tight, was Aimless Love, which was also his first collection of new material in four years. Not surprisingly given that length of time, there were some gems in this collection, headlined by yet another amusing yet slightly sad tale, this one co-written with the great and sadly late Donnie Fritts. Set to a slow tempo with a steel guitar crying in the background, this is an affectionate musing on an older woman who "would if she could/ And she should but nobody will," and who still holds out hope for love with Prine generously recognizing that "youth is a costume/ And the beauty within lies unfurled."

"The Sins of Memphisto" from The Missing Years (1991, Oh Boy)

Timing, often the key to life, is also the principle behind the success of 1991's The Missing Years. After five years of silence, Prine and manager Al Bunetta decided that a band record would be a healthy change, and along with producer Howie Epstein collected an all-star group including Albert Lee, Mike Campbell, Tom Petty, Phil Everly, Bonnie Raitt, Bruce Springsteen, all of whom had by then come to respect Prine's incredible body of songwriting. As far as recognition among your peers goes, this is the pinnacle of Prine's career. Happily, he had a batch of new songs—single efforts and co-writes—strong enough to showcase all this instrumental firepower and in the end win him his first Grammy Award. The sound is the most produced of Prine's career, with a more aggressive mix and larger overall sonic image. Mischievous is a word that has long been applied to the image of Prine that emerges from his songs. Here he begins with the chorus—a new device he was enamored with at that point in his career—before talking his way through verses which when read on a page are more of a word jumble than a coherent story. Listen closely and it slowly begins to sink in that instead of any grandiose voodoo yarn about making the same mistakes over and over again, this is just Prine having fun—a conclusion supported by Esmeralda's post-coital whispering in the Hunchback's ear, "Exactly-odo, Quasimodo."

"Lake Marie" from Lost Dogs + Mixed Blessings (1995, Oh Boy)

Among Prine aficionados there will always be a debate over whether Prine was better solo or fronting a band and here on the second of the early 1990s albums produced by Tom Petty's bassist Howie Epstein a convincing case was made for collaborators. With a large all-star ensemble that included Epstein, another Heartbreaker—keyboardist Benmont Tench, string virtuoso John Jorgenson, Marianne Faithful on background vocals and many more, Prine cut another strong band album headlined by this impassioned tale that like so many Prine originals mixes very specific autobiography, in this case a failing marriage, with the naming story of two lakes in Northern Illinois, but adds as a twist a double murder in a forest preserve. As incongruous as that all sounds, it works, thanks to a lilting, repeated chorus hook of "Standing by peaceful waters/ Whoa wah oh wah oh." When stuck for words Prine could always come up with a wordless interpolation to save the day. The song—with Prine talking the verses and singing the choruses—wrapped with this stanza:

"You know what blood looks like in a black and white video?

Shadows. Shadows! That's what it looks like

All the love we shared between her and me was slammed

Slammed up against the banks of old Lake Marie; Marie."

As impressionistic, draw-your-own-conclusion endings go, this is a masterful mingling.

John Prine on Austin City Limits "Lake Marie"


"In Spite of Ourselves" from In Spite of Ourselves (1999, Oh Boy)

Miraculously, neck and throat cancer did not take away John Prine’s voice though it did lower its range, steal away much of its former elasticity, and add a coarse tone that the canny singer-songwriter immediately learned to use to add extra gravity to many of the treasures in his catalog. To offset these rough vocal edges, he wisely recorded a pair of duet albums with female singers, one focused on country music classics—For Better, or Worse—and his first release after surgery and radiation In Spite of Ourselves recorded before, during and after surgery. Not surprisingly, Prine’s idiosyncratic voice was simpatico with another singer whose warbling can also be an acquired taste: Iris DeMent. Here Prine pulls out the stops on his gifts for the high/low art of rhyming such, uh, common pursuits as « sniffin’ undies, » « drinking beer like oxygen » and being a « wacked out weirdo and a love bug junkie. » There probably isn’t a better example of why Prine has fans of all ages, genders, education and income brackets than this hilarious and ultimately very endearing love story.