John Prine was an Army veteran walking a U.S. Postal Service beat in Chicago and writing songs on the side when Kris Kristofferson, among others, heard him and spread the word about Prine’s gifts. Pretty soon, he resigned as a letter carrier; his supervisor snickered, “You’ll be back.” In January, he was given a lifetime achievement Grammy for his contributions to songwriting. The singing letter carrier almost always had the last laugh.
Prine, who died on Tuesday from complications of Covid-19, was one of music’s legitimately unique musicians. He took familiar blues themes — my baby left me — but filled them with whimsy and kindness. He liked a saucy lyric, and wrote movingly, in character, of the quiet lives and loneliness of humdrum people. He seemed like a Zen sage and offered an uncynical live-and-let-live morality in his songs, writing in a colloquial voice that showed a love of the way Americans speak. He showed how much humor you could put in a song, and still be taken seriously. He had less in common with any other songwriter than he did with Mark Twain.
He grew up in Maywood, a western suburb of Chicago, to working-class parents from Kentucky, where he often spent summers with relatives and fell in love with country music and bluegrass. By 13, he was performing in rural jamborees. When he debuted in 1971, in his mid-twenties, he sounded like an old man already, so years later, when he got old and went through two cancer treatments, he still sounded like himself. From his first to his last, he wrote songs that were tender, hilarious, and wise, without grandstanding any of these traits. Here are 15 of the best.
‘Angel From Montgomery’ (1971)
“Angel From Montgomery,” his best-known song, begins with a little declarative startle: “I am an old woman, named after my mother.” It’s an incisive and terrifying look at the dissatisfactions of a bad marriage and a woman’s sense of being economically trapped in her misery. Bonnie Raitt recorded it three years later, and masterfully uncovered some of the song’s dormant melodies.
‘Your Flag Decal Won’t Get You Into Heaven Anymore’ (1971)
Prine’s self-titled 1971 debut album is a playlist all its own; it has more great songs than a lot of respected songwriters have in their entire careers. The moral stance of this sprightly folk-rock ditty is a response to what he saw as sham patriotism during the Nixon years, and it remains relevant: “Jesus don’t like killing/No matter what the reason’s for.” Prine, a former altar boy, stopped playing it live for a number of years, but when George W. Bush became president, Prine said, “I thought I’d bring it back.”
‘Hello in There’ (1971)
Some fans and critics are put off by this song and its slightly lesser companion, “Sam Stone,” which they see as performative displays of sensitivity toward the vulnerable, or what we now call virtue signaling. Yet somehow, we don’t ever criticize singers for signaling vices and meanness. Prine sings in the voice of an old married man with a dead son, who spends his days in silence and loneliness, and who at the end of the song, asks people to be kind to the elderly.
‘The Frying Pan’ (1972)
For his second album, “Diamonds in the Rough,” Prine assembled a small, mostly acoustic band and pursued a front-porch, Appalachian simplicity. Like a lot of his songs, this one takes a lighthearted view of domestic complications: a man comes home and discovers his wife has run off with a traveling salesman. He cries miserably, recounts what he loved about her (“I miss the way she used to yell at me/The way she used to cuss and moan”), and full of pride, comes to the wrong conclusion: Never leave your wife at home.
‘Please Don’t Bury Me’ (1973)
For people who love Prine’s music, there’s some small solace in listening to his songs about death, which have the same sense of mischief and acceptance as the ones about broken marriages. (Try “Mexican Home” or “He Was in Heaven Before He Died.”) The narrator is dead, and as angels explain to him how it happened, they also recap his last wish: to not be dropped into a cold grave, but to be put to practical use, as an organ donor: “I’d druther have ‘em cut me up/And pass me all around.” A kind of recycling anthem from his terrific third album, “Sweet Revenge.”
‘You Never Can Tell’ (1975)
Almost like an apology, Prine concludes “Sweet Revenge,” a grieving, downhearted album, with an exuberant Chuck Berry cover, one great writer nodding to another. The Memphis R&B guitarist Steve Cropper produced the record and put together a crack horn section, which pushes ahead of some barrelhouse piano. Prine wasn’t a rocker, but he could rock.
‘That’s the Way the World Goes Round’ (1978)
Prine seemed to have an unlimited ability to expand and vary songwriting structures and perspectives. This track, which has been covered by Miranda Lambert and Norah Jones, has two verses: In the first, the narrator describes a drunk who beats his old lady, and in the second, the narrator gets stuck in a frozen bathtub (it’s hard to explain) and imagines the worst until a sudden sun thaws him out. Both verses illustrate the refrain: that’s the way the world goes ’round. Even when circumstances are bad in Prine songs, he favors optimism and acceptance.
‘Iron Ore Betty’ (1978)
A lot of Prine songs celebrate physical pleasure: food, dancing and sex, which he gallantly prefers to call “making love.” The working-class singer in this soulful, up-tempo shuffle feels unreserved delight at having a girlfriend (“We receive our mail in the same mailbox/And we watch the same TV”), and wants us to know he and Betty aren’t just friends (“I got rug burns on my elbows/She’s got ‘em on her knees”). OK guy, we get it.
‘Just Wanna Be With You’ (1980)
A stomping number from “Storm Windows” in the style of Chuck Berry, with the Rolling Stones sideman Wayne Perkins on guitar. Prine’s lyrics don’t distinguish between reality and absurdity — they don’t clash, they mix — and here’s one more way to say you’re happy and in love: “I don’t even care what kind of gum I chew.” And another one more: “Lonely won’t be lonesome when we get through.”
‘Let’s Talk Dirty in Hawaiian’ (1986)
Prine had a sideline in novelty songs, which give full voice to his comic absurdity, throwaways that are worth saving, including the 1973 semi-hit “Dear Abby,” “Big Old Goofy World,” and this now-problematic number from “German Afternoons” inspired by a paperback book called “Instant Hawaiian.” Prine and his co-writer Fred Koller began making up Hawaiian-sounding nonsense words full of sexual innuendo, and Lloyd Green added airport-Tiki-bar bar steel guitar for maximum faux authenticity. You can say Prine’s loving disposition makes the song OK, and you can also say it doesn’t.
‘All the Best’ (1991)
After five years away, Prine returned with “The Missing Years,” a Grammy-winning album produced by Howie Epstein, Tom Petty’s bass player. The singer in this gentle, masterful miniature claims to want good things for an ex-lover, but feelings aren’t simple: “I wish you don’t do like I do/And never fall in love with someone like you” twists the knife. Now recording for his own label, Oh Boy Records, Prine was about to hit a hot streak.
‘Lake Marie’ (1995)
Bob Dylan, who was a huge fan, called the haunted, mysterious “Lake Marie” his favorite Prine song, and who are we to disagree with Dylan on the topic of songwriting? Even though Epstein’s booming production draws too much attention to itself, “Lost Dogs + Mixed Blessings” is full of winners: the simple, loving ballad “Day is Done,” the rapid-fire doggerel of “We Are the Lonely,” and the calm, ornery “Quit Hollerin’ at Me,” where Prine tells his wife that the neighbors “already think my name is ‘Where in the hell you been?’”
‘In Spite of Ourselves’ (1999)
Prine was diagnosed with cancer, and doctors removed a tumor from the right side of his neck, which took away his already-modest ability to project his voice. But incredibly, his stolid singing was now perfect for harmonies, and he cut a duets album called “In Spite of Ourselves” with female country and Americana singers. On its one original song, Prine and Iris DeMent trade backhand compliments (“She thinks all my jokes are corny/Convict movies make her horny”) that read like a divorce complaint, but turn out to be only pillow talk.
‘Some Humans Ain’t Human’ (2005)
At seven minutes and three seconds, this track from “Fair and Square” is the longest song on any of his studio albums. A cloud of slide guitar keeps this soft waltz afloat and allows Prine to express his disapproval of, if not contempt for, so-called humans who lack empathy for others. There’s a couplet that is clearly about George W. Bush, and Prine noticed that some audience members were surprised by it. “I never tried to rub it in anybody’s face, but I thought it was pretty clear that I wasn’t closet Republican,” he told the Houston Press.
‘When I Get to Heaven’ (2018)
In 2013, doctors removed the cancerous part of Prine’s left lung, which sidelined and weakened him. It’s hard now to listen to his final album, “The Tree of Forgiveness,” which was nominated for three Grammys, and not think Prine heard the clock ticking louder. There’s so much tenderness in “Knockin’ on Your Screen Door,” about a man whose family left him with only an 8-track tape of George Jones, and in the elegiac, reassuring parental entreaty “Summer’s End.” In the last song, “When I Get to Heaven,” Prine describes his ideal afterlife: a rock band, a cushy hotel, a girl, a cocktail (“vodka and ginger ale”) and “a cigarette that’s nine miles long.” He removes his watch, and asks, “What are you gonna do with time after you’ve bought the farm.”