John Prine, an esteemed country-folk singer-songwriter whose mordant wit camouflaged the profound seriousness of his work, has died at 73. The cause was complications from COVID-19, his spokesperson said.

Like America’s greatest country writers, Prine had a genius for putting difficult truths and complex emotions into simple language, communicating great wisdom with a conversational ease. He favored character-based portraits, capturing the dreams and delusions of everyone from the emotionally detached but fiercely sexual partners in “Donald and Lydia,” to the heroin-addicted Vietnam vet in “Sam Stone,” to the dead guy who tells the angels where he wants each of his body parts to go in “Please Don’t Bury Me.” “Give my stomach to Milwaukee/if they run out of beer,” he sang in “Bury Me.” “The blind can have my eyes/and the deaf can take both of my ears/if they don’t mind the size.”

Some of Prine’s finest pieces doubled as protest songs, like “Paradise,” which begins as a warm memory of a place from the songwriter’s youth (Paradise, KY.) before turning into a howl against the ravages of the coal industry. Other songs offered barbed satires, like “Your Flag Won’t Get You Into Heaven No More,” which sent up the hypocrisy of unthinking patriots who claimed righteousness while supporting the battles in Vietnam. “Your flag won’t get you into heaven anymore/they’re overcrowded from your dirty little war,” he sang. “Now Jesus don’t like killin’/no matter what the reason for.”

When he was still in his early twenties, Prine developed a keen ear for the inner pain of older people, a talent which resulted in two of his best-known songs. “Hello in There,” which has been recorded by everyone from Bette Midler to Joan Baez to Kris Kristofferson, tells the story of an aging couple in stark detail, before elevating to a chorus that poignantly declares “old trees just grow stronger/and old rivers grow wilder ev’ry day/old people just grow lonesome/waiting for someone to say, ‘hello in there, hello.”

“Angel from Montgomery,” made famous by a ravishing, 1974 cover by Bonnie Raitt, peered into the life of a middle-aged woman who watches “the years flow by like a broken-down dam.” In a 2000 interview with Performing Songwriter magazine, Raitt said the song “has all the different shadings of love and regret and longing. It’s a perfect expression from a genius.”

In a 2009 interview, Bob Dylan called Prine’s writing “pure Proustian existentialism,” while Roger Waters told Word Magazine in 2008 that the songwriter belonged in a category with Neil Young and John Lennon. When Prine won a Pen Award for his writing, John Mellencamp introduced him by referencing his song “Jesus, The Missing Years,” which speculates on the activities of Christ during the 18 years not covered in the Bible. “Who writes songs like that?” Mellencamp asked. “God and John Prine.”

Rolling Stone magazine called him “the Mark Twain of American Songwriting.”

Over a 50-year career, Prine’s songs have been covered by hundreds of artists, from Johnny Cash and John Fogerty to Miranda Lambert and R.E.M. Prine’s own recordings, delivered in a brazenly nasal twang, tended to be dry and unfussy, with a sound as blunt, and deceptively plain, as his language.

Image zoom Tony Russell/Redferns

John Prine was born on Oct. 10th, 1946 in Maywood, Illinois, to William Prine, a tool-and-die maker and Verna Hamm, a homemaker. He began to learn the guitar at 14, schooled in the instrument by his brother, David. After graduating from high school, he was drafted into the Army during Vietnam, though he was stationed in Germany where he saw no action.

Upon returning to Chicago, he held a job as a mailman while, by night, he performed at the local club the Fifth Peg. He soon became a fixture in the city’s rich folk scene, earning up to $1000 a week with his music. At one show at Earl of Old Town, he was seen by the film critic Roger Ebert, who raved about his work in a review in the Chicago Sun-Times under the headline: “Singing Mailman Delivers a Powerful Message in a Few Words.” Another key folkie on the scene, Steve Goodman brought Kris Kristofferson to a Prine show and, “by the end of the first line, we knew we were hearing something else,” Kristofferson recalled to Rolling Stone in 2017. “It must have been like stumbling unto Dylan when he first busted into the Village scene.”

Kristofferson arranged a showcase for Prine at New York’s Bitter End, which inspired Atlantic Records’ president Jerry Wexler to sign him to the label. His self-titled debut, which appeared in 1971, opened with a song “Illegal Smile” that became an anthem for defiant pot heads. “Fortunately, I have the key to escape reality,” sang the song’s depressed narrator. “And you may see me tonight with an illegal smile/it don’t cost very much, but it lasts a long while.”

Prine asserted that the song wasn’t about drugs but, instead, referred to his ability to escape through the power of subversive humor. Though his debut also included “Hello in There” and “Angel from Montgomery,” it didn’t sell well. But, it did earn Prine plaudits from his peers and a Grammy nomination for Best New Artist. His follow-up, Diamonds in the Rough, released in 1972, underscored his eagerness to break with convention by its raw production style, though Prine subsequently found a somewhat friendlier sound for albums like Sweet Revenge in ’73 and Common Sense two years later. Over the years, Prine continued to finely weigh humor and wisdom in his songs, evidenced by “Dear Abby,” where he assumed the voice of the famous advice columnist. He curtly dismissed every letter writer with the refrain: “You have no complaint/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.”

After cutting seven albums for major labels — first for Atlantic and then for Asylum Records — Prine formed his own record company, Oh Boy, making him a D.I.Y. pioneer. In 1991, he won his first Grammy, for Best Contemporary Folk Album, for The Missing Years. But by ’98, he began to experience serious health issues. After being diagnosed with squamous cell cancer, he had surgery that involved removing part of his neck, a procedure that damaged some nerves in his tongue. The result added even more gravel to an already rough-hewn voice.

In 2001, Prine enjoyed an acting role in the movie Daddy & Them, directed by Billy Bob Thornton. Four years later, he won his second Grammy for Best Contemporary Folk Album, for Fair & Square. In 2013, the songwriter was diagnosed with lung cancer and had his left lung removed. Regardless, he was back on tour six months later.

Two years ago, Prine released his first album of original material in over a decade, The Tree of Forgiveness, supported by guest appearances from star admirers like the Black Keys’ Dan Auerbach, Jason Isbell, and Brandi Carlile. It became the highest charting album of his career, opening at No. 5 on the Billboard 200. In 2020, he won the Grammy Lifetime Achievement Award.

In the last song on Prine’s final album, he imagined what it would be like “When I Get to Heaven.” He envisioned it as a great place to “get a cocktail; vodka and ginger ale,” “smoke a cigarette that’s nine miles long,” and “kiss a pretty girl on the tilt-a-whirl.”

At the same time, he expected to see his cousin Jackie “still cutting up a rug,” as well as his mama and her sisters, because, he noted “that’s where all the love starts.”

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