I was 17 when I first met John Prine. I had heard his eponymous debut album three years prior, an album that was already 15 years old. I confused the audience that hot summer night at Riverfest in La Crosse, Wisconsin. What was this spiky-haired skateboarding punk doing front and center, singing along to every word? I was an alien in a sea of nostalgic hippies and stoner middle-aged bikers. I was enthralled.
After the last round of applause, Prine laid his guitar in its case and carried it off the stage to the small Airstream trailer that was acting as the green room for the night. Most everyone had gone but me when he stepped out with a lit cigarette and a can of Old Style.
"What are you doing here, kid?" he lobbed at me suspiciously.
"I just wanted to say thank you for the music."
"How old are you?"
"Damn, my first album came out before you were born. You sure know how to make a man feel old."
That was the summer of 1989, and I had just met John Prine.
In 1971, the United States was stumbling, feeling political, economic and cultural malaise. There was a need for a voice to speak plainly about the regrets of a nation that suddenly found it was losing direction. Out of that need, or perhaps more precisely out from that need, came the voice of John Prine.
Prine's 1971 debut on Atlantic Records caught fire the same way a damp bale of hay does, slowly heating from the inside of the singer-songwriter community of Chicago until it spontaneously combusted into the larger listening audience's consciousness as a burning bush of unmitigated truth. The album cover, featuring Prine dressed in denim and seated on hay bales, accurately depicted the workmanlike songs inside. Instant classics like "Illegal Smile," "Hello in There" and "Angel From Montgomery" bristled with a deep melancholy and a pristine storyteller's phrasing, but it was the track "Sam Stone" that ultimately sparked the prairie fire.
The story of a Vietnam vet whose postwar trauma drove him to heroin addiction was an all too common story in '70s America, causing Kris Kristofferson to famously quip, "He writes songs so good we will have to break his thumbs."
Embraced early by the elder statesmen of folk and country, Prine enjoyed almost immediate legend status when Bob Dylan appeared with him – accompanying on harmonica – during a gig in New York. The Father of Bluegrass, Bill Monroe, famously remarked that when he heard Prine's "Paradise" he thought it was one of his own that he had forgotten.
Covers of his songs soon followed, by the likes of the aforementioned Kristofferson, Johnny Cash and Bonnie Raitt. Prine solidified his place within the singer-songwriter pantheon when his sophomore 1972 album Diamonds in the Rough garnered him a best new artist Grammy nomination. Containing the tender nostalgia of "Souvenirs" and the subtle political commentary of "The Great Compromise," Prine also begins to flash his well-known humor in the song "Yes I Guess They Oughta Name a Drink After You." Prine recorded two more albums for Atlantic, 1973's Sweet Revenge and 1975's Common Sense, culminating in the 1978 greatest hits collection Prime Prine. Most artists would be content to have rested there.
Prine moved to Asylum Records for his next three records. 1978's Bruised Orange is often cited as Prine's artistic peak, displaying a broader range of style, moving from the more traditional country and folk to a more West Coast seriousness. The following year's Pink Cadillac found him shifting gears completely and embracing the early rock sounds of Nashville, and working with Sun records impresario Sam Phillips. The album is generally considered Prine's artistic nadir and stands as a counterpoint to his previous releases. Prine moved back to a more country sound for his final major label release, Storm Windows, in 1980. Low sales and the loss of focus left John Prine seemingly washed up and done as a new decade dawned.
But 1984 saw the return of Prine to recording and also wearing the hat of a record label owner. Initially started in 1981 as a way to release new music without the obligations that come with a major label, Prine's Oh Boy imprint would be the permanent home for Prine from then on, and acted as a conduit to a secondary surge of releases, from 1984's Aimless Love on through The Missing Years in 1991. He worked the regional circuits, returning to the club dates and folk circles of his early years.
Working alongside a new batch of artists like Greg Brown, Steve Earle, James McMurtry and Iris DeMent, he cemented his place as a master statesman of independent singer-songwriters, working at a level of status and fame that afforded him the autonomy and freedom to explore, collaborate and organically grow as a musician. In 1992, he won a Grammy for The Missing Years. It signaled the return of John Prine to the national stage.
In 2005, Prine was the first singer-songwriter to perform at the Library of Congress, leading to an extended interview about his songwriting and how that relates to poetry with then-U.S. Poet Laureate Ted Kooser.
These days, Prine continues to write, record and perform after two bouts with cancer and three marriages, finally releasing his most recent album, Tree of Forgiveness, in 2018. It would be difficult to overestimate the influence and reach John Prine has had on folk and country music over the past 50 years. Just listen to the albums mentioned here and imagine for yourself, or see the great man do it live at the ornate Bob Carr this week.
– This story appears in the Dec. 4, 2019, print issue of Orlando Weekly. Get our top picks for the best events in Orlando with our weekly Events newsletter.