When John Prine began his career in 1969, he was a 23 year-old mailman just home from a stint in the army as a mechanic in West Germany. After he moved back to his suburban Chicago hometown of Maywood, Illinois, he began writing simple three-chord folk songs about lonesome elderly couples (“Hello in There”), morphine-addicted veterans (“Sam Stone”), and the strip mining that destroyed his father’s Kentucky hometown (“Paradise”). Prine began playing open mics in Chicago folk clubs like the Fifth Peg and the Earl of Old Town, eventually earning a weekly residency, before being discovered one night by Kris Kristofferson. Within two years of stepping on a stage, Prine released a debut album for Atlantic Records, and the plainspoken Midwesterner was being hailed as the latest in a long line of “new Dylan”s.
Prine’s stint with Atlantic, however, lasted only four years and as many studio albums. Two years after releasing his final Atlantic album, 1975’s Common Sense, Prine signed a three-album deal with the more singer-songwriter-oriented Asylum Records, which would release his late ’70s masterpiece Bruised Orange in 1978. But Prine soon realized that he was not interested in being in a relationship with any sort of traditional label.
By 1981, immediately following his three Asylum albums, he’d founded his own label, Oh Boy Records, and by 1984 he was self-releasing full-length records by mail order. That way, as Prine explained at the time to Bobby Bare on The Nashville Network, “There ain’t no middleman… no swarthy little character in Cleveland that gets the money from the people that want the music, and then… takes most of it, twirls his mustache, and sends me 12 cents.”
Since founding Oh Boy, Prine has released a total of 14 albums, including some of the most renowned of his career: From his 1991 comeback album The Missing Years, to his 1999 country duets collection In Spite of Ourselves, to his most recent masterpiece, 2005’s Fair & Square. Almost all of Prine’s Oh Boy discography can be found on Bandcamp.
By the time he went out on his own in the ’80s, Prine had developed enough of a dedicated following to directly support his music—primarily, by buying tickets to his regularly sold-out theater shows around the country—without the financial backing of a label. As Prine put it in 1995, “I just didn’t want to continue recording unless it was in a manner that seemed to make more sense to what I actually did, which was pack my suitcase and go on the road for a living.”
Although Prine is still best known for the modern-day country-folk standards on his debut 1971 self-titled album, the latter half of his career is populated with exemplary moments of song craftsmanship every bit as moving and profound as “Angel From Montgomery” or “Sam Stone.”
Here are eight highlights from Prine’s Oh Boy collection.