One of the most celebrated singer/songwriters of his generation, John Prine was a master storyteller whose work was often witty and always heartfelt, frequently offering a sly but sincere reflection of his Midwestern roots, writing about the lives of ordinary people in a remarkable and perceptive way. While Prine's songs were most often rooted in folk and country flavors, he was no stranger to rock & roll, R&B, and rockabilly, and could readily adapt his rough but expressive voice to his musical surroundings. Prine never scored a major hit of his own, but his songs were recorded by a long list of well-respected artists, many of them celebrated songwriters themselves, including Johnny Cash, Bonnie Raitt, Kris Kristofferson, George Strait, Bette Midler, Paul Westerberg, and Dwight Yoakam. Prine's self-titled debut album, released in 1971, was widely regarded as an instant classic and featured some his best-known songs, including "Sam Stone," "Hello in There," "Paradise," and "Illegal Smile," while 1972's Diamonds in the Rough was considered nearly as strong. 1978's Bruised Orange was a low-key return to the tone of his debut, and 1979's Pink Cadillac was a tribute to his love of rockabilly and first-generation rock & roll. In the 1980s, Prine broke away from the major labels to form his own label, Oh Boy Records, and working at his own pace and following his own inclinations, he produced a handful of fine and idiosyncratic albums, including 1991's The Missing Years, the 1999 duets collection In Spite of Ourselves, and 2018's graceful finale The Tree of Forgiveness.

John Prine was born October 10, 1946, in Maywood, Illinois. Raised by parents firmly rooted in their rural Kentucky background, at age 14 Prine began learning to play the guitar from his older brother while taking inspiration from his grandfather, who had played with Merle Travis. After a two-year tenure in the U.S. Army, Prine returned to Illinois and became a fixture on the Chicago folk music scene in the late '60s, befriending another young performer named Steve Goodman while holding down a day job as a mailman. Prine earned his first press coverage of note in 1970 when film critic Roger Ebert stopped into a bar where Prine was playing in search of a beer after attending a screening and was captivated by Prine's performance. When Goodman found himself opening for Kris Kristofferson, he urged the songwriter to check out his friend Prine. Kristofferson recognized their talent, and when they visited New York City a few months later, Kristofferson allowed the two Chicagoans to play three songs each at one of his shows. An executive from Atlantic Records was in the audience, who offered Prine a recording contract the next day.

In 1971, Prine went to Memphis to record his eponymously titled debut album; though not a commercial success, critics praised the LP, and songs like "Sam Stone" (the harsh but compassionate tale of a drug-addled Vietnam veteran) and "Hello in There" (a first-person meditation on old age) were singled out for particular praise. Neither 1972's Diamonds in the Rough nor 1973's Sweet Revenge fared any better on the charts, but Prine's work won great renown among his fellow performers; the Everly Brothers and Johnny Cash both covered his song "Paradise," while Bette Midler and Joan Baez offered renditions of "Hello in There," and Bonnie Raitt memorably interpreted "Angel from Montgomery."

For 1975's Common Sense, Prine turned to producer Steve Cropper, the highly influential house guitarist for the Stax label; while the album's sound shocked the folk community with its reliance on husky vocals and booming drums, it served notice that Prine was not an artist whose work could be pigeonholed, and was his only LP to reach the U.S. Top 100. Despite its relative success, it was his last album for Atlantic, and Steve Goodman took over the reins for 1978's folky Bruised Orange, Prine's debut for Asylum Records. With 1979's Pink Cadillac, he took another left turn and recorded an electric rockabilly workout produced at Sun Studios by the label's legendary founder Sam Phillips and his son Knox.

Following 1980's Storm Windows, Prine was dropped by Asylum, and he responded by forming his own label, Oh Boy Records, with the help of longtime manager Al Bunetta, allowing him to record without having to deal with middle men. The label's first release was 1984's Aimless Love, and under his own imprint, Prine's music thrived, as 1986's country-flavored German Afternoons earned a Grammy nomination in the Contemporary Folk category. After 1988's John Prine Live, his first concert set, he released 1991's Grammy-winning The Missing Years; co-produced by Howie Epstein of Tom Petty's Heartbreakers, the album featured guest appearances from Bruce Springsteen, Bonnie Raitt, and Tom Petty and proved to be Prine's biggest commercial success to date, selling nearly 250,000 copies. After making his film debut in 1992's John Mellencamp-directed Falling from Grace, Prine returned in 1995 with Lost Dogs and Mixed Blessings, also produced by Epstein, which earned him another Grammy nomination.

In 1998, while Prine was working on an album of male/female country duets, he was diagnosed with squamous cell carcinoma, with the cancer forming on the right side of his neck. Prine underwent surgery and radiation treatment for the cancer, and in 1999 was well enough to complete the album, which was released as In Spite of Ourselves and featured contributions from Emmylou Harris, Lucinda Williams, Trisha Yearwood, Patty Loveless, Connie Smith, and more. In 2000, Prine re-recorded 15 of his best-known songs (partly to give his voice a workout following his treatment, but primarily so Oh Boy would own recordings of his earlier hits) for an album called Souvenirs, originally issued in Germany but later released in the United States. In 2005, he issued Fair Square, a collection of new songs, followed by a concert tour. Two years later, alongside singer and guitarist Mac Wiseman, Prine released Standard Songs for Average People, a collection of the two musicians' interpretations of 14 folk and country classics. In Person On Stage, a collection of performances from various concert tours, appeared in 2010.

In 2016, Prine issued a follow-up to In Spite of Ourselves titled For Better, Or Worse, another set of duet performances of classic country tunes. This time around, Prine's vocal partners included Kacey Musgraves, Alison Krauss, Miranda Lambert, Susan Tedeschi, Lee Ann Womack, Kathy Mattea, and Prine's frequent collaborator Iris DeMent. Prine teamed up with Nashville producer Dave Cobb to record 2018's The Tree of Forgiveness, his first set of original songs since 2005; the album included guest appearances from Brandi Carlile, Jason Isbell, and Amanda Shires. The record was a critical and commercial success, rising to number five on the Top 200 albums chart, peaking at number two on the Country Albums chart, and going all the way to number one on the Folk albums chart. The Tree of Forgiveness would prove to be Prine's last hurrah; he died on April 7, 2020, from complications of the COVID-19 virus. He was 73 years old. ~ Jason Ankeny, Rovi