John Prine

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Prine's self-titled debut album was released in 1971. Kristofferson (who once remarked that Prine wrote songs so good that "we'll have to break his thumbs") invited Prine and Goodman to open for him at The Bitter End in New York City. In the audience was Jerry Wexler, who signed Prine to Atlantic Records the next day. The album included Prine's signature songs "Illegal Smile" and "Sam Stone", and songs that became folk and country standards, "Angel from Montgomery" and "Paradise." The album also featured "Hello in There", a song about aging that was later covered by numerous artists, and "Far From Me", a lonely waltz about lost love for a waitress, which Prine later said was his favorite of all his songs. The album received many positive reviews, and some hailed Prine as "the next Dylan". Bob Dylan himself appeared unannounced at one of Prine's first New York City club appearances, anonymously backing him on harmonica.

Prine's second album, Diamonds in the Rough (1972), was a surprise for many after the critical success of his first LP; it was an uncommercial, stripped-down affair that reflected Prine's fondness for bluegrass music and features songs reminiscent of Hank Williams. Highlights of the compilation include the allegorical "The Great Compromise", which includes a recitation and addresses the Vietnam War, and the ballad "Souvenirs", which Prine later recorded with Goodman.

His subsequent albums from the 1970s include Sweet Revenge (1973), containing such fan favorites as "Dear Abby", "Grandpa Was a Carpenter", and "Christmas in Prison", and Common Sense (1975), with "Come Back to Us Barbara Lewis Hare Krishna Beauregard". The latter album was Prine's first to chart on the U.S. Top 100 by Billboard and reflected his growing commercial success. It was produced by Steve Cropper. Bruised Orange from 1978 is a Steve Goodman–produced album that gave listeners songs such as "That's The Way That The World Goes 'Round", "Sabu Visits the Twin Cities Alone", "Fish and Whistle", and the title track.

In 1974, singer David Allan Coe achieved considerable success on the country charts with "You Never Even Called Me by My Name", co-written by Prine and Goodman. The song good-naturedly spoofs stereotypical country music lyrics to create what it self-describes as "the perfect country and western song". Prine refused to take a songwriter's credit (stating he was too drunk when the song was written to remember what he had contributed) and Goodman received sole credit. Goodman bought Prine a jukebox as a gift from his publishing royalties.

In 1975, Prine toured the U.S. and Canada with a full band featuring guitarist Arlen Roth.

The 1979 album Pink Cadillac features two songs produced by Sun Records founder Sam Phillips, who by this time rarely did any studio work. The song "Saigon" is about a Vietnam veteran traumatized by the war ("The static in my attic's gettin' ready to blow"). During the recording, one of the guitar amplifiers blew up (which is evident on the album). The other song Phillips produced is "How Lucky", about Prine's hometown.

In 1981, rejecting the established model of the recording industry, which Prine felt exploited singers and songwriters, he co-founded the independent record label Oh Boy Records in Nashville, Tennessee. His fans, supporting the project, sent him enough money to cover the costs, in advance, of his next album. Prine continued writing and recording albums throughout the 1980s. His songs continued to be covered by other artists; the country supergroup The Highwaymen recorded "The 20th Century Is Almost Over", which had been written by Prine and Goodman. Steve Goodman died of leukemia in 1984 and Prine contributed four tracks to A Tribute to Steve Goodman, including a cover version of Goodman's "My Old Man".

In 1991, Prine released the Grammy Award-winning The Missing Years, his first collaboration with producer and Heartbreakers bassist Howie Epstein. The title song records Prine's humorous take on what Jesus did in the unrecorded years between his childhood and ministry. In 1995, Lost Dogs and Mixed Blessings was released, another collaboration with Epstein. On this album is the long track "Lake Marie", a partly spoken word song interweaving tales over decades centered on themes of "goodbye". Bob Dylan later cited it as perhaps his favorite Prine song. Prine followed it up in 1999 with In Spite of Ourselves, which was unusual for him in that it contained only one original song (the title track); the rest were covers of classic country songs. All of the tracks are duets with well-known female country vocalists, including Lucinda Williams, Emmylou Harris, Patty Loveless, Dolores Keane, Trisha Yearwood, and Iris DeMent.

In 2001, Prine appeared in a supporting role in the Billy Bob Thornton movie Daddy & Them. "In Spite of Ourselves" is played during the end credits.

Prine recorded a version of Stephen Foster's "My Old Kentucky Home" in 2004 for the compilation album Beautiful Dreamer, which won the Grammy for Best Traditional Folk Album in 2004.

In 2005, Prine released his first all-new offering since Lost Dogs and Mixed Blessings, the album Fair & Square, which tended toward a more laid-back, acoustic approach. The album contains songs such as "Safety Joe", about a man who has never taken any risks in his life, and also "Some Humans Ain't Human", Prine's protest piece on the album, which talks about the ugly side of human nature and includes a quick shot at President George W. Bush. Fair & Square won the 2005 Grammy Award for Best Contemporary Folk Album. The album contains original songs plus two covers: A.P. Carter's "Bear Creek Blues" and Blaze Foley's "Clay Pigeons".

On June 22, 2010, Oh Boy Records released a tribute album titled Broken Hearts & Dirty Windows: Songs of John Prine. The album features members of the modern folk revival including My Morning Jacket, The Avett Brothers, Conor Oberst and the Mystic Valley Band, Old Crow Medicine Show, Lambchop, Josh Ritter, Drive-By Truckers, Nickel Creek's Sara Watkins, Deer Tick featuring Liz Isenberg, Justin Townes Earle, Those Darlins, and Bon Iver's Justin Vernon.

In 2016, Prine was named winner of the PEN/Song Lyrics Award, given to two songwriters every other year by the PEN New England chapter. The 2016 award was shared with Tom Waits and his songwriting collaborator wife Kathleen Brennan. Judges for the award included Peter Wolf, Rosanne Cash, Paul Simon, Elvis Costello, and Bono, as well as literary judges Salman Rushdie, Natasha Tretheway, and Paul Muldoon. In 2016, Prine released For Better, or Worse, a follow-up to In Spite of Ourselves from 1999. The album features country music covers spotlighting some of the most prominent female voices in the genre, including; Alison Krauss, Kacey Musgraves, and Lee Ann Womack, as well as Iris DeMent, the only guest artist to appear on both compilation albums.

On March 15, 2017, the American Currents exhibit opened at the Country Music Hall of Fame. The exhibit featured a pair of cowboy boots and jacket that Prine often wore on stage, his personal guitar, and the original handwritten lyric to his hit, "Angel From Montgomery". The American Currents Class of 2016 showcased artists who made a significant impact on country music in 2016, including, Prine. Prine won his second Artist of the Year award at the 2017 Americana Music Honors & Awards after previously winning in 2005.

On February 8, 2018, Prine announced his first new album of original material in 13 years, titled The Tree of Forgiveness, would be released on April 13. Produced by Dave Cobb, the album was released on Prine's own Oh Boy Records and features guest artists Jason Isbell, Amanda Shires, Dan Auerbach, and Brandi Carlile. Alongside the announcement, Prine released the track "Summer's End". The album became Prine's highest-charting album on the Billboard 200.

In 2019, he recorded several tracks including "Please Let Me Go 'Round Again"—a song which warmly confronts the end of life—with longtime friend and compatriot Swamp Dogg in his final recording session.

The last song Prine recorded before he died was "I Remember Everything", released on June 12, 2020, alongside a music video. It was released following the two-hour special tribute show, A Tribute Celebrating John Prine aired on June 11, 2020, which featured Sturgill Simpson, Vince Gill, Jason Isbell, Kacey Musgraves, Bonnie Raitt, Rita Wilson, Eric Church, Brandi Carlile and many other country artists and friends. On the first night of the 2020 Democratic National Convention, Prine singing "I Remember Everything" was the soundtrack to the COVID-19 memorial video.

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