Top 10 John Prine Albums

John Prine Albums

Photo: Ron Baker (, CC BY 3.0 <>, via Wikimedia Commons

John Prine’s music was like a dog – a faithful companion that followed at your heels for years. It could make you laugh, make you mad, and break your heart when you found out about his death from complications of COVID-19. No wonder that for over 50 years, John Prine’s music touched so many people so deeply.

He wrote a wide variety of songs that crossed genres, but all of his songs had his wonderful poetry and unique look at life. Although he did tackle some usual song topics like love, he approached them in a different way. Not many people wrote about lovers who never met. He also wrote about such things like a strip-mined Kentucky town, an elephant-riding actor, and the loneliness of old people. John Prine put out eighteen studio albums, two compilation albums and five live albums. If anyone tells you that picking just ten favorite John Prine albums is easy, know they are lying.

#10 – In Spite of Ourselves

This 1999 offering is a concept album, of sorts. John Prine his voice changing with age and from a successful battle with throat cancer, does (with the exception of one song) a series of duets with country singers like Iris DeMent, Trisha Yearwood, Emmylou Harris, Patty Loveless and his own wife. This is also a heavily-flavored country album, although some songs like “Not the Jet Set”, “Dear John (I Sent Your Saddle Home)” and “In Spite of Ourselves” seem almost parodies of country songs with lyrics about very unconventional lovers. Unlike other John Prine albums, all of the songs except “In Spite of Ourselves” were written by others.

#9 – German Afternoons

John Prine’s music is usually considered cross-genre or hard to classify, but here he delves into his love of country music. On tracks like “Lulu Walls”, he even goes full-on bluegrass. Even someone who doesn’t like country music can find something to like on this album, which features some lovely fiddle playing by Stuart Duncan. This album has many love songs, which was unusual for a John Prine album up until then. The love songs like “Sailin’ Ariound” are beautifully bittersweet and filled with longing for lost love. The album’s best-known song is “Let’s Talk Dirty in Hawaiian,” for obvious reasons. Although many John Prine fans would have been happy for him to make albums like his first few over and over again, John Prine did not agree. This 1986 album received a Grammy nomination but did not win. John Prine would take a few years break from the studio after making this one.

#8 – Lost Dogs and Mixed Blessings

This 1995 album sounds a lot different from many other John Prine albums since it was produced by Howie Epstein, better known as the bassist for Tom Petty and the Heartbreakers. The result is sort of the love child between the Heartbreakers and John Prine. The production seems overdone at times, but the songs are unique and thought-provoking. One of the highlights is a duet with Marianne Faithful on “This Love is Real.” Another highlight is the indescribable “Lake Marie”, which features lyrics like “The dogs were barking as the cars were parking, The loan sharks were sharking and the narcs were narcing.” Makes you think that E. E. Cummings would have approved. Bob Dylan was, calling this his favorite John Prine song. Although it did well critically and received a Grammy nomination, John Prine and Howie Epstein would part ways after this.

#7 – The Missing Years

John Prine took a break from recording in 1986. He didn’t get back into the studio for years. Although many musicians wanted to produce John Prine’s comeback album, Howie Epstein won. This time, Tom Petty himself guest-stars on one song, “Picture Show.” This sounded more like the folk and country-flavored albums of John Prine’s past, but does have pop and rock touches. Other guest stars include Bonnie Raitt and even Bruce Springsteen on a song co-written with John Mellencamp. Contains some funny songs like “It’s A Big Old Goofy World” and “Daddy’s Little Pumpkin”, but also some touching songs like “All the Best”, which John Prine would later describe on an NPR Tiny Desk concert as the ultimate kiss-off song. This would earn John Prine a Grammy for Best Contemporary Folk Album for 1991.

#6 – Fair and Square

This double album contains fully realized songs of both resigned sadness and touching humor. Although the arrangements are country-flavored, you do not have to be a country music fan to appreciate this. Highlights include “Some Humans Ain’t Human” and “Crazy as a Loon.” In other words, it’s another great John Prine album. Originally released in 2205, it was re-released in 2007 with a few bonus tracks. The bonus tracks were also sold separately in an EP. The album won a Grammy for Best Contemporary Folk Album.

#5 – The Tree of Forgiveness

This was John Prine’s last album and one of his most critically acclaimed. It also was a rarity – a John Prine album that sold well. Although there are several light-hearted songs filled with John Prine’s usual humor such as “When I Get to Heaven”, most of the album is bittersweet since both he and the listener know it’s the last one. “Looks like this old horseshoe’s done run out of luck,” he sings in “Boundless Love.” It’s a powerful image for a powerful album. It was released in 2018. It received a Grammy nomination but did not win.

#4 – Bruised Orange

This was the first album John Prine did for his new label Asylum, the last label he would appear on before starting his own label, Oh Boy. Friend Steve Goodman would produce, provide a little guitar and backing vocals. Jackson Browne also appears on backing vocals. The sound is smooth, catchy and thankfully lacks some of the over-production of some later records. Songs include the funny “Fish and Whistle” and “Aw Heck”; a song co-written with Phil Spector, “If You Don’t Want My Love”; and fan favorite “That’s the Way That the World Goes Round”. Some songs also feature beautiful playing by Jim Rothermel of the penny whistle and recorder, two instruments that just do not appear enough on modern records. The album came out in 1978.

#3 – Sweet Revenge

This is one of those albums that becomes an old, reliable friend over the years. Released in 1973, it still sounds pertinent, sad, funny and piercingly insightful today. It includes songs recorded in Nashville and New York City. Steve Goodman contributed some guitar and backing vocals. John Prine had matured as a songwriter with tunes that stick in your head for years – for the right reasons. Songs on the album include fan favorites “Dear Abby”, “Please Don’t Bury Me”, “Often is a Word I Seldom Use” and “Grandpa Was a Carpenter.” It ends with a curious cover of the Merle Haggard song “Nine Pound Hammer”, showing what John Prine could do with a song that made him happy. Also includes a song with a title you don’t see often enough, “Onomonopeia”, a song about the frustrating side of show business.

#2 – John Prine

John Prine had been performing in Chicago for some time. Movie critic Roger Ebert even wrote about one of his shows in 1970. John Prine made friends with fellow folk-country musician Steve Goodman. Steve Goodman managed to persuade Kris Kristofferson to have John Prine open for him. A record executive from Atlantic Records saw the show, and John Prine was offered a record deal. Although he did not like the cover image or the way he sang or the business side of show business, the resulting album included powerful songs that would be part of John Prine’s live shows for most of the rest of his life. They include “Illegal Smile”, “Sam Stone,” about a drug addicted vet and father, the original version of “Angel of Montgomery”, and “Your Flag Decal Won’t Get You into Heaven Anymore.” Most of the songs on this 1971 album have been covered by other artists.

#1 – John Prine Live

Although this live album from 1988 contains many songs found on other John Prine albums, it contains his stories before the songs. The stories, such as for “Sabu Visits the Twin Cities Alone”, which originally came out on Bruised Orange, really bring out a whole new level of meaning. The funny introduction somehow makes the song even sadder. The live performances are just John Prine and a guitar, which is all that is needed. Although most of the album is taken from performances in 1988, there is “Angel of Montgomery”, recorded at a tribute concert for Steve Goodman in 1985. This is a great introduction to John Prine’s music, or to get someone hooked on John Prine.

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