John Prine Best Songs
On The Acoustic

Here on this John Prine best songs page you'll find a collection of John Prine covers as I play them on the acoustic as well as full lesson tutorials available for purchase if required. The demos and chord sheets are free and in downloadable .pdf format. Help yourself to any useful resources on this page.

You'll notice I'm using John Prine album covers as images to indicate which album the song can be found.

Angel From Montgomery is featured on his 1971 self-titled debut, John Prine’s and is a cornerstone of folk and Americana. Though never a hit single for Prine himself, the song achieved legendary status through its profound storytelling and numerous cover versions.

The lyrics center on Bonnie, a woman yearning for escape from a stagnant, unfulfilling life. Through her eyes, Prine explores universal themes of longing, regret, and the search for meaning. Despite the lack of an official music video, the song's emotional depth and poignant melody have made it an enduring classic. It remains one of Prine’s most cherished works, celebrated for its ability to capture the quiet desperation of the human spirit.

Crazy As A Loon was co-written by Prine and his guitar player Pay McLaughlin. The song can be found on his 2005 "Fair & Square" album.

At the 48th Annual Grammy Awards this album won a Grammy for the Best Contemporary  Folk Album.

Crazy Bone is a lighthearted yet thoughtful song from John Prine’s final studio album, The Tree of Forgiveness, released in 2018. Written by Prine along with longtime collaborator Pat McLaughlin, the song reflects Prine’s gift for blending humor, wisdom, and everyday observations into memorable storytelling.

Beneath its playful title and catchy melody lies a message about maintaining perspective and finding joy amid life’s uncertainties. The recording features Prine’s relaxed vocal style and the warm, roots-oriented sound that characterized his later work.

Although not released as a major single, Crazy Bone became a favorite among fans for its uplifting spirit and reminder that laughter and resilience can help carry us through even the most challenging times.

Fish & Whistle is about a tragic event that happened when John was an alter boy and one morning on the way to church, discovered that a local boy got hit from behind by a train while walking on the train tracks.

This song hails from the album Bruised Orange from 1978.

Glory Of True Love John co-wrote with Roger Cook and it is from his Fair And Square album from 2005.

To my knowledge this song was never released as a single. Actually, John Prine only ever released around 6 single throughout his entire musical career.

Hello In There is a track from John's 1971 debut album entitled John Prine.

The song was never released as a single but is a well known tune from the John Prine collection of great story type songs.

I Remember Everything was one of John Prine's final recordings before his passing. "I Remember Everything" was released on June 12, 2020, just a few months after his death.

The song serves as a poignant reflection on life and memories, showcasing John Prine's introspective songwriting style. It received critical acclaim and resonated deeply with his fans, serving as a bittersweet farewell from the legendary singer-songwriter.

Illegal Smile hails from John Prine's debut album "John Prine" from 1971. This song isn't about smoking dope. John said he wrote the song about himself smiling at things that many people never smiled at while he was growing up.

But it happened to fit well with the hippie movement who sort of adopted the song and John never bothered to explain the true source of the song. Download the free John Prine Illegal Smile lyrics below.

Iron Ore Betty is a song about a female construction worker who just happened to spend about 90 minutes with someone John Prine knew in the music biz as they stood in a hotel parking lot having a conversation.

I guess she recognized John's friend and needed a work break in a trailer nearby.  

It's A Big Old Goofy World was written because John's mother Verna liked to play crossword puzzles and that was his inspiration for this song from his 1991 album "Missing Years".

The song was never released as a single to my knowledge.

Killing The Blues was written by Roly Salley who happens to be the bass player for Chris Isaak. Several artists have recorded this song including Shooter Jennings, Robert Plant, Billy Ray Cyrus and others.

The song can be found on the 1979 album "Pink Cadillac".

Knocking On Your Screen Door is a track from John's last album that came out in 2018 called "The Tree Of Forgiveness".

This song was never a single release but there was a music video created by David McClister.

Lonesome Friends Of Science appears on John Prine's 2018 album "The Tree Of Forgiveness".

The Lonesome Friends Of Science chords and lyrics are below.

Magnolia Wind was written by Shawn Camp and Guy Clark. In 2011, a tribute album was put together for Guy Clark and John Prine and Emmylou Harris recorded this song as part of that tribute album.

Guy Clarks version of this song can be found in his album of 2002 called "The Dark".

My Darling Hometown hails form John Prine's 2008 album "Fair & Square" and was written by John Prine and Roger Cook. 

The song was never released as a single.

My Old Man was written by fellow guitar player and good friend Steve Goodman, who wrote this song approx 6 months after his father Bud Goodman passed away. He called John Prine from a payphone and played it for him. 

In 1986 a tribute album to Steve Goodman was put together by various artists and John Prine contributed his talent to this album with this song.

Paradise appears on his debut album from 1971. In the song John makes reference that he wants his ashes spread in the Green River in Kentucky where the town of Paradise Ky is located.

When John passed in 2020, half of his ashes were released in the river and the other half buried next to his parents.

John wrote the song for his father and put it on his debut album. Download the Paradise John Prine chords and lyrics sheet below.

Sam Stone appeared on the 1971 debut album by John Prine and addresses the addiction issue that seems to consume many war veterans after returning from a war environment.

This song is mainly addressing heroin addiction. Download the free Sam Stone John Prine lyrics below.

Same Thing Happened To Me is a quirky, blues-inflected track featured on John Prine’s 1991 Grammy-winning album, The Missing Years. Released on September 24, 1991, the song was not a charting single, yet it remains a favorite for its whimsical take on shared human misfortune.

The track showcases Prine’s signature wit, featuring guest backing vocals from Tom Petty and Phil Everly, which added significant star power to the project. The lyrics humorously recount a series of odd, unfortunate events—like a bird defecating on a suit—to illustrate that bad luck is a universal equalizer. Notably, the album marked a major comeback for Prine, proving his sharp songwriting remained intact decades after his debut.

Souvenirs appears on the John Prine album from 2000 of the same name. Apparently the album was originally intended for release to German audiences only.

Download the John Prine Souvenirs chords and lyrics sheet below.

Speed Of The Sound Of Loneliness hails from Joh Prine's album German Afternoons from 1986.

He recorded the song as a duet with Nanci Griffith in 1993 and she released it as a single. 

Summers End is one of the most poignant songs from John Prine’s 2018 album The Tree of Forgiveness. Written solely by Prine, the ballad explores themes of loneliness, addiction, regret, and redemption with remarkable compassion and emotional depth.

Its unforgettable refrain, “Come on home, you don’t have to be alone,” offers a message of hope and unconditional acceptance to those who have lost their way. The song gained additional recognition through its acclaimed music video, which powerfully expanded on its themes and resonated with audiences around the world.

Widely regarded as one of Prine’s finest late-career compositions, Summer’s End showcases the empathy, storytelling, and humanity that made him one of America’s most respected songwriters.

The Oldest Baby In The World can be found on the John Prine live album from 1988 which was taped over a 3 day period the The Coach House in San Juan Capistrano, California.

John co-wrote this song with Donnie Fritts, who played keyboard for Kris Kristofferson for more than 40 years.

Unwed Fathers was co-written by John Prine and Bobby Bradcock in 1984, the day after the Superbowl. John said he had 15 titles written down and read them off. As soon as Bradcock heard the title, lights went off and they got to work.

This song appears on the 1984 album "Aimless Love".

Your Flag Decal Won't Get You Into Heaven Anymore is a satirical anti-war anthem from John Prine’s self-titled debut album, released in October 1971.

Although it never charted and was not released as a single, it became a cult classic and a staple of Prine’s early career. The song was directly inspired by Prine’s time as a mailman, where he grew frustrated delivering Reader’s Digest magazines that included free flag decals during the Vietnam War.

Prine used the song to mock the "silent majority" and superficial displays of patriotism. Interestingly, he retired the song from his live sets for years because he felt the lyrics were too harsh, only bringing it back by popular request during the Iraq War.