10 Best John Prine Songs of All Time

John Prine was an American singer-songwriter who is widely regarded as one of the most important and influential figures in folk and country music. Prine first rose to prominence in the 1970s with his self-titled debut album, which included hits like “Sam Stone,” “Hello in There,” and “Angel from Montgomery.”

Prine’s music is characterized by his poetic lyrics, wry sense of humor, and soulful vocals. His songs often explored themes of love, loss, and the struggles of everyday life, and his ability to convey deep emotion through his music helped to make him one of the most beloved and respected singers of his time.

Despite numerous health challenges in later years, Prine continued to tour and record music up until his death in 2020. He was recognized for his contributions to music with multiple awards and honors, including induction into the Songwriters Hall of Fame and the Grammy Lifetime Achievement Award.

Prine’s influence on the development of folk and country music cannot be overstated. His poetic lyrics and powerful storytelling have inspired countless other musicians, and his music continues to be celebrated and admired by fans around the world. His legacy as a trailblazer and innovator in the world of folk and country music is secure, cementing his place as one of the most important and beloved singers of his generation.

1. Souvenirs

The first track on our list embodies John Prine's ability to craft emotive and reflective lyrics that resonate with listeners long after the song has ended. "1. Souvenirs" takes us on a tender journey through memories of lost love, tied together by Prine's heartfelt vocal performance.

• The song was written in 1972 for his self-titled debut album.
• It features imagery and metaphors that highlight the power of nostalgia, such as "Old worn out pictures that my memory saves".
• "Souvenirs" has been covered by numerous artists throughout the years, including Steve Goodman and Susan Tedeschi.

Away from the spotlight, "Souvenirs" was one of Prine's favorite songs to perform among close friends and family. Its delicacy and depth capture his artistic finesse in exploring universal themes through uniquely personal experiences.

Fun Fact: Despite its critical acclaim, John Prine's debut album only sold around 25,000 copies but went on to become a classic amongst country-folk enthusiasts. (Source: RollingStone)

If John Prine's Paradise existed in real life, it would be a great vacation spot, but unfortunately, we'll have to settle for just listening to the song.

2. Paradise

This John Prine classic, about a coal miner's paradise lost to strip mining, strikes a chord with its universal narrative of how greed and modernity can destroy the serene beauty of nature. Its harmonica-infused melody and soulful lyrics make it a timeless gem.

Prine sings about the loss of natural beauty in his hometown, now replaced by artificial creations. The song conveys a sense of mourning for what once was and a warning for what may yet come if we don't take better care of our planet. It is an ode to the purity and simplicity that we could have retained had we not pursued progress at all costs.

In "Paradise" Prine draws on his personal history as he was born into a family of coal miners from Kentucky. He witnessed firsthand the environmental destruction brought on by the long-term mining industry in his hometown. This song stands as an anthem for those concerned with preserving nature despite societal pressure to develop at any cost.

Illegal Smile may not be the one that got John Prine arrested, but it's definitely the song that'll get stuck in your head.

3. Illegal Smile

One of the most widely appreciated works of John Prine embodies the impossible joy, of an illegal smile. An amazing blend of folksy charm and outlaw wit characterizes this art piece. Through its lyrics, Illegal Smile celebrates a state of happiness derived through illegal means as well as playfully challenges authorities and laws.

Illegal Smile is often associated with marijuana; however, John Prine himself has stated that it is open to interpretation and goes beyond drug references. Additionally, this track was featured in his debut album titled 'John Prine' released in 1971 which propelled him into the world of songwriting and paved his way towards becoming a respected music icon.

Far From Me is like a breakup song on steroids – it's so good, it'll make you want to break up with your current favorite John Prine song.

4. Far From Me

This song, written by John Prine and released in 1980, is a powerful ballad that depicts the emotional turmoil of a past relationship. The lyrics are deeply introspective, capturing the essence of unrequited love and lost opportunities. With its poignant storytelling, "Far From Me" showcases Prine's gift for weaving intricate narratives with simple words and vivid imagery. The mellow guitar accompaniment perfectly complements the subdued mood of the track, adding to its haunting quality. Overall, "Far From Me" is a quintessential John Prine song that embodies his unique blend of honesty and vulnerability.

The song draws on autobiographical experiences from Prine's life, particularly his failed marriage to childhood sweetheart Ann Carole Bowles. The couple met when they were just 14 years old and married in 1966, but their relationship was fraught with difficulties. Prine's burgeoning music career put a strain on their marriage as he spent extended periods touring and recording. Eventually, the couple divorced in 1971, inspiring many of Prine's early songs such as "Paradise" and "Angel From Montgomery". "Far From Me" is another poignant reflection on the demise of their relationship, offering insights into both regret and acceptance.

Interestingly enough, many artists have covered this song over the years including Bonnie Raitt and Justin Vernon (of Bon Iver fame). Its timeless appeal speaks to its universal themes that continue to resonate with audiences today. "Far From Me" remains one of John Prine's most beloved songs – an intimate glimpse into his soulful perspective on love and heartbreak.

Christmas in prison may not be the most festive, but John Prine turns it into a heart-warming tale with his signature wit and charm.

5. Christmas in Prison

This haunting ballad captures the agony of spending the holiday season behind bars. In the song named after a holiday, John Prine narrates a prisoner's experience on Christmas. The lyrics take you down memory lane as they describe past Christmases and what it feels like to spend one in prison. The verses paint vivid pictures of loneliness, regret, longing, and resilience amidst tough times.

Throughout the song, Prine's powerful storytelling is backed by an acoustic guitar that sets a solemn tone for the melancholic story he tells. As described by American Songwriter Magazine, this song "is nothing shy of a masterpiece." It has remained one of Prine's most popular songs since it was first released in 1973.

Notably, "Christmas in Prison" has been covered by numerous celebrated artists such as Emmylou Harris and John Legend who did so with soul and ease. It has also been used on multiple TV shows and films like "The West Wing" and "Prison Break."

The prison-love tale was inspired by a letter that John received from his friend Steve Goodman, who proposed the idea to him while watching some inmates trim trees in Cook County Jail.

Sam Stone may have been a Vietnam vet, but listening to his story will make you feel like you've been through war too.

6. Sam Stone

This song portrays an ex-soldier's addiction and subsequent downfall. It's a part of John Prine's self-titled debut album, which was released in 1971. The lyrics are poignant and heartfelt, as Sam Stone returns home with a drug habit after serving in Vietnam, unable to readjust to his old life. As he sinks further into addiction, his family and friends disown him, and he starts living on the streets. This song reflects the harsh reality of war and how it can break soldiers mentally and physically, leading to long-lasting consequences for them and their families.

"Loneliness doesn't have a sound, but if it did, John Prine would have written a heartbreaking melody for it."

7. Speed of the Sound of Loneliness

This John Prine classic, with its melancholy melody and sharp lyrics, tells a story of loneliness and isolation. The song explores the pain and longing that one feels when they are unable to connect with others, and it does so in a way that is both hauntingly beautiful and deeply emotional.

Prine's lyrics perfectly capture the sense of longing that comes with being alone, as he sings about the "speed of the sound of loneliness," which seems to echo endlessly through the empty spaces around us. Yet despite this sadness, there is also a sense of hopefulness in the song's refrain, which reminds us that even in our darkest moments there is always a chance for redemption.

One unique aspect of this song is its use of metaphor to explore complex emotions. For example, Prine compares the sound of loneliness to the ringing of a telephone, suggesting that it is something that never stops calling out to us no matter how hard we try to ignore it.

Interestingly, Prine himself once said that this song was inspired by an actual phone call he received from a friend who was feeling lonely and desperate. This personal connection adds another layer of emotional depth to an already powerful piece of music.

John Prine's 'Angel From Montgomery' is perfect for when you want to wallow in loneliness but also tap your foot to a kickass beat.

8. Angel From Montgomery

This song, which is also known as "Angel," tells the story of a woman stuck in a loveless marriage dreaming of something more. Prine's authentic and raw lyrics paint a vivid picture of her mundane life and longing for escape. Bonnie Raitt famously covered this song and helped popularize it. In an interview with NPR, Prine revealed that he wrote the song from the perspective of an older woman he had met at a laundromat. It remains one of his most beloved and iconic tracks.

John Prine's 'Lake Marie' is the perfect song to simultaneously make you want to dance and question the meaning of existence.

9. Lake Marie

Described as one of Prine's best pieces, the heart-wrenching tale of 'Loss and tragedy in Lake Marie' is elegantly portrayed through his lyrics. Inspired by a news story, this song intricately intertwines multiple stories into a poetic narrative. The skillful wordplay and attention to detail are complemented by an impeccable acoustic melody that emphasizes its somber undertones. Its instrumental use and efficient storytelling make 'Lake Marie' an excellent depiction of his career-defining songwriting style.

In the verses, Prine paints a vivid picture of the events that took place in Lake Marie, with images of couples, young lovers, police officers, and fishing trips woven together to create an immersive listening experience. The chorus serves as a reminder of those who lost their lives in the tragedy. Though hauntingly melancholic, the song shines through Prine's ability to reflect on both loss and life itself with his lyrical abilities.

This masterpiece earned critical acclaim from artists across the music spectrum and was hailed by critics worldwide for its poetic prowess. It remains a timeless classic and embodies all the qualities that make John Prine one of the most celebrated singer-songwriters ever.

Prine's unique ability to weave humor with solemn themes is widely known; however, it is invaluable how he never loses clarity amidst complexity while being introspective about grief itself. This tribute demonstrates John Prine's exceptional skillset in blending melody with lyrics like no other songwriter ever has or will be able to accomplish in such a unique way.

Listening to 'Hello In There' will make you feel like hugging your loved ones tight, or at least texting them a heart emoji.

10. Hello In There

This song tells the heartbreaking story of elderly people being forgotten by society. John Prine's "Hello In There," a masterpiece of folk music, is known for its evocative imagery and poignant message. The lyrics emphasize how easily we overlook the elderly and ignore their feelings until it's too late.

The acoustic guitar in this piece, accompanied by vocals that are both soothing and reflective, perfectly captures the melancholy tone of the message. The harmonies are delicate and airy, while the lyrics remind us how important it is to keep in touch with our elders.

John Prine's "Hello In There" may be a classic composition, but its appeal never grows stale. It has become one of his most enduring compositions to date because it reminds us that even though our elders may no longer be physically strong, they still have valuable stories to tell.

Once you hear this moving ballad about isolation and loneliness, you'll want to share it with everyone you know. Its message will resonate with anyone who has ever felt alone or neglected. Listen closely to John Prine's "Hello In There" and remember the importance of appreciating those around you before they're gone forever.