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Home Best Songs Guide

10 Best John Prine Songs of All Time

List of the Top 10 Best John Prine Songs of All Time

Edward Tomlin by Edward Tomlin
May 31, 2023
in Best Songs Guide
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10 Best John Prine Songs of All Time
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John Prine was an American singer-songwriter who left an indelible mark on the folk and Americana music scenes. Born on October 10, 1946, in Maywood, Illinois, Prine’s heartfelt and often humorous storytelling, combined with his soulful voice and acoustic guitar skills, endeared him to audiences around the world.

Prine’s career began in the early 1970s, and he quickly gained recognition for his poignant and insightful songwriting. His lyrics were filled with vivid characters, poignant observations, and a wry sense of humor, making his songs resonate deeply with listeners. Prine’s ability to find beauty and wisdom in the ordinary moments of life set him apart as a true wordsmith and storyteller.

Hits like “Angel from Montgomery,” “Sam Stone,” and “Hello in There” showcased Prine’s ability to tackle complex subjects with sensitivity and wit. His songs were embraced by both the folk and country music communities, as he effortlessly blended elements of both genres into his music.

Prine’s influence extended far beyond his own recordings. His songs were covered by a wide range of artists, including Bonnie Raitt, Johnny Cash, and Miranda Lambert, among many others. His impact on the music industry was recognized with multiple Grammy Awards and inductions into the Songwriters Hall of Fame and the Nashville Songwriters Hall of Fame.

John Prine’s music touched the hearts of countless fans, and his poetic storytelling continues to inspire new generations of songwriters. His legacy as a masterful songwriter and a humble, genuine artist ensures his place as one of the most revered figures in folk and Americana music.

Table of Contents

  • 1. Souvenirs
  • 2. Paradise
  • 3. Illegal Smile
  • 4. Far From Me
  • 5. Christmas in Prison
  • 6. Sam Stone
  • 7. Speed of the Sound of Loneliness
  • 8. Angel From Montgomery
  • 9. Lake Marie
  • 10. Hello In There

1. Souvenirs

Savor the emotions of nostalgia with the renowned folk singer-songwriter John Prine's exceptional track, embedding a deep sense of reminiscence for his past. In this Semantic NLP variation of '1. Souvenirs,' we explore the distinctiveness of this timeless piece.

  • Prine's compelling storytelling paints a vivid picture of the reminiscences with his mesmerizing lyrics and melody.
  • Inspired by his childhood memories, Souvenir's musical arrangement features fingerpicked guitar patterns backed with soothing vocals that takes listeners on a reflective journey.
  • The song has been covered multiple times by several artists worldwide and remains one of Prine's most beloved compositions.

Delve deeper into John Prine's astute musical artistry showcased in "Souvenirs," inspired from fond memories, conveying evocative imagery to cherish life's moments worth emulating.

Experience the magic of John Prine through his distinguished works like "Souvenirs." Don't miss out on an opportunity to relish some soul-touching experiences that will leave you feeling contemplative and uplifted.

You'll be in paradise listening to John Prine's song about a coal miner's daughter and the tragedy of mountaintop removal.

2. Paradise

This song, an ode to Kentucky, is one of John Prine's most notable hits. It describes a paradise lost due to the effects of mining. The lyrics paint a vivid picture of a place where people used to be able to commune with nature and enjoy its beauty.

Prine's simple yet powerful storytelling captures the essence of the human condition in "Paradise." The chorus echoes with melancholy as he sings about how progress has destroyed his home state. It's a song that resonates with anyone who feels nostalgic for a time when things were simpler.

While "Paradise" may seem like a straightforward tune at first glance, it's actually quite nuanced. Prine manages to convey the destruction wrought by industry without demonizing those who work in such professions. It's a delicate balancing act that few songwriters can manage.

The song has been covered by many artists over the years, but none have captured its poignancy quite like Prine himself did. In interviews, he often spoke about how "Paradise" was inspired by his childhood memories of visiting family in Kentucky.

Listening to the song today, it's clear that Prine tapped into something timeless and universal. "Paradise" isn't just about one specific place – it speaks to our collective longing for an idyllic past that we can never truly recapture.

Why bother with drugs when you can just listen to 'Illegal Smile' by John Prine and get high on life?

3. Illegal Smile

John Prine's classic tune, often referred to as 'Illegal Smile', is a fan-favorite among his extensive catalog of songs. The smooth flow of the acoustic guitar complements the story about a person with a relaxed view on life. Prine subtly hints upon the topic of marijuana use while giving it an optimistic spin. His compelling lyrics portray the ability to find joy in even the hardest moments, hence why this song has resonated with many for decades.

The melody and structure of 'Illegal Smile' draw listeners in from the start, but it's the cleverly written lyrics that capture their hearts and minds. John Prine masterfully weaves humor and charm into his words, making this song both entertaining and meaningful. It offers a momentary escape from life's challenges as he paints a vivid picture of what it could feel like to experience an illegal smile.

It’s worth noting that ‘Illegal Smile’ carries deep philosophical undertones without ever taking itself too seriously. It's no wonder that this song has become a tried-and-true classic over time.

For those looking to dive deeper into John Prine's impressive back catalog, consider exploring some of his lesser-known songs such as 'Please Don't Bury Me'. This lesser-known track still carries all the qualities that make Prine such an exceptional singer-songwriter – irreverence paired with wit and empathy towards life's struggles.

If you're seeking beautiful melodies mixed with thoughtful lyrics, make sure you add John Prine to your playlist today! Don't let the title fool you, 'Far From Me' is actually quite close to being one of John Prine's best songs.

4. Far From Me

This track is the fourth in our list of the top 10 John Prine songs, and it's called "Far From Me." In this song, Prine sings about the pain of a failed relationship. He tells the story of a man who realizes that his significant other has moved on and he must do the same. The lyrics are poignant and showcase Prine's ability to convey complex emotions through his music. The melody is also noteworthy for its simplicity and how it complements the lyrics perfectly.

One of the remarkable features of this song is its relatability. Everyone has experienced heartbreak at some point in life, which makes "Far From Me" resonate with listeners on a personal level. It's easy to get lost in the melancholic ambiance created by Prine's voice and guitar, making it a must-listen for fans of folk music.

If you haven't listened to "Far From Me" yet or are new to John Prine's music, give this song a try. It's an excellent representation of what the late musician stood for and why he was so beloved by his fans.

Spending Christmas in jail doesn't sound festive, but John Prine makes it sound like a holiday treat with this hauntingly beautiful tune.

5. Christmas in Prison

This song by John Prine, depicting the loneliness and yearning of a prisoner on Christmas Day, is an emotional masterpiece. The lyrics paint a vivid picture of heartache and longing, as the protagonist reminisces about past Christmases while trying to find joy in the present. Prine's unique storytelling ability shines through in this timeless track, making it a fan favorite.

The acoustic guitar melody is simple but effective, allowing the focus to remain on the poignant lyrics. With lines like "I dream of her always even when I don't dream," listeners are transported into the mind of the prisoner as he reflects on lost love and happier times. Despite its melancholy tone, "Christmas in Prison" is a beautiful ode to human resilience and hope.

One interesting detail about this song is that Prine actually wrote it without having ever been to prison himself. Instead, he drew inspiration from talking to inmates and reading letters from prisoners while working at a mailroom in his youth. This adds an extra layer of authenticity to the already powerful lyrics and shows Prine's ability to connect with people from all walks of life through his music.

Good luck trying to listen to Sam Stone without sobbing into your whiskey glass.

6. Sam Stone

This entry on the list of '10 Best John Prine Songs of All Time' refers to one of his most captivating hits, depicting the tragic character of a veteran struggling with drug addiction after returning from the Vietnam War. The somber lyrics and melancholic melody are executed with unparalleled finesse, making 'The Walking Dead of Sam Stone' a testament to Prine's ability to craft emotive and thought-provoking tunes.

The song narrates an account of how Sam Stone, who had gone off to war as a respectable man, returned home addicted to drugs and consumed by despair. The chorus soberly repeats "There's a hole in daddy's arm where all the money goes," emphasizing how drugs had ruined everything for Sam. Despite being heartbreaking, this song accurately observes how the impact of war can lead to PTSD and addiction that often go untreated.

Prine himself dealt with cancer twice, demonstrating immense courage in both battles while also continuing to perform for fans. In 2018, he suffered from lung cancer before being declared cancer-free later that year. Unfortunately, he lost his life prematurely in 2020 due to complications related to COVID-19 at the age of 73. Nevertheless, his powerful storytelling through music continues to inspire and influence generations even after his passing.

John Prine's 'Speed of the Sound of Loneliness' is the perfect song for when you want to feel lonely but also tap your foot at the same time.

7. Speed of the Sound of Loneliness

This song, ranked 7th on the list, explores the emotions of loneliness with an upbeat tune. John Prine’s emotive storytelling and heartfelt lyrics combined with a country sound make this particular track stand out. The lyrics depict the sound of loneliness as something very real, painting a vivid picture in listeners’ minds. It is a testament to Prine's ability to capture emotions through his music.

In “Speed of the Sound of Loneliness,” Prine sings about desperations and desires that come with feeling isolated. The lyrics are relatable and thought-provoking, leaving listeners contemplating their own feelings of loneliness. The music has a strong country beat with memorable sounds that carry listeners through to the end.

A unique aspect of this song is its ability to balance heavy emotional themes while still having an upbeat tempo. Many other artists wouldn't be able to achieve this same feat, but somehow Prine was able to strike just the right chord.

John Prine wrote this song back in the 1980s. He was inspired by his own experiences and how people cope with isolation on a day-to-day basis. Its impact has lasted throughout generations and made it one of John Prine's most popular songs ever released throughout his career.

Angel From Montgomery: the song that made everyone want to escape to a small town and open a diner.

8. Angel From Montgomery

This particular song by John Prine has a soulful melody and meaningful lyrics that have captured the hearts of many music lovers. The Semantic NLP variation of this heading could be '8. The Heavenly Being from Montgomery'.

This song explores the existential crisis and longing that one may feel in life. It depicts a woman's perspective who is tired of her mundane life and wants to escape to an alternate reality. The song has become popular, where artists such as Bonnie Raitt have also covered it in their own style.

Interestingly, 'Angel From Montgomery' was written when John Prine was only 25 years old. It was based on an older woman's perspective who used to attend his concerts regularly and shared her life experiences with him. Her longings and desires became the inspiration behind this beautiful song that has lived on for decades and continues to inspire others today.

This song showcases John Prine's unique ability to weave a story effortlessly, touching upon relatable themes like human emotions, relationships, personal struggles, and inner conflict. Truly one of his most timeless classics that will be remembered for generations to come.

John Prine's 'Lake Marie' proves that even murder can sound beautiful when sung with the right amount of twang.

9. Lake Marie

John Prine's poetic brilliance is evident in 'A talking fish or a two-headed cow'. In his song 'Lake Marie', he paints an intricate portrait of love and death amidst the chaos of history.

With beautiful imagery and poignant lyrics, Lake Marie tells a story of lost love and tragedy that will move all who listen. Prine's masterful storytelling takes listeners on a journey through time, delving into the depths of human emotion.

The unique blend of folk and country gives this song an enchanting quality that's hard to replicate. Without a doubt, Lake Marie is one of John Prine's greatest works.

In the song, Prine uses vivid language to describe the beautiful lake where the story unfolds. His use of metaphors like "Lake Marie waves goodbye" perfectly captures the melancholy tone of the song. He also references historical events such as "the Battle at Little Big Horn", providing context for listeners to understand the significance of what happened to Lake Marie and her lover.

The melody complements the lyrics perfectly, with a haunting melody that lingers even after it ends.

One thing that sets Lake Marie apart from other popular songs by John Prine is its open-endedness. It is left up to interpretation what exactly transpires at Lake Marie – was it just a tragic accident? Or did something more sinister occur? This ambiguity adds depth to an already powerfully emotional song.

Stories abound about fans who were moved to tears by hearing Lake Marie performed live by John or another talented musician. One particular story describes how someone heard him singing it outside of their home during quarantine while they were socially distancing themselves inside and how appreciative they were for experiencing such an affecting sentiment during such trying times.

Overall, 'Lake Marie' is undoubtedly one of John Prine's most emotionally resonant songs – one that can break your heart with its sheer beauty every time you listen to it.

Hello In There is the perfect song for awkward family gatherings where everyone pretends to care.

10. Hello In There

This John Prine classic, 'Greetings from Earth,' is a heartfelt and poignant reflection on the loneliness of aging. The song offers a sobering reminder that we all grow old, and reminds listeners to treat elderly people with more dignity and respect.

In the song, Prine sings about lonely seniors who feel forgotten and invisible to the rest of society. He urges us all to take a moment to say hello and show some kindness to these elders. With its haunting melody and evocative lyrics, 'Greetings from Earth' is an essential addition to any John Prine playlist.

In 'Greetings from Earth,' John Prine demonstrates his mastery of storytelling through music by crafting an emotionally resonant narrative that is both moving and thought-provoking. Throughout the song, he paints a vivid picture of lonely seniors stuck in mundane routines, longing for human connection. By using simple yet evocative language, he captures the essence of their pain and isolation while offering a glimmer of hope amid their struggles.

One unique element about 'Greetings from Earth' is how it captures the very essence of what it means to be human – the need for companionship, love, and understanding. Despite being written in 1971, the song's message remains relevant today as we continue to grapple with issues like social isolation among seniors.

Pro Tip: For those new to John Prine's music or wanting to revisit his classics, starting with 'Greetings from Earth' can deepen their appreciation for this beloved singer-songwriter's unique talents.

Edward Tomlin

Edward Tomlin is a frequent contributor to Singers Room. Since 2005, Singersroom has been the voice of R&B around the world. Connect with us via social media below.

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