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15 Best John Prine Songs of All Time (Greatest Hits)

June 30, 2023
john prine songs

You’re in luck because today we’re going to take a deep dive into the 15 best John Prine songs of all time.

Prine was a prolific songwriter who left his mark on the music industry with his unique blend of country, folk, and Americana.

His music was characterized by his witty and insightful lyrics, his warm and gravelly voice, and his ability to tell stories that resonated with audiences.

From his early days as a mailman in Chicago to his later years as a revered musician, John Prine’s songwriting was always honest, heartfelt, and authentic.

His songs tackled a range of topics, from love and loss to politics and social issues.

Whether you’re a die-hard fan or just discovering Prine’s music for the first time, this list of his 15 best songs is sure to inspire and delight.

So sit back, relax, and get ready to discover some of the greatest hits of one of America’s most beloved songwriters.

1. “You Never Even Called Me By My Name”

“You Never Even Called Me By My Name”, but don’t worry, it’s still one of the best John Prine songs ever.

Released in 1975, this song is a classic example of Prine’s witty and humorous songwriting. It tells the story of a man who’s been through heartbreak and disappointment but still manages to find humor in his situation.

The song’s chorus is especially memorable, as it references David Allan Coe’s famous song “You Never Even Called Me By My Name”, and adds a humorous twist.

Prine’s unique ability to combine humor and heartbreak is what makes this song so special, and why it remains popular among his fans today.

2. “Illegal Smile”

Get ready to grin when you hear the playful lyrics of “Illegal Smile”.

This song is one of John Prine’s most popular and beloved tunes, and it’s easy to see why.

The lighthearted melody is matched perfectly with the tongue-in-cheek lyrics, which tell the story of someone who finds joy in getting high despite the risks.

Despite the subject matter, the song never feels preachy or judgmental.

Instead, it’s a celebration of life’s small pleasures and an ode to those who choose to live life on their own terms.

It’s no wonder why “Illegal Smile” has become a fan favorite and a staple of John Prine’s live shows.

3. “Mental Cruelty”

The haunting melody and raw lyrics of “Mental Cruelty” transport you to a place of emotional turmoil, capturing the pain and heartbreak of a toxic relationship.

John Prine’s ability to convey complex emotions through simple language is on full display in this song, as he sings about the mental cruelty inflicted by a lover who takes pleasure in causing pain.

The sparse instrumentation, with only a guitar and a harmonica, adds to the rawness of the song and allows the lyrics to take center stage.

“Mental Cruelty” is a testament to Prine’s songwriting prowess and his ability to capture the human experience in all its complexity.

4. “Angel From Montgomery”

Listening to “Angel From Montgomery” transports you to a place of longing and introspection, as Prine’s lyrics and soulful vocals capture the yearning for something more in life.

The song tells the story of a woman trapped in a mundane and unfulfilling life, dreaming of a way out.

The song has been covered by countless artists, including Bonnie Raitt, who made it a hit in her own right.

It has become a timeless classic and one of Prine’s most beloved works.

5. “Everything Is Cool”

When you hear “Everything Is Cool”, Prine’s clever wordplay and upbeat melody will have you tapping your feet and singing along.

This song, off his 1991 album The Missing Years, showcases Prine’s ability to weave together humor and heartbreak.

The lyrics tell the story of a man who has lost everything in a flood but remains optimistic and content with his situation.

The chorus, “Everything’s cool”, everything’s okay,’ is sung with such conviction that it’s hard not to believe it yourself.

The instrumentation, with its driving rhythm and catchy guitar riffs, perfectly complements the song’s message of resilience in the face of adversity.

“Everything Is Cool” is just one example of why John Prine is considered one of the greatest songwriters of all time.

6. “In Spite of Ourselves”

Now, let’s talk about one of John Prine’s most beloved songs, “In Spite of Ourselves”.

This tune was released in 1999 and features Prine singing alongside country singer Iris DeMent.

It’s a playful and humorous duet about a couple who love each other deeply, even though they both have their quirks and flaws.

The song is a fan favorite, and it’s easy to see why.

The lyrics are witty and relatable, and the melody is catchy and fun.

It’s the kind of tune that will have you tapping your foot and singing along in no time.

So, if you’re looking for a feel-good song that will put a smile on your face, give “In Spite of Ourselves” a listen.

7. “Some Humans Ain’t Human”

You’ll be struck by the biting honesty and social commentary in “Some Humans Ain’t Human”, as Prine cleverly exposes the hypocrisy and corruption in modern society.

With a catchy melody and clever lyrics, the song comments on the greed and selfishness that exist in the world today.

Prine’s insightful lyrics highlight the importance of treating others with respect and kindness and the consequences of failing to do so.

The song’s message is relevant and thought-provoking, and it’s no wonder that it has become one of Prine’s most popular and enduring tracks.

“Some Humans Ain’t Human” is a powerful reminder of the need to strive for a more just and compassionate world.

8. “Sam Stone”

Listen to how “Sam Stone” a haunting story of addiction and war is beautifully captured in Prine’s soulful vocals and poignant lyrics.

The song tells the story of a veteran who returns home from the Vietnam War with a drug addiction that ultimately leads to his demise.

Prine’s lyrics paint a vivid picture of the struggles and pain that “Sam Stone” goes through, and the emotive delivery of his vocals brings the character to life.

The song is a powerful commentary on the impact of war on individuals and the toll it takes on their mental health.

It’s no wonder that “Sam Stone” is considered one of the best John Prine songs of all time, as it showcases his ability to craft a compelling narrative with heart-wrenching lyrics and soulful musicality.

9. “Lake Marie”

Now that we’ve explored the heartbreaking tale of “Sam Stone”, let’s shift our focus to a song that takes a slightly different approach.

“Lake Marie” is a track that showcases John Prine’s storytelling abilities in a unique way.

This song intertwines two narratives: one about a couple’s relationship and the other about a group of Native Americans and their history.

The way Prine weaves these two tales together is impressive, and it’s hard not to be drawn in by the vivid imagery and emotional depth of the lyrics.

“Lake Marie” is a standout track not just because of its intricate storytelling, but also because of its catchy melody and upbeat tempo.

It’s a song that showcases Prine’s ability to explore complex themes with a light touch, making it a standout track in his already impressive catalog of songs.

10. “Summer’s End”

When you hear the melancholic melody of “Summer’s End”, you can’t help but feel a sense of nostalgia for the fleeting moments of warm weather and the bittersweet memories that come with it.

As one of John Prine’s most beloved songs, “Summer’s End” captures the essence of the changing seasons and the passage of time.

With its haunting lyrics and simple yet powerful instrumentation, the song speaks to the universal experience of saying goodbye to those we love and the inevitable passage of time.

Prine’s ability to convey complex emotions in his music is unparalleled, and “Summer’s End” is a testament to his skill as a songwriter.

Whether you’re reflecting on your own memories of summers past or simply appreciating the beauty of Prine’s music, “Summer’s End” is a song that will resonate with you long after the final notes have faded away.

11. “Paradise”

If you’re feeling a bit down and in need of a pick-me-up, take a moment to escape to the idyllic world of “Paradise” with John Prine’s soothing voice and calming lyrics.

This classic song, released in 1971, tells the story of a small town in Kentucky that has been destroyed by strip mining.

Prine’s vivid descriptions of the town’s once-beautiful landscape and the effects of the mining on the people who lived there are both heartbreaking and powerful.

The simple melody and gentle guitar strumming add to the song’s peaceful and reflective tone.

“Paradise” is not only a beautiful tribute to a lost way of life but also a poignant reminder of the importance of protecting our natural resources.

It remains one of John Prine’s most beloved and enduring songs and a testament to his talent as a songwriter who could capture the essence of a place and a people with just a few well-chosen words.

12. “That’s the Way the World Goes Round”

You’ll find yourself tapping your foot and nodding your head along to the catchy beat of “That’s the Way the World Goes Round”, a fun and upbeat song that captures the unpredictable nature of life.

With its playful lyrics and upbeat melody, it’s no wonder that this song has become a fan favorite.

John Prine’s unique blend of humor and insight make this song a standout track in his catalog.

From the clever wordplay to the catchy chorus, “That’s the Way the World Goes Round” is a song that you’ll find yourself humming long after the music has stopped.

13. “Souvenirs”

Now that you’ve enjoyed the upbeat tempo of “That’s the Way the World Goes Round”, let’s slow things down and dive into the sentimental tune “Souvenirs”.

This ballad takes you on a journey through the memories of a past relationship.

Prine’s tender voice and poetic lyrics paint a vivid picture of the bittersweet nostalgia that comes with reminiscing on old keepsakes.

The guitar strums and piano notes blend seamlessly, creating a gentle melody that perfectly complements the wistful lyrics.

It’s no wonder why “Souvenirs” is considered one of the best John Prine songs of all time.

It showcases his ability to capture the complexities of human emotions and relationships in a way that resonates with listeners long after the song ends.

14. “Six O’Clock News”

As you listen to the melancholic melody of “Six O’Clock News”, you can’t help but feel the weight of the world on your shoulders, as Prine’s vivid storytelling transports you to the scene of a tragic event.

In this song, Prine sings about a young soldier who gets killed in Vietnam, and how the news of his death is delivered to his family.

The lyrics are poignant and powerful, capturing the pain and heartbreak of war.

Prine’s voice is gentle and emotive, adding to the sadness of the song.

“Six O’Clock News” is a masterpiece of storytelling and one of Prine’s most haunting and memorable songs.

15. “Grandpa Was a Carpenter”

When you hear “Grandpa Was a Carpenter”, you’ll feel the warmth of Prine’s storytelling.

He sings about his grandfather’s life as a hardworking carpenter.

The song is a tribute to the simple life and hard work that his grandfather lived.

It showcases Prine’s ability to tell a story through song.

The lyrics are full of vivid imagery, and the melody is simple and catchy.

It’s a classic John Prine song that will make you smile and appreciate the simple things in life.

It’s a testament to Prine’s talent as a songwriter that he can take a simple topic like his grandfather’s life and turn it into a timeless classic that people still enjoy today.

Best John Prine Songs of All Time – Final Thoughts


You’ve just discovered the 15 best John Prine songs of all time.

Each one of these songs carries with it a memorable tune, powerful lyrics, and a unique story.

You can’t help but get lost in the magic of each song as you listen to Prine’s soulful voice.

Whether you’re a fan of country, folk, or rock, John Prine’s music transcends genres and speaks to the human experience.

From the fun and upbeat “That’s the Way the World Goes Round” to the emotional and heart-wrenching “Angel From Montgomery”, Prine’s songs have a way of touching your heart and soul.

So, sit back, relax, and let the music of John Prine take you on a journey.

You won’t regret it.

With his passing in 2020, these songs are a great way to celebrate his legacy and the impact he had on the music world.

So, turn up the volume and enjoy the 15 best John Prine songs of all time.

You may also like: Best Country Songs of All Time

Will Fenton

Will, the founder of MIDDER, is a multifaceted individual with a deep passion for music and personal finance. As a self-proclaimed music and personal finance geek, he has a keen eye for futuristic technologies, especially those that empower creators and the public.

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