10 Best John Prine Songs of All Time

John Prine, a revered American singer-songwriter, left an indelible mark on the folk and country music landscape. Born on October 10, 1946, in Maywood, Illinois, Prine’s career spanned over five decades until his passing in April 2020. Renowned for his poignant and often humorous storytelling, Prine’s songwriting reflected a keen observational prowess and a deep understanding of the human condition.

Prine’s eponymous debut album, released in 1971, featured now-classic songs like “Angel from Montgomery” and “Hello in There.” His ability to craft evocative narratives and deliver them with a raw, emotive voice garnered widespread acclaim. Over the years, Prine’s discography grew to include gems like “Paradise,” “Sam Stone,” and “In Spite of Ourselves.”

Despite facing various health challenges, Prine continued to create music that resonated with audiences. His work earned him numerous accolades, including Grammy Awards and the Grammy Lifetime Achievement Award. Prine’s impact extended beyond his own performances, influencing a diverse array of musicians who admired his authenticity and songwriting craftsmanship.

John Prine’s legacy lives on through his timeless songs, which continue to be celebrated for their wit, wisdom, and emotional resonance, making him a revered figure in the pantheon of American folk and country music.

1. Angel from Montgomery

When discussing the song "Angel from Montgomery" by John Prine, it is important to acknowledge its impact and enduring popularity. Released in 1971, this folk-country ballad has resonated with audiences for decades. The lyrics, which portray the struggles of a woman trapped in a loveless marriage, have struck a chord with listeners and have been covered by countless artists. Prine's heartfelt delivery and poignant storytelling make "Angel from Montgomery" a timeless classic that continues to captivate audiences to this day.

2. Sam Stone

Sam Stone is a haunting song by John Prine that tells the story of a Vietnam War veteran struggling with addiction and the aftermath of war. It showcases Prine's ability to capture the complexities of human emotions and experiences with his heartfelt lyrics and soulful melodies. The song highlights the devastating impact of war on individuals and serves as a powerful reminder of the realities faced by veterans.

Fun fact: John Prine received the Grammy Lifetime Achievement Award in 2020 for his contributions to the music industry.

3. Hello in There

"Hello in There" is one of John Prine's most beloved songs. To fully appreciate its beauty and depth, follow these steps:

1. Listen to the lyrics carefully and absorb the powerful message about empathy and compassion.
2. Pay attention to Prine's heartfelt vocals and the delicate melody that perfectly complements the song's poignant lyrics.
3. Reflect on the universal theme of loneliness and the importance of reaching out to others who may be feeling isolated.

If you enjoy "Hello in There," you may also like other Prine classics such as "Angel from Montgomery" and "Sam Stone." These songs showcase Prine's storytelling abilities and his ability to evoke deep emotions through his music.

4. Illegal Smile

"Illegal Smile" is a timeless John Prine classic that highlights his clever songwriting and wit. Through its catchy melody and witty lyrics, the song delves into the concept of finding joy in life's simple pleasures, even if they may not be entirely legal. With its relatable message and Prine's unique storytelling, "Illegal Smile" continues to be a beloved song among fans. Remember to embrace the little things that bring a smile to your face, even if they may not be conventional, when life gets tough. Let the positivity and happiness around you lift your spirits.

5. Paradise

Paradise by John Prine is a timeless classic that captures the beauty and nostalgia of a bygone era. To fully appreciate this song, follow these steps:

1. Listen to the original recording by John Prine to experience the raw emotion and storytelling.
2. Read the lyrics to fully grasp the poetic genius behind the song.
3. Explore cover versions by other artists, like Johnny Cash, who put their own spin on the song.
4. Research the inspiration behind the song, which was John Prine's childhood memories of the coal-mining town of Paradise, Kentucky.
5. Reflect on the universal themes of longing, loss, and the destruction of nature that Paradise addresses.

Fun Fact: The town of Paradise, Kentucky, was indeed affected by coal mining and eventually bought out by the Tennessee Valley Authority, leading to its demise.

6. That's the Way the World Goes 'Round

"That's the Way the World Goes 'Round" is a timeless John Prine song that captures the ups and downs of life. To fully appreciate this song, follow these steps:

1. Listen to the lyrics carefully to understand the witty observations about life's unpredictability.
2. Pay attention to Prine's unique storytelling style, which adds depth to the song.
3. Appreciate the catchy melody and Prine's distinctive vocal delivery.
4. Consider the universal themes of the song, which resonate with listeners of all ages.
5. Explore the song's impact and how it has influenced other artists in the music industry.

Pro-tip: Reflect on the song's message and use it as a reminder to embrace life's twists and turns with a sense of humor and resilience.

7. Far From Me

"Far From Me" is a heartfelt song by John Prine that showcases his lyrical and storytelling prowess. To fully appreciate this beautiful piece of music, you can:

1. Listen to the original version of the song on John Prine's album "Common Sense."
2. Pay close attention to the vivid lyrics that express the pain and longing of lost love.
3. Take note of the delicate guitar picking and Prine's emotive vocal delivery.
4. Explore cover versions of the song by other artists to appreciate different interpretations.

If you enjoy "Far From Me," you might also appreciate other emotionally charged songs by John Prine, such as "Hello in There" and "Angel from Montgomery."

8. Lake Marie

"Lake Marie" is a standout song by John Prine that showcases his storytelling prowess and unique songwriting style.

1. The song tells a compelling narrative about love, loss, and the passage of time.
2. Prine's lyrics are filled with vivid imagery, painting a picture of the characters and their experiences.
3. The melody and instrumentation perfectly complement the emotional depth of the lyrics.
4. "Lake Marie" has resonated with both fans and critics, earning praise for its storytelling and musical craftsmanship.
5. Prine's heartfelt and authentic performance of the song further enhances its impact.
6. The song's universal themes make it relatable to a wide range of listeners.
7. "Lake Marie" showcases Prine's ability to tackle complex subjects with wit, wisdom, and compassion.
8. The song continues to be a beloved favorite among fans of John Prine's music.

9. In Spite of Ourselves

In Spite of Ourselves is a beloved song by John Prine that showcases his wit and storytelling abilities. Here are some steps to fully appreciate this song:

1. Listen to the original version of In Spite of Ourselves featuring Iris DeMent.
2. Pay attention to the clever and humorous lyrics that tell the story of a flawed but enduring love.
3. Appreciate the chemistry between Prine and DeMent as they playfully sing back and forth.
4. Notice the country-folk sound and simple instrumentation that adds to the charm of the song.
5. Explore other versions and covers of the song by artists like Brandi Carlile and Bonnie Raitt.
6. Sing along to the catchy chorus and memorable lines that are sure to put a smile on your face.
7. Reflect on the universal theme of imperfect love and how it resonates with your own experiences.
8. Share the song with friends and family who appreciate good music and a good laugh.
9. Consider adding In Spite of Ourselves to your playlist of feel-good songs that never fail to brighten your day.

10. Bruised Orange (Chain of Sorrow)

To fully appreciate John Prine's song "Bruised Orange (Chain of Sorrow)," follow these steps:

1. Listen attentively to the lyrics and melody, allowing yourself to connect emotionally with the storytelling.
2. Pay attention to the vivid imagery used throughout the song, such as "a bird with a broken wing" or "a girl with too much makeup."
3. Reflect on the theme of resilience in the face of adversity, as portrayed through the metaphor of a "chain of sorrow."
4. Consider the nuanced commentary on the human condition and the universal experiences of pain and struggle.
5. Appreciate Prine's unique storytelling style, blending elements of folk, country, and Americana.
6. Explore other songs from Prine's discography to gain a deeper understanding of his artistry and songwriting prowess.
7. Share and discuss the song with fellow music enthusiasts to foster a meaningful conversation and exchange of perspectives.
8. Research interviews or articles about John Prine to gain insights into his creative process and inspirations.
9. Continue to listen to "Bruised Orange (Chain of Sorrow)" and discover new layers of meaning with each subsequent listen.
10. Finally, explore other songs from John Prine's extensive catalog to discover more gems that resonate with you.

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.