Skip to Content

John Prine’s Timeless Hits (Exploring His Top Songs)

John Prine, a revered figure in the world of Americana and folk music, left an indelible mark on the music industry with his timeless songs and unparalleled storytelling.

Throughout his illustrious career, he penned songs that resonated deeply with audiences, showcasing his ability to capture life’s nuances with humor, wit, and emotion.

In this article, we will delve into the top songs that define John Prine’s legacy, each offering a unique glimpse into his artistry.

1. “Summer’s End” – A Melancholic Masterpiece

An old picture of John Prine
An old picture of John Prine

Summer’s End,” from his 2018 album ‘The Tree of Forgiveness,’ stands as a quintessential Prine track. This song masterfully combines poignant lyrics with carefully crafted instrumentation, offering a bittersweet reflection on the passing of time and the end of summer.

Prine’s ability to infuse hope into melancholy is on full display, making this song an emotional rollercoaster.

2. “Lake Marie” – A Literary Journey

In “Lake Marie,” featured on the 1995 album ‘Lost Dogs and Mixed Blessings,’ Prine takes listeners on a literary journey. This song weaves a complex narrative of abandoned babies and crumbling marriages.

Its upbeat melody contrasts sharply with the dark subject matter, leaving audiences with thought-provoking questions and showcasing Prine’s storytelling prowess.

3. “Sam Stone” – A Poignant Debut

Prine’s debut album, ‘John Prine’ (1971), introduced “Sam Stone,” a deeply moving song that tackles the challenges faced by a war veteran returning to civilian life, ultimately succumbing to drug addiction.

Prine’s deft storytelling paints vivid pictures, and the song’s themes of time’s passage and the fleeting nature of life remain as relevant today as they were upon its release.

Subscribe to Nash Gab on Facebook!
Subscribe so you don't miss a thing.

4. Witty Commentary: “Some Humans Ain’t Human”

His 2005 album ‘Fair & Square,’ “Some Humans Ain’t Human” showcases Prine’s trademark dry wit and social commentary. In this song, he humorously dissects the unkindness of certain individuals while subtly alluding to the political landscape, including the presidency of George W. Bush and the Iraq War.

5. “In Spite of Ourselves” – A Love Story with a Twist

Debuting on his 1999 album, Prine’s “In Spite of Ourselves” is a delightful duet with Iris DeMent. It celebrates the endurance of love despite the quirks and idiosyncrasies that define human relationships.

Prine’s ability to capture the essence of love’s resilience is showcased alongside DeMent’s vivid portrayal of a seemingly unconventional love story.

6. “Everything Is Cool” – An Original Christmas Song

Found on his 2009 holiday album, ‘A John Prine Christmas,’ “Everything Is Cool” presents a unique take on a Christmas song. This track explores themes of love and new beginnings after the end of a relationship, all within a holiday context.

Prine’s lyrical brilliance shines through, making it a standout addition to his discography.

A recent picture of John Prine
John Prine

7. “Angel From Montgomery” – A Classic

From his 2016 album ‘For Better, or Worse,’ “Mental Cruelty” features a playful collaboration with Kacey Musgraves. The song’s clever back-and-forth banter between the two artists perfectly encapsulates their wit and chemistry, making it a standout in Prine’s repertoire of duets.

9. “Illegal Smile” – The Humor of Everyday Life

The opening track of his debut album, “Illegal Smile,” introduced the world to Prine’s clever humor and penchant for storytelling through song. With lyrics that find humor in life’s challenges, it remains a testament to Prine’s unique perspective on the world.

10. “You Never Even Called Me By My Name” – Country Music Satire

Although not originally recorded by Prine, this song, featured on David Allan Coe’s ‘Once Upon a Rhyme‘ (1975), reflects classic Americana tropes and humor. It humorously satirizes the country music industry, aligning Prine and Coe as country music outlaws

A picture of John Prine with his son.
John Prine with his son
Song TitleAlbumYear Released
Summer’s EndThe Tree of Forgiveness2018
Lake MarieLost Dogs and Mixed Blessings1995
Sam StoneJohn Prine1971
Some Humans Ain’t HumanFair & Square2005
In Spite of OurselvesThe Missing Years1999
Everything Is CoolA John Prine Christmas2009
Angel From MontgomeryJohn Prine1971
Songs with their release dates

From Mailman to Musical Icon: John Prine’s Journey to Fame

On October 10, 1946, John Prine was born in Maywood, Illinois. He grew up listening to a variety of music, including country, folk, and rock and roll. He learned to play guitar at a young age and began writing songs as a teenager.

Prine’s interest in music deepened while he was serving in the US Army in West Germany in the late 1960s. During this time, he was exposed to a variety of European music, and he began to develop his own unique songwriting style.

After returning to the United States, Prine began playing open mic nights and small clubs in the Chicago area. He quickly gained a following for his witty and insightful songs, which often dealt with the everyday struggles and triumphs of ordinary people.

John Prine

In 1971, Prine released his self-titled debut album. The album was a critical and commercial success, and it established Prine as one of the leading voices in the folk music revival of the early 1970s.

Over the next few decades, Prine released a string of critically acclaimed albums, including “Diamonds in the Rough” (1972), “Sweet Revenge” (1973), and “Common Sense” (1975). He also wrote songs that were covered by other artists, such as Bonnie Raitt, Johnny Cash, and the Grateful Dead.

Prine’s music has been praised for its honesty, humor, and compassion. He was a master storyteller, and his songs often painted vivid portraits of the human experience.

Prine’s music continues to resonate with audiences of almost all ages, and he is considered one of the most important songwriters of his generation.

Prine died on April 7, 2020, from complications of COVID-19. He was 73 years old.

John Prine’s Hits

Why Are These Songs Considered John Prine’s Best?

These songs are considered John Prine’s best because they showcase his unique songwriting talent and ability to capture the human experience in a way that is both relatable and thought-provoking. They are also some of his most popular songs and have been covered by many other artists.

What Are Some Of The Themes Explored In These Songs?

The themes explored in these songs include love, loss, war, addiction, redemption, and the passage of time. Prine’s songs often deal with the darker side of life, but they always do so with humor, wit, and compassion.

How Can You Listen to These Songs?

These songs can be found on many streaming platforms, such as Spotify, Apple Music, and YouTube Music. They can also be found in many physical formats, such as CDs and vinyl records.

Who Are Some Other Artists Who Have Covered John Prine’s Songs?

Some of the many artists who have covered John Prine’s songs include Bonnie Raitt, Kacey Musgraves, Willie Nelson, and Alison Krauss.


  • John Prine was a master songwriter who wrote some of the most iconic and enduring songs in American popular music.
  • His songs are both relatable and thought-provoking, and they continue to be enjoyed by generations to come. The 10 songs mentioned in this article are just a small sample of his vast and impressive catalog.
  • Prine’s songs are often about the everyday struggles and triumphs of ordinary people. He has a gift for finding humor and pathos in even the most difficult situations.
  • His songs are also often about the beauty of the natural world and the importance of human connection.
  • Prine’s music is a treasure trove of wisdom and insight into the human experience. His songs are both timeless and timely, and they continue to resonate with audiences of all ages.

Other Articles

Skip to content