Best Waylon Jennings Songs
Entertainment & Playlists

14 Best Waylon Jennings Songs of All Time (Greatest Hits)

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Written By Will Fenton
Entertainment & Playlists

14 Best Waylon Jennings Songs of All Time (Greatest Hits)

Join us on a captivating musical journey as we delve into the incomparable talent of one of country music’s true legends, Waylon Jennings.

With a career spanning several decades, Waylon Jennings left an indelible mark on the genre, forever cementing his status as an icon.

In this article, we pay tribute to the 14 best songs ever crafted by this remarkable artist.

From his rebellious outlaw anthems to his heartfelt ballads, each track showcases Waylon Jennings’ unique blend of raw authenticity, soulful vocals, and poetic storytelling.

Whether you’re a long-time fan or just getting into Jennings’ music, you’re sure to find something you love in this collection of greatest hits.

So, let’s get started and take a look at the 14 best Waylon Jennings songs of all time.

1. “Brown Eyed Handsome Man”

“Brown Eyed Handsome Man” is a classic song that reflects on the timeless appeal of desiring the unobtainable.

Written and performed by Waylon Jennings, the song has become a cornerstone of classic country music.

With its strong guitar riffs and heartfelt lyrics, the song speaks to the universal themes of love and longing.

The lyrics capture the frustration of wanting something that’s just out of reach, but the music conveys a sense of hope in the face of this unrequited love.

It’s this combination that has made the song so enduringly popular and a true classic of country music.

2. “Will The Wolf Survive?”

“Will the Wolf Survive?” is an iconic song by Waylon Jennings that speaks to the struggles of an individual trying to survive in an ever-changing world.

Written in 1986 and released as a single from his album of the same name, this song speaks to the resilience of individuals in the face of adversity.

The song’s lyrics reflect a universal truth that everyone experiences times of hardship and struggle, yet with resilience, it’s possible to persevere and survive.

Jennings’ song is a reminder that no matter what the odds are, it’s possible to make it through.

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3. “Rainy Day Woman”

Feel the power of resilience with Waylon Jennings’ song “Rainy Day Woman”, a moving anthem that reminds us we can survive and thrive even in the toughest of times.

Released in 1975, the song embodies Jennings’ signature style of country music, with its driving beat and witty lyrics.

The song speaks to the struggles and perseverance of everyday people, urging them to move forward despite the adversity they face.

With an uplifting chorus and an infectious rhythm, “Rainy Day Woman” serves as a powerful reminder of the strength and courage we all possess.

4. “Sweet Dream Woman”

Close your eyes and drift away with Waylon Jennings’ sweet dream of a song “Sweet Dream Woman”.

Written in a minor key, this dreamy tune gives a sense of longing as it tells the story of a man who’s dreaming of a woman who’ll come and save him from his struggles.

The song is a gentle reminder of the hope for a better tomorrow that lies hidden within each of us.

With its warm and comforting melody, “Sweet Dream Woman” is a soothing reminder of the beauty of dreams and the power of hope.

5. “I Ain’t Living Long Like This”

Experience the soulful country croon of Waylon Jennings’ “I Ain’t Living Long Like This” and feel the emotion of his timeless lyrics.

The song, released in 1979, is a melancholic reflection on the fragility of life and the loneliness of living with the knowledge that one day we will all die.

Jennings’ delivery is full of emotion, capturing the sentiment of the lyrics perfectly.

His voice is heartbreaking and his guitar work is impeccable, making this one of his most beloved songs.

6. “Amanda”

Take a moment to appreciate Waylon Jennings’ heartfelt classic, “Amanda”.

The song, written by Bob McDill, is a beautiful tribute to a lost love.

Jennings’ delivery of the tender lyrics is filled with emotion and longing, making it both a classic and a fan favorite.

The song has been covered by many artists throughout the years, showing its timelessness and continued relevance.

“Amanda” is a powerful reminder of what can be achieved through songwriting and vocal performance, and it’s a must-have in any Waylon Jennings greatest hits collection.

7. “The Wurlitzer Prize (I Don’t Want to Get Over You)”

“The Wurlitzer Prize (I Don’t Want to Get Over You)” stands as an esteemed accolade bestowed upon country music’s most exceptional songwriters, celebrating their profound talent and invaluable contributions to the genre.

Renowned as one of his finest creations, this particular song played a pivotal role in catapulting Jennings’ career into the mainstream spotlight, leaving an indelible mark on the music industry.

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Serving as a profound testament to Jennings’ remarkable prowess as both a songwriter and musician, “The Wurlitzer Prize (I Don’t Want to Get Over You)” symbolizes a significant recognition of his exceptional talent, forever solidifying his place in the annals of musical history.

8. “Mental Revenge”

It comes as no surprise that Waylon Jennings’ timeless masterpiece, “Mental Revenge”, strikes a chord with countless listeners.

The song delves deep into the intricate realm of emotions one experiences when wronged by another.

Jennings, through his heartfelt and poetic style, weaves together a composition that etches itself into the memory of all who hear it.

“Mental Revenge” beautifully captures the essence of standing up for oneself, no matter the consequences.

It serves as a powerful reminder of the indomitable spirit that drives us to seek justice, regardless of the personal toll it may exact.

Even today, “Mental Revenge” remains an enduring classic that continues to resonate with listeners across generations.

Its timelessness lies in its ability to evoke profound emotions and connect with the human experience.

9. “Only Daddy That’ll Walk The Line”

Waylon Jennings’ classic hit, “Only Daddy That’ll Walk The Line”, is an anthemic classic that speaks to the power of standing your ground.

It’s a song about a man who won’t be swayed by the surrounding pressures to compromise his values.

The song is a reminder to stay true to oneself, despite the temptations of society, and to never back down in the face of adversity.

With its memorable chorus, catchy guitar riff, and winsome lyrics, it’s no wonder that it has become one of Jennings’ most beloved hits.

10. “Dreaming My Dreams With You”

“Dreaming My Dreams With You”, a cherished composition by Waylon Jennings, radiates with hope and unwavering resolve, leaving an indelible mark on its listeners.

Within the lyrics lies a tapestry of optimism, intertwined with a profound yearning for a place to call home and a brighter tomorrow.

This heartfelt song effortlessly combines a traditional country melody with Jennings’ soul-stirring vocals, culminating in a powerful and deeply resonant experience for all who encounter it.

With its timeless quality, “Dreaming My Dreams With You” is destined to occupy a prominent space among Waylon Jennings’ greatest hits for years to come.

Its impact on audiences is unwavering, its essence transcending time, and its ability to uplift spirits unparalleled.

11. “This Time”

This classic Waylon Jennings tune, “This Time”, is sure to bring a sense of nostalgia and hope to any listener.

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Released as the title track of his 1974, the song has become a signature piece of his career.

Jennings’ emotive vocals give the song a sense of heartache and hope, as he sings of a love that has been lost and found again but may not last.

The song is accompanied by a steady beat and a classic country guitar riff that brings the story to life.

“This Time” is a timeless classic that is sure to make any listener’s heart swell with emotion.

12. “Are You Sure Hank Done It This Way”

You’ll feel like you’ve stepped back in time when you hear “Are You Sure Hank Done It This Way”, Waylon Jennings’ classic hit from the album Dreaming My Dreams.

It’s a tribute to his friend and mentor, Hank Williams, as Jennings sings about the changing times in country music.

Jennings had grown up with the traditional sound of country music, and this song was a way for him to pay homage to the style of music that had made him who he was.

With its catchy chorus and infectious beat, “Are You Sure Hank Done It This Way” was a hit, and it remains a fan favorite today.

13. “I’ve Always Been Crazy”

You may be familiar with Waylon Jennings’ 1975 classic, “Are You Sure Hank Done It This Way”, but one of his most well-known songs is his 1978 single, “I’ve Always Been Crazy”.

This song is a reflection on Waylon’s life and struggles, from his wild days as a young man to his present-day issues with drugs and alcohol.

With its catchy melody and Jennings’ signature twang, “I’ve Always Been Crazy” is an anthem of resilience and determination that has resonated with his fans for decades.

14. “I’m A Ramblin’ Man”

Discover the story of Waylon Jennings, “I’m A Ramblin’ Man”, and find out why it’s become an inspiring anthem for so many.

Written and released in 1974, “I’m A Ramblin’ Man” quickly became one of Waylon Jennings’ most popular songs.

The song tells the story of a man who loves the freedom of the open road and is determined to live his life on his own terms.

The song’s upbeat tempo and classic country sound have made it a favorite of fans of all ages, and it continues to be an inspiring anthem for many.

Best Waylon Jennings Songs – Final Thoughts

With a career spanning over four decades, Waylon Jennings left behind an impressive library of music.

From classics such as “Brown Eyed Handsome Man” to modern hits like “I’m A Ramblin’ Man”, Jennings’ songs have endured the test of time.

Whether you’re a long-time fan or just discovering his music, the 14 greatest hits above are a great starting point to explore and appreciate Jennings’ legacy.

From his outlaw country anthems to his unforgettable ballads, Jennings crafted timeless music that will continue to be enjoyed for generations to come.

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Will Fenton

Introduced to good music at a young age through my father. The first record I remember being played was "Buffalo Soldier" by Bob Marley, I must've been six years old. By the time I was seven, I was taking drum lessons once a week. The challenge but the euphoric feeling of learning a new song was addicting, and I suppose as they say the rest was history. Favorite album of all time? Tattoo You by The Rolling Stones Best gig you've ever been to? Neil Young at Desert Trip in 2016 Media mentions: Evening Standard Daily Mail

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