10 Best Waylon Jennings Songs of All Time

Waylon Jennings, born on June 15, 1937, in Littlefield, Texas, was a seminal figure in country music known for his outlaw image and distinctive, baritone voice. Emerging in the 1960s, Jennings was part of the outlaw country movement, characterized by a rebellious attitude and a departure from the Nashville establishment.

Jennings’ early career saw him working as a bassist for Buddy Holly, narrowly avoiding the tragic plane crash that claimed Holly’s life in 1959. This event profoundly impacted him, shaping his musical direction.

In the 1970s, Jennings rose to prominence with a series of critically acclaimed albums, including “Lonesome, On’ry and Mean” and “Dreaming My Dreams.” His collaborations with Willie Nelson, Johnny Cash, and Kris Kristofferson as part of The Highwaymen further solidified his status as a country music legend.

Notable for his refusal to conform to industry norms, Jennings helped pioneer the “outlaw country” movement. This rebellious stance was reflected in his music, which often featured themes of independence, heartache, and introspection.

Hits like “Good Hearted Woman” and “Mammas Don’t Let Your Babies Grow Up to Be Cowboys” became anthems of the era. Jennings’ influence extended far beyond music, shaping the cultural landscape of country music.

Jennings’ contributions to country music earned him numerous accolades, including Grammy Awards and induction into the Country Music Hall of Fame. His impact is still felt in the genre, as he remains an enduring icon for musicians and fans of authentic, unvarnished country music. Jennings passed away on February 13, 2002, but his legacy lives on through his timeless music.

1. Luckenbach, Texas (Back to the Basics of Love)

The classic tune "Luckenbach, Texas (Back to the Basics of Love)" holds a special place in Waylon Jennings fans' hearts. Why? It has:

• His signature outlaw country sound and twangy guitar riffs.
• A vivid description of leaving the modern world and finding peace in simplicity.
• A catchy chorus: "Let's go to Luckenbach, Texas with Waylon and Willie and the boys."
• References to iconic country music artists like Willie Nelson and Hank Williams.
• The ability to take listeners back to a time where love and music were enough.

Not only that, but it's also a milestone in Jennings' career. It solidified his role as a leader of the outlaw country movement. Its relatable lyrics and infectious melody make it a timeless hit.

Don't miss out on the magic of "Luckenbach, Texas" – listen now and let yourself be taken to a place of simplicity. Join Waylon Jennings on this musical journey that celebrates love, independence, and country music. Embrace the legacy of this song – you won't regret it!

2. Mammas Don't Let Your Babies Grow Up to Be Cowboys

'Mammas Don't Let Your Babies Grow Up to Be Cowboys!' This renowned song by Waylon Jennings spotlights the struggles of leading a cowboy life. Here's a glance at the noteworthy elements of this iconic track:

Adding to its fame, 'Mammas Don't Let Your Babies Grow Up to Be Cowboys' was penned by Ed Bruce. It came out in 1978 as part of the album "Waylon & Willie". This classic country jam occupied the summit of the Billboard Hot Country Songs chart, making its mark in music history.

These facts give you a clearer idea of 'Mammas Don't Let Your Babies Grow Up to Be Cowboys' by Waylon Jennings. Its magical lyrics and success make it an unforgettable contribution to Waylon's portfolio.

3. I've Always Been Crazy

Waylon Jennings' "I've Always Been Crazy" is a remarkable gem among his many songs. It's a true outlaw country track, revealing Jennings' rebellious nature and self-expression.

The song captures the essence of Jennings' artistic persona. His honest lyrics explore the inner turmoil of a man who won't conform to society. His powerful vocals and electrifying guitar riffs create a unique sound, and his passionate delivery builds a connection with listeners.

"I've Always Been Crazy" was an anthem for those who embraced their individuality. It resonated with people who felt like outsiders, providing a sense of belonging in Jennings' music community. This hit solidified its status as a standout masterpiece in his catalog.

Jennings wrote this song during a difficult time in his life. He battled personal demons and faced legal troubles, but he used this song as catharsis. Remarkably, it became a chart-topper and served as an emblem of Jennings' resilience and talent. So, let "I've Always Been Crazy" be a reminder that Hank didn't do it this way, Waylon did it his own badass way.

4. Are You Sure Hank Done It This Way

Are You Sure Hank Did It This Way? A classic Waylon Jennings tune. It questions if one is really following in Hank Williams' footsteps.

Analysis:

• How Hank did it? His own, pioneering style.
• Do all artists follow him? Not necessarily.
• Is there a 'right' way? Maybe, but some opt for their own.
• Legacy of Hank Williams? He set the bar high for country music.

Fun Fact: Not only does the song honor Hank Williams, it also critiques the surge of mainstream country music during that time.

If Waylon's voice doesn't please you, you should get your ears checked!

5. Just to Satisfy You

Waylon Jennings' "Just to Satisfy You" is one of his most popular songs. It's a soulful and heartfelt tune that conveys love and desire. Let's take a closer look at it:

Jennings' voice and words make this song captivating. Plus, the guitar solos give it a special feel. Get ready to feel the thrill! Not living long like this, but it'll be worth it with Waylon Jennings!

6. I Ain't Living Long Like This

Waylon Jennings' "I Ain't Living Long Like This" is renowned for its unique lyrics and remarkable melody. Let's explore this timeless piece!

The catchy beat and gripping storytelling take listeners on a journey through an outlaw's life.

Jennings' soulful vocals and masterful guitar work set the song apart. The lyrics address rebellion, freedom, and living on the edge.

The exceptional production quality creates a rich tapestry of sound. Listen closely to Jennings' vocal delivery and guitar solos for a truly immersive experience.

Love can be sweet or bitter, just like this song.

7. Amanda

Amanda – Waylon Jennings' masterpiece! It captures a lost love's essence and bittersweet memories. Jennings takes us on an emotional journey through lyrics and melodies. Its relatability and depth make it timeless. Its popularity proves Jennings' talent.

Let's take a closer look.

Lyrics: Poignant lines like "I've held it all inward, God knows I've tried / But it's an awful awakening in a country boy's life." Paint a picture of heartache and longing.

Vocals: Jennings' warm, rich voice adds emotion. His delivery is honest and vulnerable.

Instrumentation: Acoustic guitar, piano and strings blend together. The melody complements the lyrics, creating a captivating experience.

Don't miss out on Amanda! It's among Jennings' finest works. Let the lyrics and melody transport you and touch your heart.

8. Only Daddy That'll Walk the Line

Waylon Jennings' "Only Daddy That'll Walk the Line" is a classic. It displays his unique sound and storytelling. It was released in November 1968.

Genre: Country, Outlaw Country. Songwriters: Ivy J. Bryant.

Listen to Waylon's passionate and raw vocals. It is an amazing song that captures the essence of his artistry. For good-hearted women, Waylon's song will have you grabbing a cold beer and a broken heart.

9. Good Hearted Woman

A classic country song, "Good Hearted Woman" perfectly captures the essence of Waylon Jennings' gritty and honest style. Its unforgettable melody and heartfelt lyrics showcase Jennings' storytelling ability.

Verse 1: Dreams that were forgotten, the good life he promised.

Chorus: She's a good-hearted woman in love with a good-timin' man. She loves him despite not understanding his ways. Through laughter and tears, they'll pass through this world hand in hand.

"Good Hearted Woman" takes listeners on an emotional journey through love, heartbreak, and complicated relationships. Jennings' raw vocals connect with the audience.

Willie Nelson co-wrote this powerful and iconic song with Jennings. Get ready to hear some twangin' country music from Waylon! It'll make you reminisce about the past, with fast cars and fast country music.

10. Theme From The Dukes Of Hazzard

The song "Theme From The Dukes Of Hazzard" by Waylon Jennings is a standout amongst his best songs. It has a catchy melody and is connected to a popular TV show. Here are the details:

• Release Year – 1979
• Genre – Country
• Chart Performance – Reached #1 on Billboard Hot Country Songs chart
• Awards – Nominated for a Grammy Award for Best Country Vocal Performance, Male in 1981

This song has a special place in fans' hearts due to its adventurous spirit. If you want to explore Waylon Jennings' music, here are some recommendations:

1. "Good Hearted Woman" – A classic country duet with Willie Nelson.
2. "Mammas Don't Let Your Babies Grow Up to Be Cowboys" – A timeless anthem.
3. "I've Always Been Crazy" – An introspective and autobiographical song.
4. "Are You Sure Hank Done It This Way?" – A rebellious and honest track.

By listening to these songs, you'll gain an appreciation for Jennings' contributions to the country music landscape. Each song embodies his unique style, combining traditional country with outlaw elements. So, go ahead and start this musical journey!

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.