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Home Best Songs Guide

10 Best Waylon Jennings Songs of All Time

List of the Top 10 Best Waylon Jennings Songs of All Time

Edward Tomlin by Edward Tomlin
November 28, 2023
in Best Songs Guide
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10 Best Waylon Jennings Songs of All Time
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Waylon Jennings, born on June 15, 1937, in Littlefield, Texas, was a country music outlaw whose impact on the genre is immeasurable. Emerging in the 1960s, Jennings challenged the polished Nashville sound, forging a gritty, rebellious style that came to define outlaw country.

A skilled guitarist and distinctive vocalist, Waylon Jennings rose to prominence with hits like “Lonesome, On’ry and Mean” and “This Time.” His refusal to conform to industry norms led to the formation of the “Outlaw” movement in the 1970s, alongside Willie Nelson, Merle Haggard, and others. This rebellion represented a departure from the polished country-pop sound, embracing a raw, rootsy authenticity.

The landmark album “Wanted! The Outlaws” (1976), featuring Jennings, Willie Nelson, Tompall Glaser, and Jessi Colter, became the first country album to achieve platinum status. Jennings’ “Are You Sure Hank Done It This Way” and “Mammas Don’t Let Your Babies Grow Up to Be Cowboys” further solidified his status as a country music icon.

Beyond his musical contributions, Waylon Jennings was known for his assertive personality, signature style with a black hat and leather vest, and a reputation for living life on his terms. His influence on country music endures, as he remains a symbol of artistic independence and the embodiment of outlaw spirit within the genre. Jennings passed away on February 13, 2002, leaving behind a legacy that continues to shape the landscape of country music.

Table of Contents

  • 1. Luckenbach, Texas (Back to the Basics of Love)
  • 2. Mamas Don't Let Your Babies Grow Up to Be Cowboys
  • 3. Good-Hearted Woman
  • 4. Are You Sure Hank Done It This Way
  • 5. I've Always Been Crazy
  • 6. Amanda
  • 7. Honky Tonk Heroes
  • 8. I Ain't Living Long Like This
  • 9. Only Daddy That'll Walk the Line
  • 10. Dreaming My Dreams with You

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

"Luckenbach, Texas (Back to the Basics of Love)" is a country music classic. Its catchy melody and heartfelt lyrics capture the simple life when love was all that mattered. It encourages us to prioritize love over material wealth. It's historical significance sparked a renewed interest in the tiny Texas Hill Country town it's named after.

Your mama may not have wanted you to be a cowboy, but you can still enjoy this song about a wild and free life! Its message of true happiness and fulfillment through simplicity will leave an indelible mark on your heart.

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

"Mamas Don't Let Your Babies Grow Up to Be Cowboys" – that's the title of Waylon Jennings' iconic tune. It became an instant hit in 1978, topping the charts with its catchy melody and relatable lyrics.

Willie Nelson joined Waylon to create a powerful duet. They showed off their distinctive voices and harmonies!

The song carries a timeless message of caution. It speaks of the hardships of being a cowboy, and encourages parents to guide their children towards other careers.

It's a mix of country and western sounds, with an upbeat rhythm and lively instrumentation. It has had a lasting impact on popular culture, appearing in films, TV shows and even advertisements.

"Mamas Don't Let Your Babies Grow Up to Be Cowboys" is a reminder of the influence parents have over their kids. They can help them avoid potential hardships by choosing different paths.

3. Good-Hearted Woman

Waylon Jennings' "Good-Hearted Woman" is a renowned song. It features his unique musical style and impressive lyricism. It captures the essence of a kind-hearted woman – her virtues and endearing qualities.

Released in 1971, it was included in the album "Honky Tonk Heroes". It's a country song, 2:54 minutes long.

The lyrics showcase Waylon's storytelling talent. They explore the complexities of love and devotion, so are relatable to many.

I recall listening to this classic track on road trips with friends. Its timeless appeal always sparks nostalgia and creates a shared atmosphere of memories and joy during the journey. Good-Hearted Woman has a special place in my heart as it displays Waylon Jennings' remarkable artistry and lasting legacy. Are You Sure Hank Done It This Way? Well, Waylon certainly did it his own damn way.

4. Are You Sure Hank Done It This Way

 

"Are You Sure Hank Done It This Way?" is a classic Waylon Jennings song, questioning if Hank Williams did things the traditional way. Let's explore this influential track and its effects on the music industry.

Column 1: Song Column 2: Album Column 3: Release Year

  1. Are You Sure Hank Done It This Way?
    Dreaming My Dreams – 1975

This energizing and rebellious tune displays Jennings' special voice and meaningful lyrics. It questions the accepted customs of country music, making it stand out in his discography.

It's important to understand that Jennings was a pioneer in the Outlaw Country movement. This subgenre pushed against mainstream country music, introducing a grittier sound and more rebellious themes.

Don't miss out on this classic tune! Appreciate Jennings' unique contribution and comprehend how he reshaped the genre.

Experience the spirit of Waylon Jennings by tuning into this timeless song. Rediscover his unmatched talent and embrace a piece of music history that still resonates with audiences around the world.

"Folks call me crazy, but I'm just being me like Waylon Jennings."

5. I've Always Been Crazy

Waylon Jennings' "I've Always Been Crazy" is an iconic song. It shows his rebellious side and fearless attitude. Raw emotions and lyrics draw listeners in. It's autobiographical, based on his life.

An interesting tidbit, during one live performance, Waylon took a moment to thank his critics. He said their doubts and skeptics fueled his passion for music.

Another song of his that's worth mentioning is "Amanda". He wrote a ballad dedicated to a woman with that name. But, he didn't call it "Crazy Chihuahua"!

6. Amanda

"Amanda" is a timeless classic that sits in sixth place on our list of the best Waylon Jennings songs. It has all the hallmarks of Jennings' exceptional storytelling – evoking deep emotions, a distinctive baritone, a universal melody, and a yearning devotion. This song also exemplifies Jennings' ability to bring traditional country sounds to a modern edge.

A captivating story is linked to "Amanda". It is said that Waylon was inspired to record this track after meeting a woman called Amanda at one of his concerts. They had an instant connection and her name was etched in his memory. This spurred him to bring Bob McDill's composition to life.

The intense emotion and lasting appeal of "Amanda" has made it a standout in Jennings' impressive catalog of hits. It continues to live on in the hearts of Waylon Jennings' fans.

7. Honky Tonk Heroes

Waylon Jennings' "Honky Tonk Heroes" is a captivating song! It displays his unique talent and contribution to country music. Here's the skinny:

Released in 1973, it was on the album of the same name. Genre? Country. Length? 3:29. Songwriter(s)? Billy Joe Shaver.

This classic tune is all about Jennings' rebellious spirit and real-talk storytelling. Its catchy melodies and heartfelt lyrics make it an anthem for all who find solace in the honky-tonk lifestyle.

But there's more to the story! In 1972, Shaver approached Jennings with a stack of self-penned songs. Record execs were skeptical. However, Jennings heard the authenticity and power of Shaver's words. They put together an album that would forever change the country music scene.

8. I Ain't Living Long Like This

' Waylon Jennings' "I Ain't Living Long Like This" is an awe-inspiring song! It displays his unique style and talent with its captivating lyrics talking of battles and standing up to society's demands.

Get a gist of this magical track with the following table:

Song Artist Year
I Ain't Living Long Like This Waylon Jennings 1979

Not only is the melody and its words timeless, but it stands out for its gripping guitar licks and soulful vocals. This rebellious song touches listeners, which is why it's a fan favorite among Waylon Jennings' works.

An interesting detail is that this song was initially written and recorded by Rodney Crowell in 1978. Later on, Waylon Jennings covered it for his 1979 album of the same name, which became one of his most successful albums.'

9. Only Daddy That'll Walk the Line

"Only Daddy That'll Walk the Line" is a classic song by Waylon Jennings. He blended country and rock music in this 1968 hit. It became popular on both the country and pop charts.

This song reflects Jennings' independent spirit and refusal to conform. Lyrics show his rebellious persona, which resonates with his fans.

Here are the elements of this track:

Only Daddy That'll Walk the Line
Artist Waylon Jennings
Release Year 1968
Genre Country/Rock

Jimmy Bryant wrote this iconic song. It quickly gained fame and became one of Waylon's signature tunes. It helped him gain mainstream recognition in the music industry.

Dreaming of Waylon's voice and lyrics is a dream I never want to end.

10. Dreaming My Dreams with You

 

Waylon Jennings' classic song 'Dreaming My Dreams with You' has touched the hearts of millions. With its touching lyrics and melodious tune, this song has become an evergreen in country music.

Here are some facts about 'Dreaming My Dreams with You':

Year Released Album Chart Peak Position
1975 Dreaming My Dreams #10

This song is significant in Jennings' discography, as it reached number 10 on the charts when it came out in 1975. The album 'Dreaming My Dreams' displayed Jennings' storytelling skills and made him a country music icon.

To experience the essence of 'Dreaming My Dreams with You', we must explore its emotional depths. The lyrics tell a story of longing for a lost love, creating a feeling of nostalgia. Jennings' voice adds to the vulnerability, making the song truly resonate with listeners.

Don't miss 'Dreaming My Dreams with You'. Take a journey back in time and get lost in this masterpiece. Let the song take you to a place where emotions run deep and melodies linger in your heart.

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.

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