Celebrate the Heart of Country, Americana, and Roots Music!

Drop Us A Line, Y'all

Y'all interested in advertising, partnering up, contributing stories, joining our team, or just got a question? Well, don't be shy, drop us a line!

Follow Us

Blast From The Past: Waylon Jennings’ Exciting Career as the Legendary Outlaw

by
  • Arden is a Senior Country Music Journalist for Country Thang Daily, specializing in classic hits and contemporary chart-toppers.
  • Prior to joining Country Thang Daily, Arden wrote for Billboard and People magazine, covering country music legends and emerging artists.
  • Arden holds a Bachelor of Arts in Journalism from the University of Tennessee, with a minor in Music Studies.

At the very young age of twelve-years-old, Waylon Arnold Jennings started his road to fame. As a young boy, Jennings was already chasing his dreams, and nothing could get in his way. He scored a time spot on a Texas radio station, formed a band, and the rest is history! What he did not know back then is that he would become what some fans consider, a country music pioneer.

Let’s take a look back at the colorful career of the legendary Waylon Jennings.

How Did It All Started For the Country Legend

Born on June 15, 1937 to Lorene and William Jennings, the country singer was a mixture of Cherokee, Irish, and Dutch, with the original name of “Wayland” – which means land by the highway. Later on, his name was changed to Waylon, but not by his choice. In his autobiography, Waylon said, “I didn’t like Waylon. It sounded corny and hillbilly, but it’s been good to me, and I’m pretty well at peace with it right now.”

In 1958, Jennings got his first big break after some time creating jingles for the radio station. He was enlisted to tour with Buddy Holly and started his own climb to fame. But in an unfortunate event, Holly died in a plane crash where Jennings gave up his seat for what was supposed to be a flight to their next tour stop. That day would later become known as “The Day the Music Died,” but Jennings and his music were given a chance to live.

Jennings revealed the painful grief he felt following the deadly plane crash. “God Almighty, for years I thought I caused it,” he said. “I was just trying to figure out what to do with myself, you know? I was a completely changed person. I quit for a while—I wouldn’t even play a guitar, I wouldn’t pick it up.” Luckily, he found his way back to his love of music and moved forward with a new brand of tune.

The Momentum of Waylon Jennings’ Career Began 

Waylon Jennings’ career finally kicked off in the 1970s when he joined what was known as the outlaw movement in country music. The movement formed in opposition to the Nashville sound style, which tried to diminish the honky-tonk influences of older country music. 

Jennings joined the ranks of fellow outlaws and big country stars such as Merle Haggard, Hank Williams Jr., and Willie Nelson. They’ve released an endless number of hit singles and albums.

In the mid-1980s, Jennings and Nelson teamed up with Kris Kristofferson and Johnny Cash to form the country supergroup The Highwaymen. Through the course of their ten years together, the group successfully released a total of three studio albums and had three singles that made their way onto the charts, including the No. 1 hit, “Highwayman.”

In addition to his highly successful music career, Jennings also appeared in movies and on television. Indeed, his powerful voice, edgy sound, and no-nonsense personality made him the big star he is today.

His Music And Legacy Keep Moving Forward

During his career, Jennings had fifty-four albums chart, with eleven of them reaching No. 1. He also influenced many country music artists, including Hank Williams Jr. and Travis Tritt. 

However, Jennings began to experience increased issues with diabetes that limited his mobility and kept him away from performing as much as he wanted. Jennings’ diabetes went on to worsen over the course of the next two years.

In 2002, Jennings died in his sleep due to complications with diabetes at the age of sixty-four. However, his music and legacy continue to move forward and influence many. He is missed dearly and will forever remain a country music idol!

Check out at some of Waylon Jennings’ best songs and performances below!

https://www.youtube.com/watch?v=skh-Bv_vVC8

Trending

Latest Stories

Craig Morgan delivering an emotional performance of 'The Father, My Son, and the Holy Ghost' on The Kelly Clarkson Show, moving the audience to tears as he honors his son's memory.

Craig Morgan’s “The Father, My Son, and the Holy Ghost” Moves “The Kelly Clarkson Show” to Tears

In 2016, Craig Morgan faced a tragedy no parent should ever endure: the loss of his 19-year-old son, Jerry, in a tubing accident on Kentucky Lake. Morgan’s heartbreak was profound, ...

Jesse Keith Whitley and his son Jackie performing a heartfelt duet of 'Don't Close Your Eyes,' honoring Keith Whitley's legacy with a touching family tribute.

Jesse Keith Whitley and Son Jackie Duet “Don’t Close Your Eyes” in a Heartfelt Tribute

At Lorrie Morgan’s Spicy Hot Chicken Coop in Panama City Beach, Florida, fans were treated to a magical evening when Jesse Keith Whitley performed his father’s iconic song “Don’t Close ...

Patsy Cline and Willie Nelson brought together through modern technology for a duet of 'Just a Closer Walk with Thee,' blending their iconic voices in a timeless gospel masterpiece.

Willie Nelson Joins Patsy Cline for a Heavenly “Just a Closer Walk with Thee”

Patsy Cline’s tragic death in a 1963 plane crash left an irreplaceable void in country music. Her haunting voice, which gave us classics like “Cr𝐚zy” and “I Fall to Pieces,” ...

Vince Gill performing 'The Price of Regret,' conveying a heartfelt message of unity, compassion, and healing, showcasing his enduring impact on country music.

Vince Gill’s “The Price of Regret” Is a Timeless Call for Unity

In 2019, Vince Gill once again proved why he’s a cornerstone of country music with his powerful single “The Price of Regret” from the album Okie. Known for his ability ...

George Jones delivering his final performance of 'He Stopped Loving Her Today' in 2013, a heartfelt farewell from a country music legend filled with raw emotion.

George Jones’ Last Performance of “He Stopped Loving Her Today” Was Unforgettable

George Jones, lovingly known as “The Possum,” gave the world one last gift with his final performance of “He Stopped Loving Her Today” on April 6, 2013. Captured during his ...

Blake Shelton performing a lively cover of 'Footloose,' inspiring Texas Roadhouse staff to create a viral line dance that blends music, fun, and energetic dining vibes.

Texas Roadhouse Staff Goes Viral Dancing to Blake Shelton’s “Footloose”

In 2015, Texas Roadhouse became more than just a restaurant serving mouthwatering steaks and buttery rolls—it became the stage for a viral moment with everyone tapping their feet. The reason? ...

George Jones and Dolly Parton’s Breathtaking Duet of “The Blues Man”

In 2005, country legends George Jones and Dolly Parton teamed up for a stunning rendition of Hank Williams Jr.’s “The Blues Man.” The collaboration marked the first time these two ...

Scotty McCreery Stuns With “That’s All Right, Mama” on American Idol

In 2011, a skinny, baseball-loving teen from North Carolina stepped onto the American Idol stage and turned the country music world on its ear. Chris Piner of American Songwriter recalls ...

Scotty McCreery performing 'Hello Darlin'' at the Grand Ole Opry in 2015, paying tribute to Conway Twitty and honoring the roots of country music.

Scotty McCreery Honors Conway Twitty with Moving “Hello Darlin'” at the Opry

In 2015, Scotty McCreery stepped onto the Grand Ole Opry stage with a reverence few performers could match. Four years after his American Idol win, McCreery proved he wasn’t just ...

Alex Miller performing on stage with his signature cowboy hat, showcasing his classic country charm and journey from American Idol to the Grand Ole Opry.

Alex Miller’s “Silver Wings” Performance Earns Grand Ole Opry Invite

For many artists, the Grand Ole Opry is a stage where dreams are made. It’s where legends are born and where country music’s history comes alive. For Alex Miller, a ...