Waylon Jennings – Nashville Rebel

“Waylon Jennings was an American archetype, the bad guy with the big heart”

  • Kris Kristofferson

I was moved to write an article on Waylon Jennings after listening to Shannon McNally’s fine – and very ambitious – CD, The Waylon Sessions. (A recording that reinforced just how truly fearless McNally is).

I’ve been a casual Waylon fan since a hometown friend introduced me to him and the classic 1973 album Honky Tonk Heroes back in the day. At that time I was – and still am – heavily into Blues and R&B but open enough to be taken by the sound of the overall recording and that unmistakable voice that could only be Waylon Jennings. Additionally, the liner notes underlined the gravity of the whole affair when noted that the prime songwriter Billy Joe Shaver threatened to fight Jennings because “he was messin’ with my melody”. Knowing more about Jennings today that just all seems so fitting, and in keeping with the tough imposing image put forward by Waylon Jennings.

That threatening persona was no doubt amplified by Jennings being viewed as the high profile leader of the Outlaw movement. The Outlaw phenomenon – exemplifying a hard living lifestyle – was a Nashville marketing strategy, and, as laid out for public consumption it was, for the most part, independent of Jennings. The legitimate Outlaw stance, as spearheaded by Jennings, can be found in the backstory of Jennings rebelling against the Nashville establishment’s business practices. Jennings was characterized as an outlaw in Nashville because he wanted artistic freedom. Specifically, the crux of the matter is that Waylon insisted on having the right to record material that he wanted to record while employing songwriters and musicians of his choosing. (The musicians in question being his road band, The Waylors, instead of the regular Nashville session players; and the songwriters being those other than the Nashville staff or established songwriters). As a backdrop, it should be taken into account that Rock stars had benefitted from those same “indulgences” for years. To Jennings’ credit, in fighting the accepted style and approach of the sterile Nashville Sound, he changed the way things were done in Music City forever. And, other Country stars – initially in the likes of Willie Nelson and Kris Kristofferson – followed suit.

In sum, rather than trying to destroy the system, his actions displayed the steadfastness of a strong willed Jennings wanting to do music his way. It was a tendency that spoke more of the self-reliance that was evident some years previous, going back to the start of his career. That beginning for Waylon was as a teenage DJ and musician in his Texas hometown of Littlefield, located about 25 miles south of Lubbock.  

Waylon Arnold Jennings, (June 15, 1937 – February 13, 2002), began his life and career in Littlefield, and, along with his parents and three younger brothers, worked the cotton fields of the family farm. Like many families in West Texas the Jennings knew only an impoverished existence. Although the parents may have known differently, the four boys’ outlook on life was that everyone, black and white, was as poor as they were. The situation left a lasting impression on Waylon and shaped his view on race relations. On reflection, later in life, Waylon would say: “There was just no difference in a poor country boy and black people in my mind. I worked the fields with black people and never paid much attention to it.”

The Jennings household was a musical one in that the family gathered around the radio regularly to listen to The Grand Ole Opry and The Louisiana Hayride and both parents were accomplished guitar pickers. Of the four boys it was Waylon for whom the music flame burned the brightest. Waylon’s mother taught him the basics of guitar when he was 8 years old and Waylon said of his father: “My dad played like Jimmie Rodgers. And we’d sit around and sing his songs when I was a kid”. Young Waylon was a devotee of Hank Williams and Ernest Tubb and cited influences including Bob Wills, Floyd Tillman, Carl Smith, and Elvis Presley.

As a young preteen Waylon worked as a DJ both in Littlefield as well as in Lubbock. At 13, performing for the first time, Jennings won first prize at a jamboree sponsored by local radio station KSEL. By the time he was 14 Waylon was a known commodity at regional talent shows playing guitar and singing a mix of Country and Pop tunes. Waylon left high school at 16 to pursue a career in music, continuing to both DJ as well as perform in venues and on the radio with his first band The Texas Longhorns.

While working as a DJ for KLLL in Lubbock in 1958, Waylon struck up a friendship with native son Buddy Holly. They became close with Holly mentoring Waylon and arranging for his first recording session. The resultant single, “Jole Blon”, a traditional Cajun waltz, often called “the Cajun national anthem” failed to make any noise but it forged the start of the Holly / Jennings story. (Incidentally, Jennings couldn’t understand the Louisiana patois of the recording that he used to learn the song, so he sang the song phonetically).

Holly, had who had recently disbanded the first incarnation of The Crickets, convinced Waylon to come aboard as the bass player of the newly formed Crickets. Waylon, displaying only rudimentary bass skills at the outset, would go on to play with Holly for 2 years (1958-59). The end would come with the ill-fated 1959 Winter Dance Party tour and plane crash that would take the lives of Buddy Holly as well as Ritchie Valens and J.P. “The Big Bopper” Richardson. The three fell prey to bad weather and, complicating matters, an inexperienced pilot.

There are conflicting stories as to who was supposed to occupy the 3 available seats on the chartered plane that was to travel some 365 miles from Clear Lake Iowa to Moorhead Minnesota in the early hours of February 3, 1959. Suffice to say that Waylon and fellow bandmates, Tommy Allsup and Carl Bunch, were not on the plane, and made the trip in the rundown tour bus used to transport them as well as the others on the bill: Dion & The Belmonts and Frankie Sardo.

Before take-off Holly and Jennings were cracking wise with each other with Holly saying “I hope your bus freezes up again” and Waylon responding with “Well, I hope your ol’ plane crashes”. Those words would come back to haunt Waylon who, racked with survivor’s guilt, completed the tour and then headed back to Lubbock with “no intention of playing another note.”

Once back in Texas he returned to working as a DJ and it wasn’t until a year later in 1960 that he moved to Phoenix Arizona and restarted his musical career. He soon formed The Waylors playing a number of clubs in Arizona before he developed a huge local following as the house band at JD’s, a club in Scottsdale. That led him to recording a few singles for Trend, a minor Arizona based label. Although not generating much in actual sales, those singles combined with his JD’s following brought Waylon to the attention of Herb Alpert and Jerry Moss at A&M Records who signed him to a contract in 1963, prompting a move to the City of Angels.

The Jennings / A&M union was short lived however. An apparent difference of opinion surfaced when A&M – with their view of Waylon being more Folk than Country – planned to steer him in a Folk / Pop direction. When subsequent recordings tanked, Waylon asked for his release. (Waylon summed up his A&M experience by saying that Alpert and Moss wanted him “to sound like Al Martino and I wanted to sound like Flatt and Scruggs.”)

Waylon’s next course of action would serve to establish him as a prominent recording and performing artist, and – aided by his Outlaw persona – cement his position as a Country superstar. It all started when, on the recommendation of a number of people including Bobby Bare and Willie Nelson, Waylon was signed to RCA by then talent scout, producer, and VP of RCA’s Country Division Chet Atkins. The Jennings / RCA partnership would last for 20 years including 5 years – 1965 to 1970 – with Atkins producing Waylon’s recordings.

*(An interesting Nashville sidebar. When Waylon moved there in 1965 he made the acquaintance of Johnny Cash, and for a time, the future lifelong friends, were roommates in Music City. Jennings would later comment that he and Johnny were “the original odd couple” with an agreement that Waylon would do the cleaning and Cash the cooking. Waylon didn’t think too much of Cash’s culinary skills other than to say “he could put together a breakfast.”

And, without dwelling on the topic, Jennings and Cash both ingested amphetamines by the handful. Waylon, providing perspective, noted that “pills were the artificial energy on which Nashville ran around the clock and then some”. Drug dependency would play a role in Waylon’s life going forward.)*

Starting with his first RCA album Folk Country, a 1966 release, Waylon went on to record 9 more albums under Chet Atkins’ supervision. And, by 1968 Waylon had several hit singles including the first one out of the gate in 1965: “Stop The World (And Let Me Off)” that was a Top 20 Country single. Other notable singles in that time period include “Walk On Out Of My Mind” (1967, #5 Country), “The Chokin’ Kind” (1967, #8 Country), and “Only Daddy That’ll Walk The Line” (1968, #2 Country).

Also, in that time frame, Waylon starred in the 1966 movie “Nashville Rebel” handling both acting and performance roles. And, Jennings – who in the course of his career would win 2 Grammys and score 13 nominations – won his first Grammy in 1967 for his recording of “MacArthur Park”, (shared with the The Kimberlys vocal group).

Chet Atkins, for his part, played a major role in Waylon’s early success. That is, Atkins, who is credited with establishing the Pop heavy Nashville sound, produced a string of hits, and was responsible for maintaining RCA and Nashville’s prominent profile in Country Music. Waylon chafed under Chet Atkins’ studio direction because Waylon plainly wanted to play music as he felt it. As he said: “Some people have their music. My music is me”. While at odds musically with Atkins, Waylon respected him, and understood that Atkins had to serve what he viewed to be RCA’s best interests. In addition, Jennings acknowledged that his drug using lifestyle – that didn’t coincide with the straight edged Atkins’ view on life – may have played a role in their relationship. Waylon summed it up this way: “The guy the drunk man hates the most is a sober man”.

By the start of the 70’s Waylon started to assert himself. When he felt he was being frozen out by Nashville’s mainstream, he responded by hiring Neil Reshon, Miles Davis’ eccentric NYC based manager. Reshon was instrumental in Waylon broadening his audience appeal by getting him into high profile venues like Max’s Kansas City, a New York City spot usually reserved for Rock acts. And, in 1972, most importantly from Waylon’s perspective, when it was time to renew his RCA contract, Reshon helped him gain artistic control of his recordings going forward. From there Waylon started putting his own spin on hard core Country songs of heartbreak, bad breaks, and difficult choices. He did so by incorporating accepted Country instrumentation, and merging Folk’s introspective lyrics with Rock’s rhythms on a tougher more bass driven sound.

With artistic freedom assured, Waylon’s first statement, Honky Tonk Heroes, stands with his best recordings. “Heroes” marked a distinct departure from the slick production of traditional Country music. Backed by The Waylors and choice studio musicians, (including guitar players Eddie Hinton and Reggie Young usually associated with Southern Soul), Waylon displays a fresh urgency and excitement on 10 songs. There isn’t a weak cut on the album; highlights include the title song plus other gems like “Omaha”, and “Black Rose”; (with the fitting lyrics: “The Devil made me do it the first time / The second time I did it on my own / Lord, put a handle on a simple handed man / And help me leave that black rose alone”).

Honky Tonk Heroes started a trend of a number of commercially and critically acclaimed releases including the highly regarded follow-up, This Time, that contains Waylon’s first #1 Country hit of the same name. Following are some highlights of the remainder of Waylon’s 45 studio albums (with 20 of them landing in the Top 10). It should also be kept in mind that the total of 60 albums that Waylon recorded over a 50 year career contained an impressive 16 #1 Country singles.

1967 Love Of The Common People

  • A foreshadowing of Waylon coming into his own
  • Includes the hits “The Chokin Kind” and “Walk On Out Of My Mind”

1971 The Taker / Tulsa

  • Waylon’s first post Chet Atkins release
  • It’s a sampling of Waylon welcoming new songwriters to Nashville with the album featuring four songs by Kris Kristofferson
  • Includes “Lovin’ Her Was (Easier Than Anything I’ve Ever Done)”, “Sunday Morning Comin’ Down”, and “The Taker” – all written by Kristofferson

1973 Lonesome On’ry And Mean

  • The first album unfettered by the clutches of old school Nashville
  • Backed by The Waylors; produced by Waylon
  • Includes the title cut and outstanding covers of Danny O’Keefe’s “Good Time Charlie’s Got The Blues” and Kristofferson’s “Me And Bobby McGee”

1974 This Time

  • The follow-up to Honky Tonk Heroes
  • The title song was Waylon’s first #1 hit
  • Includes 4 Willie Nelson songs and the fine Buddy Holly Medley: “Well Alright / It’s So Easy/ Maybe Baby / Peggy Sue”

1974 The Ramblin’ Man

  • The album personifies Waylon’s Outlaw image
  • Waylon’s first #1 hit album
  • Top songs include “I’m A Ramblin’ Man”, the exquisite “Amanda”, “Oklahoma Sunshine”, and “Memories of You And I”

1975 Dreamin’ My Dreams

  • Another #1 album
  • Hailed by many critics as Waylon’s finest release; and Waylon as “my favourite album I’ve ever done”
  • Produced by Waylon and singer songwriter and ex Sun Records producer “Cowboy” Jack Clement who Waylon likened in approach to Buddy Holly: “Like Buddy, Jack was another guy going after the feel”.
  • Includes “Are You Sure Hank Done It This Way”, “Waymore’s Blues”, and “Bob Wills Is Still The King”
  • “Are You Sure Hank Done It This Way” was Waylon’s first crossover hit

Honourable Mentions (not original studio recordings as such in that they’re compilations, but included here because of their huge impact on Country Music in general):

1976 Wanted! Outlaws

  • Actually a compilation of previously released material
  • The first Country album to be certified Platinum
  • Features Willie Nelson, Tompall Glaser, and Jessi Colter; (the release furthered all of their careers; Waylon’s participation significantly enhanced his reputation as a central figure of Outlaw Country and a major Country star)
  • Includes the Grammy nominated Jennings / Colter duet “Suspicious Minds”
  • A prime marketing vehicle in RCA’s promotion of the Outlaw mystique

1979 Greatest Hits

  • A compilation of 9 outstanding tracks
  • Not a comprehensive set but it stands as a snapshot of Waylon’s prominent role in the Outlaw phenomenon
  • Included here on the basis of the impressive 4 million copies sold – unprecedented in Country music at the time

Once again the list as cited stands as highlights of Waylon’s recording career. There are other releases – with more than 35 more studio albums to choose from – that are worthy of being on the list but these provide an even-handed cross section of Waylon’s works.

Waylon continued his maverick / Outlaw ways – at odds with the industry while touring extensively and remaining a major draw even when the hits dried up as the 80’s drew to a close. He often refused to attend music awards shows reasoning that artists shouldn’t be competing against each other. Instead his feeling was that those shows should exist solely as a celebration of the art itself. In fact, Waylon was the only living entertainer who ever refused to show up at his own induction into the Country Music Hall Of Fame in Nashville in 2001. (He sent his son Shooter to accept on his behalf).

Amidst all of the above Waylon continued in the spotlight. He won his second Grammy Award for his duet with Willie Nelson on the classic “Mamas Don’t Let Your Babies Grow Up to Be Cowboys”. (The single was taken from the multimillion selling album Waylon & Willie). And he followed that up with 2 Grammy nominated albums with The Highwaymen (with Nelson, Cash, and Kristofferson).

Representative of his mainstream appeal, Waylon appeared on TV shows such as “Sesame Street” and narrated “The Dukes Of Hazard” as well as writing and recording the theme song “Good ‘Ol Boys”. All of this and more was captured in his highly regarded 1996 autobiography Waylon, The Life Story Of Waylon Jennings (co-authored with guitarist and writer Lenny Kaye).

The “more” includes his 21 year addiction to amphetamines and cocaine that he quit cold turkey in the mid 80’s when he came to the realization of how it affected those close to him – especially his wife Jessi Colter and son Shooter. Although he was able to shake his substance abuse he still endured associated heart and diabetes troubles. Resultant surgeries and a desire to spend more time with his family led Waylon to quit touring in 1997.

Waylon Jennings died in his sleep at home in Chandler Arizona on February 13, 2002, Cause of death was attributed to a heart attack.

Waylon Jennings was a towering figure in Country Music. While maintaining an acrimonious relationship with the Country Music establishment till the end, he continued to be loved by his many fans and held in high regard by his peers.

“I loved Waylon. He had a great voice and a way with a song like no one else. He was a class act as an artist and a man; I’m really going to miss him”.

  • Emmylou Harris

“Waylon was a great friend, one of the very best for 35 years, I’ll miss him immensely”

  • Johnny Cash


  1. Stop The World (And Let Me Get Off)
  2. Walk On Out Of My Mind
  3. The Chokin’ Kind
  4. Only Daddy That’ll Walk the Line
  5. Lovin’ Her Was (Easier Than Anything I’ve Ever Done)
  6. Sunday Morning Comin’ Down
  7. The Taker
  8. Honky Tonk Heroes
  9. Omaha
  10. You Asked Me To
  11. Black Rose
  12. We Had It all
  13. This Time
  14. I’m A Ramblin’ Man
  15. Amanda
  16. Oklahoma Sunshine
  17. Memories Of You And I
  18. Lonesome On’ry And Mean
  19. Are You Sure Hank Done It This Way
  20. Waymore’s Blues
  21. Bob Wills Is Still The King
  22. Suspicious Minds (w/ Jessi Colter)
  23. Good Hearted Woman (w / Willie Nelson)
  24. Mama Don’t let Your ladies Grow Up To Be Cowboys (w/ Willie Nelson)
  25. Luckenbach Texas (Back To The Basics Of Love)
  • Rico Ferrara, September 2021

2 thoughts on “Waylon Jennings – Nashville Rebel

  1. Waylon Jennings….wow! I got turned on to him , Merle Haggard etc listening to a Buffalo fm station in the early eighties. Decided then that country was ok. 👍

    Liked by 1 person

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