Waylon: The Non-Outlaw Years

First things first- Waylon Jennings will always go down as an outlaw, and rightly so. ‘Ol Hoss is the definition of the outlaw country artist. He recorded what he wanted and how he wanted. He used his band. And, yes, he created a defining sound for the outlaw movement that went beyond just a sense of freedom in the studio- a defining sound with a driving back-beat that has become my personal favorite in the history of this storied genre we know as country music.

But it didn’t just happen overnight. Waylon was once a struggling artist like any other before he hit it big with his own sound. And before his death in 2002, he spent the last two decades or so recording music that wasn’t what fans had come to expect in the 1970s but was still nonetheless true to who Waylon was.

Waylon’s solo career began in 1961 with the first formation of his backing band “The Waylors;” he was active until his death in 2002. I would argue the defined beginning of Waylon’s outlaw days began with the release of The Taker/Tulsa in 1971, which included a batch of Kris Kristofferson songs. Waylon’s outlaw era would last, in my opinion, until the recording and release of his first sober album Never Could Toe the Mark in 1984. My timeline thus puts Waylon’s outlaw period at thirteen years. Thirteen years out of of forty year-plus career, meaning Waylon’s catalog is filled with material that deserves recognition and attention beyond the years in which he was one of the genre’s biggest stars.


The goal of this piece is to take a brief look at what Waylon was doing in the years before and after the outlaw era. It’s no secret that Waylon is my favorite artist of all-time, in any genre, and because of that, I feel it important to point out his contributions were not limited to the 1970s.

It should also be noted that by “outlaw” in this piece I’m referring to the widely accepted era in the 70s dominated by Waylon, Willie, and the boys. If we’re being honest, however, Waylon was an outlaw his entire career. Yet he’s mostly (and rightly) known for his outstanding artistry in the 1970s.


But a long time ago, Waylon was an artist with a dream and a goal stuck playing bars and clubs in Arizona. The bars helped Waylon find a signature element of his kind of music- blending rock (really rockabilly at the time) and country. Then Chet Atkins came calling thanks to tips from Skeeter Davis and Bobby Bare. Chet signed Waylon to RCA, and the first stage of his career was well underway.

Waylon’s first record Folk-Country was, according to Waylon in his autobiography, “Nashville’s scheme to snare some of the hootenanny folk audience, which was then starting to cross over to rock.” Yet Waylon makes it a point to say, “I didn’t mind the label…folk music was the original country music.”

Folk-Country contained many songs that would become standards for Waylon in the 70s like “Stop The World (And Let Me Off)” and “Look Into My Teardrops.” It was also a great example of the problems Waylon had with Nashville. Waylon wasn’t upset with the songs; they were quite good. It was *how* they sometimes sounded and *how* they were recorded. Waylon’s first records relied on studio musicians and a tight process. As Waylon recalls, “They didn’t understand the concept of a band…they actually got mad when I wanted to use the band on my recordings.”

Furthermore, Waylon “wanted to feel some excitement.” He said, “I could never play with a band that moves on the beat, or under the beat. I couldn’t get into it. It has to be on the edge…that’s the rock and roller in me.” He continued by writing, “Roy Acuff, Bill Monroe, Ernest Tubb…they had a style. You knew it was one of their records from the first intro…they didn’t sound like everybody else.”


Ironically, despite Waylon not entering his outlaw period yet, his first several records were still very much different from what the rest of Nashville was doing. Even with backing vocals and smoother production than what a typical Waylon song is known for, there was still a roughness and danger associated with his records- the prime example being his second record for RCA, Leavin’ Town.

Leavin’ Town was a pre-cursor to the pre-cursor of Waylon’s outlaw days. The guitars are twangy but not as emphasized. Steel guitar is scarce if barely heard at all. Shuffling drums. Yet the themes are Waylon as could be. Rambling, warning women not to love him because he’ll inevitably be on his way soon, a song or two with a tinge of regret.

One of the best songs on the album is “Doesn’t Anybody Know My Name.” It’s a downtrodden story from a military vet returning home from war. Everything’s changed, and no one in town knows who the narrator is. He can’t even find times at the train station so he can get out of the depressing scene. And then in the last verse, it’s revealed the man is blind. The song is filled with aching loneliness, and I’d put it up there with some of Waylon’s best work. In fact Leavin’ Town as a whole is one of his best ten records.


Another one of Waylon’s pre-outlaw records that’s worth talking about is Love of the Common People. The title track is a beautiful look at a family staying strong despite poverty and stark difficulties. After covering the Beatles’ “Norwegian Wood” on his previous album, Waylon once again returned with another cover, this time the Beatles’ “You’ve Got To Hide Your Love Away.”

Love of the Common People was another effort by Waylon to stand out given the parameters of what he could do in the studio. If he couldn’t use his band, if he couldn’t have more control over the production…he was going to at least record the songs he wanted.

Beatles’ songs, later the Stones’ “Honky Tonk Woman” on Singer of Sad Songs, “Brown Eyed Handsome Man” on Waylon. The signs were always there that Waylon was eventually going to wage an all-out assault on RCA Records for complete control of *his* music.


Waylon’s pre-outlaw vocals also warrant a mention. It’s not that his voice wildly changed. It just got rougher; as he gained more control over his work in the studio, he also stopped trying to croon. It’s a little known secret, but the heart of the country vocal is a croon. The difference between the pop croon at the time and the country croon was simply the accent. Take Willie Nelson for instance. His favorite singer? Frank Sinatra. There’s a long history of the croon in country music, particularly in countrypolitan material with artists like Jim Reeves and Marty Robbins.

Waylon’s croon was defined and smooth. And it worked. But for Waylon, as I mentioned earlier, simply making something work wasn’t good enough. He wanted to stand out. He wanted to be different. And his outlaw days were exactly the path he was going for.


Essential Waylon tracks (1966–1970):

“Stop The World (And Let Me Off)” -1966
“That’s the Chance I’ll Have to Take” -1966
“Leavin’ Town” -1966
“Time to Bum Again” -1966
“(That’s What You Get) For Lovin’ Me” -1966
“Doesn’t Anybody Know My Name” -1966
“Nashville Bum” -1967
“Norwegian Wood” -1967
“Everglades” -1967
“Foolin’ Around” -1967
“Love of the Common People” -1967
“Dream Baby” -1967
“The Chokin’ Kind” -1968
“Only Daddy That’ll Walk the Line” -1968
“Mental Revenge” -1968
“Just to Satisfy You” -1969
“MacArthur Park” -1969
“Brown-Eyed Handsome Man” -1970
“Honky Tonk Woman” -1970


Waylon’s legendary outlaw days came and went, and all of a sudden, new stars were everywhere. The outlaw era had made way for the Urban Cowboy movement to take over the genre before George Strait, Ricky Skaggs, Dwight Yoakam, and Steve Earle wrestled back control for traditionalist-minded artists. But Waylon was still around. He may not have been a huge star any longer, but he was about to record some of the richest and most poignant material of his storied career.


Everyone knows about Waylon’s participation with The Highwaymen, the greatest supergroup music has ever seen. But what was he doing with his solo career after the outlaw days were finished? The best answer may lie in many of the lyrics of his first album with MCA after he left RCA in 1985.

Will the Wolf Survive? was Waylon’s first record to be recorded digitally and the first since his pre-outlaw days on which his band didn’t play. Waylon certainly found himself struggling to adapt to the new recording process, saying, “I tried to keep an open mind about Jimmy’s (Bowen) way of doing things, and for his part, he let me try anything I wanted…the thing was, he knew I couldn’t do it right then.”

Waylon was happy with the songs, which included the title track (a cover of a Los Lobos’ record) and Steve Earle’s “The Devil’s Right Hand.” Also included was “Working Without A Net.” The latter song was fitting for Waylon now that he was sober. He had to record and preform without relying on drugs as he had for so many years. Waylon was frank about his struggles coming down from drugs, writing in his autobiography, “You lose all confidence when you come off drugs.” Yet despite the hard time he had adapting to a whole new part of his career, Will the Wolf Survive? contained plenty of material that lived up to Waylon’s high standards from a fan’s point of view. Will the wolf survive? If Waylon was the wolf, the world stood a pretty damn good chance.


Most of the albums Waylon recorded during the last decade or so of his career all contained songs fitting for an artist of Waylon’s stature. “Rose In Paradise,” off 1987’s Hangin’ Tough goes down as one of Waylon’s best songs he ever recorded. It’s a great story song and something a listener may not expect from Waylon. But Waylon was consciously trying to seek out new material and a new way of doing things. As I mentioned in the beginning of the piece, a key tenant of Waylon’s career was making sure he always tried to have his own identity, even if it made for a difficult process.

Waylon’s last record for MCA was Full Circle, released in 1988. Full Circle contains “Trouble Man,” a Waylon co-write with Tony Joe White. But one of the most beautiful songs on the album, and one of the best songs of Waylon’s career, is “Which Way Do I Go (Now That I’m Gone.” It’s quiet and solemn and deals with the uncertainty that comes when a man ends a relationship he knows isn’t meant to be. “Which Way Do I Go” is a stark difference from Waylon’s outlaw material in the 1970s which (mostly) dealt with no regret or uncertainty.

The Eagle also needs discussing. Released in 1990 during Waylon’s unsatisfying stay on Epic Records, The Eagle nonetheless found Waylon again recording songs fitting of his artistry. “Her Man,” later covered famously by Gary Allan, fit nicely within what Waylon was now singing about. And caring about. Jessi had been through everything with Waylon and now finally had her man settling down. “Where Corn Don’t Grow” is another song that warrants a mention. It’s a classic “the grass isn’t always greener” type of song, but it’s done in the Waylon-esque manner that isn’t preachy.

The rest of Waylon’s albums recorded up to his death in 2002 were mostly Waylon doing what he wanted. He knew he wasn’t going to get too many more hits, and he was content working with The Highwaymen and putting together his all-star band for the Never Say Die concert at the Ryman Auditorium. But I would be remiss without briefly talking about Waylon’s work with Old 97s. Waylon was sitting in on a performance of Old 97s in Atlanta and liked what they were doing. The band and Waylon hooked up and recorded some demos but was shelved after Waylon wasn’t a fan of the cover art which basically had each member of the Old 97s as an angel head floating around Waylon. Shooter Jennings approved the release in 2013 as Old 97s & Waylon, and listening to the record makes it so clear that the two were just meant to record together.

It’s such a shame Waylon’s health deteriorated. He had so much more to give, but there’s no doubt he spent the last two decades of his career recording material that he wanted, working with his best friends in The Highwaymen, and spending more time with his family. But besides, legends never die.


Essential Waylon tracks (1986–2000):

“Will the Wolf Survive?” -1986
“What You’ll Do When I’m Gone” -1986
“The Devil’s Right Hand” -1986
“Rose In Paradise” -1987
“Defying Gravity (The Executioner’s Song)” -1987
“Rough and Rowdy Days” -1987
“Trouble Man” -1988
“Which Way Do I Go (Now That I’m Gone)” -1988
“The Eagle” -1990
“Her Man” -1990
“Where Corn Don’t Grow” -1990
“Mansion On A Hill” -1992
“Waymore’s Blues (Part II) -1994
“Living Legends, Pt. II” -1996
“I’ve Always Been Crazy” (Live with Travis Tritt) -2000
“Iron Road” (with Old 97s) -recorded in 1996, released in 2013