Waylon Jennings’ name is synonymous with “outlaw country.” That’s one Waylon Jennings story: about the Texas-born, hard-living country singer with a stubborn streak, who in the ‘70s broke with record-company convention to take creative control of his career, and who bonded with Willie Nelson and Kris Kristofferson and other independent-minded country-music rebels, together taking an outlaw stance of artistic nonconformity and determination. Nashville Rebel, the title of the new Jennings four-disc box set, came not from his breaking with Music City-rules in the ‘70s, but from the songwriter/cowboy role he played in the 1966 B-movie of the same name. But at the same time, the title works as the perfect descriptor of his career, because that how he’s remembered: as a county music rebel. Then again, by 1978 Waylon himself saw the “outlaw” notion as just another marketing tool, another method of categorizing to sell, as he expressed in his song “Don’t You Think This Outlaw Bit’s Done Got Out of Hand”. He still kept close with his outlaw pals, though, singing duets with Willie and releasing another Highwaymen album—with Nelson, Kristofferson, and Johnny Cash—in 1995, three years before his final studio album and seven years before his death.
The “outlaw country” thing was always as much about camaraderie as anything else. It was a reason to stick with his pals, to make music with those who understood. And that feeling of walking in the same footsteps as other like-minded musicians stretched back to the past, as all of these outlaws wore on their sleeves their debt to the giants of country music. In the mid-‘70s two Waylon Jennings singles, written by the man himself, made this point clear as day. First “Bob Wills Is Still the King”, a tribute that puts Wills on the highest pedestal (“it don’t matter who’s in Austin / Bob Wills is still the king”) while also declaring Waylon’s own love for the Texas tradition of honky-tonks and western music. And then its flip side, the lament “Are You Sure Hank Done It This Way”. As an anti-Nashville-showbiz statement it set up Jennings as an outlaw, but it’s also a statement of solidarity with the simple, from-the-gut approach of Hank Williams.
Jennings didn’t stick closely to the style of influences like Hank Williams and Bob Wills. Instead he modernized C&W music by pushing it further in the direction of rock; another chief element of the “outlaw” story is the way his music, more so than his peers even, got thicker in sound and more bluesy in style across the ‘70s, bridging the divide between rock and country in some ways. Of course, Jennings learned his style of playing guitar from his friend Buddy Holly, and carried that influence through his career. He played his guitar big and sharp, from the start. On a live album in 1974 (Waylon Live) he did a rip-roaring version of Jimmie Rodgers’ “‘T’ for Texas” that injected it with absolute fire. And by 1976 he was pulling out covers of the Marshall Tucker Band (“Can’t You See”) and Neil Young (“Are You Ready for the Country”, sounding more Rock and less Country than in Young’s version) and hitting the Country charts with them. But while his style of Country didn’t follow right in step behind Hank Williams, the spirit of his songs did.
A widescreen look at Jennings’ career, from start to finish, reveals that at every step of the journey his music retained that Hank Williams feeling of direct communication with down-on-their-luck listeners (“the common people,” as one 1967 song phrased it). That’s another Waylon Jennings story: his role in that tear-in-my-beer tradition, the way he’s spent so much of his career singing songs that seem designed to sound good to a listener drowning sorrows in drink. In that way he seems like a jukebox hero, like someone whose 40-plus-year career, all the way up to the decade preceding his death in 2002, left behind a legacy of jukebox classics: songs that compress into a few minutes a river’s worth of pain, within a melody you can sing to and lyrics you’ll remember. As a character in his 1970 hit “Singer of Sad Songs” expressed, “singer of sad songs / I need your services today.”
A listen straight through the career-spanning collection Nashville Rebel with fresh ears showcases that story even more so than the “outlaw” one. More specifically, it reveals the stream of songs Jennings sung about the ups and downs, or mostly the downs, of love. Within Nashville Rebel—and by relation within his overall discography, considering how comprehensive this set is—it’s easy to hear the Waylon Jennings songbook as a lengthy story of the struggles of love: heartbreak and lust, jealousy and joy, betrayal and confusion, and always hurt.
He wrote so few of the songs he sang—they were written by the greatest country-music songwriters, some singers and some not—but so many of them voiced similar concerns about life. The perspective is often that of the bad boy with heart, longing for love but not ready to give up his independence. Jennings’ stoic voice contains deep emotion just below the surface; that combination of headstrong stubbornness and deep-down sensitivity is a potent one when you have a voice like his.
One of his earliest Nashville singles was titled “My Baby Walks All Over Me.” It’s an admission that, when you’re in love, being bossed around isn’t always so bad. His first top 20 hit,” the Chet Atkins-produced “Stop the World (And Let Me Off)” took on love at the other end, not when you’re so giddy you’ll ignore problems but when the affair’s over and all you can do is express exhaustion at the rollercoaster nature of it (“I miss the wonder of your kiss / how could you leave me here like this”). Jennings’ string of singles from 1965 to 1968, included on the first disc in the chronological Nashville Rebel set, includes sentiments like these, together a veritable encyclopedia to the maze of love, tilting towards the madness of it:
“If to leave is a mistake / if I’m wrong in what I do / that’s the chance I’ll have to take”
“Don’t you shed a tear for me / I ain’t the love you thought I’d be”
“If the curtain should fall / I hope that it falls on you”
” How many hearts will break / how many will it take / to satisfy you”
“Your love scared me to death girl / it’s the choking kind”
“What we thought was our world / was only a dreamworld / and we just can’t go on like this”
These are bitter, pained songs, painting love as a war. There’s continual references to a lover trying to break Jennings down, to steal his mind, to ruin his life. And at the same time he sings of breaking hearts and regretting it, of wishing for a dream love that just couldn’t be. Elsewhere in these late ‘60s hits, there’s songs that take a somewhat more hopeful view of love, like the two-lovers-against-the-world story “I Got You”, a duet with Anita Carter, or the Harlan Howard-penned “Yours Love,” a touching wedding song, hinging on the promises of love. 1969 yielded the stunning back-and-forth “I Ain’t the One”, a duet with Jessi Colter, who that same year became his fourth wife. The R&B-inspired song takes his and her turns at laying out their rules for a relationship. And their statements are blunt, reflecting the tough love that exists in the song world of Waylon Jennings. Together they sing, “I ain’t the one who’ll go on loving you no matter what you do / I ain’t the one.”
Waylon Jennings and Jessi Colter performing “I Ain’t the One” on Hee Haw late ‘60s
In the early 1970s, Waylon Jennings’ music gets thicker with the blues, and even thicker with the fog of emotion. The sad songs get sadder, and the hopeful ones more hopeful. He asks a lover, using Willie’s words, to pretend he never happened, to erase him from her mind. He drives down the highway, lusting after the women he can never find, feeling “lonesome, on’ry and mean.” He stands in awe at the way things have turned out, singing “It’s not supposed to be that way / you’re supposed to know I love you.” He and Colter sing together about how spellbound they are, enough so that they’ll give love a chance even though it’s bound to fail: “I’ve got to take you back just one more time.” In 1974, to the gorgeous waltz of “Dreaming My Dreams With You”, Waylon quietly sings of the way his departed lover will always remain with him. She may have slipped out the door, but there’s no way he’s letting her slip from his mind.
Even in the thick of the “outlaw” period, when Jennings does an album of Billie Joe Shaver songs that would come to be seen as an outlaw-country classic (Honky Tonk Heroes), and a few years later when he Willie do albums and tours together constantly, these themes of love and its damage remain. Waylon and Willie co-write and sing a boisterous song about a “good-hearted woman in love with a good-timing man.” They jokingly warn mothers not to let their babies grow up to be wild, untrustworthy cowboys. Their biggest hit together, and Jennings’ highest-charting single of his career, is the immortal “Luckenbach, Texas (Back to the Basics of Love)”, a winning anthem written by Chips Moman and Bobby Eammons. It’s partly a lark about escaping from the claustrophobia of celebrity, though one made relevant to the singers by a mention of “Waylon and Willie and the boys.” But a dual storyline within it is Waylon’s singing to a lover about getting “back to the basics of love.”
Love can be simple, the song implies, though plenty of other Waylon Jennings songs are waiting in the wings to prove that notion wrong. Love, and escape, definitely feel simple when you’re listening to the song, with how easy its hook of a chorus goes down, and how quickly it becomes a singalong. That factor is what makes Waylon Jennings’ love-and-pain songs transcend the genre; his ease with a melody, and with his guitar, help him wrap these complicated feelings into a powerful and infectious few minutes, time and again. He’s sung songbook upon songbook of hum-able, addictive, sing-able songs that contain within them the ridiculous complexity of the human heart.
The final disc of Nashville Rebel, representing 1980—1995, kicks off with a 1980 Jessi Colter/Waylon Jennings duet that she wrote, which stands as another of the more optimistic takes on love within the set. “Storms Never Last” finds both husband and wife singing sweetly and gently to each other, about the triumphant feeling when everything’s going right, when the bad times have passed on by. It shows Jennings’ sensitive side—as does his stirring 1976 version of Jimmy Webb’s “MacArthur Park (Revisited)”, his 1984 cover of Dolly Parton’s slow dance “Waltz Me to Heaven”, his sublimely sad ballad “The Wurlitzer Prize (I Don’t Want to Get Over You)” (another tribute to the power of a sad song played over a jukebox), and so many other songs collected here. The toughness of his persona is part of what makes these moments so touching. An expression of absolute peace and acceptance, or even quiet resignation, can be an “outlaw” statement within a musical world filled with mistrust and sadness. Moments like those also round out the bigger picture by bringing to the surface the sensitivity lurking behind the demeanor of a country-western tough guy, the heart beating beneath the leather jacket. The truth is, though, even his most bitter songs of heartbreak express these feelings in their own way already—that’s what makes Waylon Jennings the jukebox king, the singer able to give voice to the rivers of tears flowing within the beers.
Waylon Jennings performing “Sick and Tired” at Willie Nelson’s 4th of July Picnic in 1974
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