Waylon Jennings - Biography
By Charles Reece
Waylon Jennings was country music’s Martin Luther, bringing about the Outlaw Reformation that would forever change the way Nashville powers-that-be treated their artists. Before Waylon, the genre was largely under the mediating control of producers. They chose the songs, the studio musicians and the arrangements for the artists. After Waylon, the artist could do all of these things (at least, the possibility now existed). Of course, none of this would have amounted to a hill of beans had he not done something aesthetically worthwhile after wresting control of the means of production. In a capitalist system where popularity has become the measure of art’s value and art is too often manufactured to achieve this goal, it is a rare strain that communicates with the sublime through the language of the vox populi. Bob Dylan achieved it, as did Miles Davis and Frank Sinatra; these are Jennings’ peers.
The first of four brothers, Wayland Arnold Jennings was born on June 15, 1937, in Littlefield, a small town located in the prime cotton-picking region just South of the Texas panhandle. His parents, William Arnold (who went by his middle name) and Lorene Beatrice (née Shipley), were field laborers, an economic class not quite as high as the sharecropper. Following the Jennings’ tradition of naming the eldest with the initials WA, Arnold and Beatrice christened their firstborn ‘Wayland,’ but changed the spelling to ‘Waylon’ after a minister mistakenly thought he was named after a Baptist college – the family belonged to the Church of Christ, which had a different take on faith. Beatrice, however, never got around to changing the name on the birth certificate. Waylon never had much use for religion, believing a man is good because of his actions, not his beliefs about where he is going after death.
Arnold was an amateur musician who taught Beatrice to play guitar. The parents raised their boys with a love for country music, particularly that of Bill Monroe and Ernest Tubb. Along with Waylon, his brothers Tommy, James and Philip (“Bo”) all grew up listening to the Grand Ole Opry on the radio. Waylon, in particular, was fond of Tubb, imitating the singer with a broomstick guitar until his mother bought him a real one for five bucks. With a few lessons from Beatrice, he was playing it by age eight.
Child labor laws not being much more than theoretical back in those days, Waylon was working even before he was playing a guitar. He picked the cotton fields until Albert managed to buy a dairy and produce store in Littlefield. By the age of sixteen, Waylon had reached his limit with physical labor and school, dropping out during the tenth grade to pursue a career in music. Although he had already demonstrated a knack for performing live when he won a talent show singing Carl Smith’s “Hey Joe!,” his first job in music was as a disc jockey for Littlefield’s local radio station KVOW in 1954. Along with early adulthood came his first wife, Maxine Lawrence, whom he married at the end of 1955.
As a disc jockey, Jennings developed an eclectic taste in American music. In addition to his early inspirations Hank Williams and Hank Snow, he became enamored with Elvis Presley and rock and roll, as well as its predecessors in the regional black music. In fact, it was his insistence on playing R&B at KVOW that led to his termination after the owner had repeatedly forbade him from doing so. Jennings landed another DJ gig in 1957 at the Lubbock station KLLL, where his manic on-air persona and varicolored taste garnered him a following among teenagers. It was at KLLL where Jennings became fast friends with Buddy Holly, who had just returned home from supporting his string of hits on tour.
Only one year his senior, Holly became a mentor to Jennings, teaching him about the music industry along with selecting and producing his first single, the Cajun song “Joe Blon” (for which Jennings made up the lyrics that he could not learn phonetically). After Holly broke from his supporting band, The Crickets, he asked Jennings to play electric bass for his 1959 tour with, among others, Richie Valens and J. P. “The Big Bopper” Richardson. Jennings became part of rock mythos when he gave up his seat on Holly’s charter flight to the ailing Big Bopper on February 3, 1959. Before departure, Holly teased Jennings about having to ride on the drafty tour bus. Jennings jokingly responded with a hope that the plane crashed. After the plane did crash, taking Holly’s life, it took him years to get over the grief resulting from what had originally seemed like meaningless banter.
“Joe Blon” was released on the Lubbock-based label Brunswick Records a month after the accident, but failed to be noticed even regionally. Jennings returned to disc jockeying in Lubbock and surrounding areas for a brief period while mourning the loss of his friend, but soon moved with his family to Coolidge, Arizona, for a job at the local station KCKY. Shortly before leaving Lubbock, he recorded four songs for local label Trend ’61 Records, including the single “My Baby Walks All Over You” (1961) with it’s B-side, “The Stage,” a tribute to his late friend. He was unhappy with the way the producer attempted to make him sound like a teenager by slightly speeding up his vocals.
He was not the most faithful of husbands, nor did his pursuit of a music career leave much time for his family. Jennings’ first couple of years in Arizona proved to be fairly miserable on the home front. Maxine hated Coolidge and hated her husband’s ambulant lifestyle even more. He was falling for Lynne Mitchell, who had decided to leave her husband and follow the singer to Coolidge after meeting him in Salt Lake City, Utah. Maxine moved back to Texas with their four children (Terry, Julie Rae, Buddy and Deanna), and Lynne became the second Mrs. Jennings.
Jennings had been developing a following by playing clubs in the region, but it was upon his relocation to Phoenix that his career really took off. It was there that he formed the earliest version of his backing band, The Waylors. In 1963, Lynne gave birth to Tomi Lynne, Jennings’ fifth child. That same year, he received his first recording contract, with Herb Alpert and Jerry Moss’ newly formed A&M Records in Hollywood, California. Don Bowman, an old disc jokey friend from KLLL, was visiting on his way to Hollywood. Impressed by what his pal was doing, Bowman passed along some recordings to Alpert.
Waylon Jennings and The Waylors started off as a three-piece in the style of Johnny Cash and the Tennessee Two (two guitars, with one keeping the rhythm, and a bass), but expanded in late-1964 to include drummer Richie Albright, a man who would remain a close friend and collaborator throughout Jennings’ life. Their set-list demonstrated the same eclecticism that Jennings had shown as a disc jockey, combining hard country favorites with current rock and roll hits, R&B and Greenwich Village folk. By the middle of the year, they had set up residency at Jim Musil’s nightclub, JD’s, located near Arizona State University. Jennings had helped Musil in setting up the sound system for the club, and in return Musil released the singer’s first long-player, Waylon Jennings at JD’s (1964 Bat Records). Despite the name, it is a studio recording, featuring Jennings’ versions of songs ranging from George Jones’ hit “White Lightning” to Bob Dylan’s “Don’t Think Twice.” Available only at the club, a second pressing immediately followed after the first sold out. As was evident from his fan-base at JD’s, Jennings always appealed as much to college students as he did to the rednecks.
While touring through Phoenix, Bobby Bare bought a copy of Jennings’ first A&M single, “Just To Satisfy You” (1964), and was so bowled over that he took it back to Chet Atkins at RCA in Nashville, Tennessee, encouraging the producer to sign the singer posthaste. As it turned out, Bare was not the only RCA artist singing Jennings’ praises, both Skeeter Davis and Duane Eddy were promoting him to Atkins, as well. The single, co-written with Bowman, was Jennings’ first bona fide classic and a good representation of the folk-country fence he was straddling back then. He would re-record the song many times (most memorably in honky-tonk form on Waylon Live in 1976 and as a #1 hit duet with Willie Nelson in 1983), but it was Bare’s version (in 1965) that became his first composition to enter the Top 40.
When Atkins asked Jennings to join RCA’s roster, he was ready to go. Alpert never understood his music, seeing the handsomely lanky singer with a lacquered pompadour more as a potential teen idol than hard country singer. With Albert’s own musical career taking off with The Tijuana Brass, he had no desire to stand in Jennings’ way, so let him out of his contract. His second marriage was destructing just as the first had. He was having an affair with a leggy blonde from a wealthy family by the name of Barbara Rood, which made him feel both guilty and straightjacketed (as expressed in his song “Anita, You’re Dreaming”). Thus, in 1966, after some of his earliest recordings for RCA made their way into the Country Top 20 (“Stop The World (And Let Me Off)” at #16 and the aforementioned “Anita” at #17), he left Arizona for Tennessee, finding there a like-minded roommate and his musical paragon, Johnny Cash, who himself was currently in-between spouses, living in Madison (bordering Nashville). With a friendship that endured until Cash’s death, they were in many ways mirror images of each other: baritone delivery, black-dominated attire, a style rooted in the macho posturing of old Westerns and a longtime dependence on amphetamines. Jennings took his first pill a couple years prior, and it would take him till the mid-1980s to kick the habit.
Atkins, along with his aesthetic cohort Owen Bradley at Decca Records, had revolutionized country music by putting the producer in control, using a group of session musicians that they trusted – the “A-Team” – to create radio-friendly arrangements for what came to be called the Nashville Sound, or countrypolitan. If a fiddle was included, it tended to be part of lush string background, and the steel guitar was replaced by pop-oriented background singers (most notably led by Anita Kerr). The phenomenal success artists like Patsy Cline and Don Gibson had with this mode of production might have blinded Atkins to other possibilities, but he was always a fervent believer in country music and the artists working under him. For his part, Jennings was an admirer of what Atkins had accomplished and expressed just as much respect for the studio musicians under his employ. Contrary to the standard countrypolitan procedure, Atkins invited the Waylors to record with the session musicians. Jennings was still searching for his sound, and this compromise made for a string of good and moderately successful records that accurately reflected his eclectic interests at the time: Folk Country (1966 RCA, #9 on the Country Album chart), Leaving Town (1966 RCA, #3) and Nashville Rebel (1966 RCA, #4). It was during this period that Jennings had his first Top 10 single, with a rocking version of Gordon Lightfoot’s “(That’s What You Get) For Lovin’ Me,” peaking at #9 in 1966.
Nashville Rebel is the soundtrack Jennings made for the movie of the same name in which he starred. He portentously played the part of Arlen, a young country singer entering Music Row who insists on doing things his way, earning the animosity of the establishment in return. Premier country songwriter Harlan Howard wrote the two most significant songs for the film, the title track and the single “Green River” (peaking at #9 in late 1966 and featuring Jennings’ imitation of Roy Orbison). Coincidentally, it was when working on another of Howard’s songs that a fracture began to develop between Jennings and the RCA house style.
Jennings was first and foremost an interpreter of songs. When he wanted to record a song, it was because it enunciated who he was – even if (like most of his recordings) it was written by someone else. When his versions worked, as they so often did, they claimed a sense of propriety over the songs themselves. Thus, when Howard and Atkins’ star picker Jerry Reed began to sweeten the arrangement on the former’s “The Chokin’ Kind” that Jennings and the Waylors had recorded for his next album, Waylon Sings Ol’ Harlan (1967 RCA, #4 on the Country Albums chart), he stormed out of the studio. Jennings felt particularly close to the song as it encapsulated his current relationship with Rood, who did not appreciate his rambling approach to life any more than his former wives had. It was as if his song was being taken away from him. The speed intake did not help Jennings’ stress level, but coolheaded Atkins (who had previous experience dealing with drugged-up musicians) stepped in and calmed everyone down. The song was re-recorded, but continued to suffer from a maudlin backing chorus. Regardless, it was Jennings highest-ranking single to date, peaking at #8 in 1967, and his first hit to be credited to the Waylors. Rood became his third wife that same year only to be his third and final ex-wife the following year.
The end of the 1960s was a difficult period for Jennings, personally if not commercially. In addition to the failure of his third marriage, his father died in 1968; a tour bus crash took the life of his bassist, Walter Conway; his close compadre and only remaining early Waylor, Albright, left in 1969 due to stress following an arrest for marijuana possession; and, most importantly, Atkins became a vice president of RCA, increasingly leaving production duties to Danny Davis. Jennings remained proud of the records he made during this time, but felt that they were often too much like all the other hits coming off the Nashville conveyor belt, namely good solid product. He would record a song one way, only to return to find so much by-the-book tinkering had been applied that he no longer recognized himself in the song. Davis’ métier was as a horn arranger, who had a proven countrypolitan track record with The Nashville Brass. The Nashville Sound was the right method for him and he lacked the management skills of Atkins. Unfortunately for Davis, he entered the picture just as Jennings was beginning to reevaluate his musical direction. As Atkins later admitted, putting those two together in the studio was the worst mistake he made with the latter’s career.
Jennings’ records for RCA in the 1960s continued to sell well, all of them entering the Country Album Top 20, with half of them making the Top 10: Love of the Common People (1967, #3), Hangin’ On (1968, #9), Jewels (1968, #6) and Just to Satisfy You (1969, #7). Likewise, his singles regularly placed in the Country Top 10, most notable of which being the Jimmy Bryant-penned “Only Daddy That’ll Walk The Line” – a patriarchal classic every bit the equal to The Rolling Stones’ “Under My Thumb.” The single spent five weeks at #2 in 1968 and was his most successful recording of the decade, becoming a permanent part of his repertoire. In 1969, Jennings’ desire to experiment with a wider range of material dovetailed with Davis’ ability as an arranger on “MacArthur Park,” a piece of existential melodrama that had been a hit for the actor Richard Harris. Jennings’ version was the single for the album Country Folk (1969 RCA) that he recorded with the vocal group The Kimberlys, a pair of brothers married to a pair of sisters. The single peaked at #23 and won him his first Grammy (for performance by a vocal group). The album was the first of his to show up on the Top 200 Pop chart at #169 and made it to #13 on the Country chart.
A day after Albright quit, Jennings’ love life took a turn for the better in October, when he married Mirriam Eddy, who was recently divorced from his old Phoenix pal, Duane Eddy. As a musician herself, taking the name Jessi Colter upon signing to RCA that year, she never made Jennings choose between a musician’s life and domesticity. They remained married for the rest of Jennings’ life and had a fruitful musical career together, the beginning of which was Colter’s debut album, A Country Star Is Born (1970) that Jennings’ co-produced. They followed the record with two Top 40 duets: covers of the Elvis Presley hit “Suspicious Minds” in 1970 and Buck Owens’ “Under Your Spell Again” in 1971. The couple would eventually release an entire album of duets in 1982, titled Leather and Lace (RCA, #11 Country, #43 Top 200), with their rendition of Colter’s doleful masterpiece, “Storms Never Last” (#17).
The partnership with Davis finally combusted in 1970 when Jennings, with a .22 Magnum at hand, told him to go sit in his booth and keep quiet. The event occurred during the period in which Jennings had been traveling back and forth to Hollywood to record Singer of Sad Songs (1970 RCA) with producer-singer-songwriter Lee Hazelwood. Recording with relatively few musicians, Hazelwood’s unadorned production style pointed the way to the Outlaw decade on the horizon. Despite being recorded in RCA studios, the suits back in Nashville did not appreciate Jennings’ use of an outsider producer on an out-of-town album, and refused to promote it. Regardless, the album made it to #23 on the country chart. Over the next couple of years, Jennings increasingly associated with a group of singer-songwriters, who sailed under the Nashville radar, including Mickey Newbury, Kris Kristofferson, Shel Silverstein and Billy Joe Shaver. With their literary sensibility and oblique approach to the country genre, Jennings was beginning to get a sense of what artistic freedom was like.
Jennings and Kristofferson teamed up to sing a bunch of Silverstein’s songs for the soundtrack to Ned Kelly (1970 United Artist), a film about the infamous Australian outlaw starring Mick Jagger in the title role. Jennings’ next album, The Taker/Tulsa (1971 RCA, #12 Country, #96 Top 200), featured his versions of Kristofferson’s classics (e.g., “Loving Her Was Easier” and “The Taker”). The title track (1970, #5 Country single) was from his sessions with Davis, but the majority of cuts were produced by Ronnie Light. Light was a much more accommodating producer than Davis, granting Jennings a good deal of leeway for the next two years that they worked together. However, as Jennings readily admitted, he put Light through the wringer, having had enough of compromising. The songs were what now many call progressive country, but the sound, with an increasing prominence of the steel guitar, signaled a return of hard country honky tonk.
La politique des Outlaw came about by Jennings’ close associations with four people: Willie Nelson, Richie Albright, Tompall Glaser and Neil Reshen. Fellow RCA-artist Nelson was having similar problems to Jennings’ with the Nashville power structure by the time they were working together on the latter’s Good Hearted Woman (1972, #7 Country). Nelson’s solution was to retire to Austin, Texas, until he signed a much better deal with Atlantic Records. Jennings was ready to leave, too, despite the success of the album’s two singles, the best remembered being his and Nelson’s title track (#3 Country single). Nelson began reporting back from Austin about the burgeoning country-rock congregation, where the long-hairs were as big a fanbase of classic country as the rednecks. Jennings realized that the main problem with the Nashville Sound was not the producers, but that it broadened country’s audience by making the music poppier, rather than expanding the taste of potential new listeners.
As he lay recuperating from hepatitis that he had contracted while touring the Navajo reservations in Phoenix during an epidemic, Albright returned to the Waylors from touring with the rock band Goose Creek Symphony. He informed Jennings of the way rock music contracts were set up and how the bands toured with their own sound systems. He also introduced the singer to Goose Creek’s New York-based lawyer, Reshen, who became his manager. Jennings’ contract was up, and Atlantic was courting him, so he reminded the RCA representatives that they had already lost Nelson. By the time negotiations were done with Jennings’ fast-talking, carpetbagging Yankee lawyer, he had complete control over production, album designs, studio musicians, song selection and was to receive a higher percentage of sales than even Atkins received. Reshen had set a precedent that continues to influence contract negotiations in Nashville to this day. He became Nelson’s manager a month later.
The bearded image began while Jennings was convalescing. Reshen encouraged him to keep it as it made him more contemporary looking, particularly with the longer hair he was now sporting. The term ‘outlaw’ first became associated with him on the Lee Clayton-penned title track to Ladies Love Outlaws (1972 RCA), an album released against Jennings’ wishes (since he had not finished dubbing his vocal tracks due to his illness). His first truly outlaw album – the first one under his new contract – was Lonesome, On’ry and Mean (1973 RCA). It contains some songs recorded during the sessions with Light, such as its two Top 10 singles, Nelson’s “Pretend I Never Happened” (#6) and Bill Cook’s “You Can Have Her” (#7). Most significantly, the album has songs from sessions with Jennings as sole producer, featuring the Waylors, such as his versions of Newbury’s “San Francisco Mabel Joy” and Danny O’Keefe’s “Good Time Charlie’s Got The Blues.” Any fears the RCA executives had about turning him loose proved to be unfounded, since the album reached #8 on the Country chart.
Jennings’ revolution was completed by his production relationship with old pal Tompall Glaser. Together they produced Honky Tonk Heroes (1973 RCA, #14 Country, #185 Top 200), Jennings’ album of – with one exception – songs either written or co-written by Billy Joe Shaver (including the #8 single, “You Asked Me To,” which they wrote together). It was the first album where Jennings’ interest in sequencing the songs to make a holistic work was fully realized. It did not sell quite as well as his previous one, but is now generally recognized (at least, among his devotees) as the first of his truly legendary works.
Although Glaser did not produce any of This Time (1974 RCA, #4 Country), it was at his Glaser Sound Studio, nicknamed “Hillbilly Central,” where Jennings, with the help of Nelson, recorded the album. (Jennings would record his next couple of albums there.) It was RCA policy for their artists to use only company-owned studios with their unionized engineers. By ignoring this policy and busting the union, Jennings made what was essentially an independent album that led to the downfall of the label-owned studios and the flourishing of the independent studio system that currently persists in Nashville. Jennings’ reward was the title track becoming his first #1 hit single (a song that he wrote).
Demonstrating that Jennings had no particular animosity towards studio musicians, he used them (along with the Waylors) for The Ramblin’ Man (1974 RCA, #3 Country, #104 Top 200), which Glaser and Ray Pennington helped produce. The most commercially polished album of his outlaw period, it contains two #1 singles that have become some of Jennings’ most readily identifiable songs, the Pennington-written “I’m A Ramblin’ Man” and Bob McDill’s “Amanda” (which would not reach #1 until 1979, as the single for the Greatest Hits collection). However, it is with Jennings’ subsequent release that – according to him, the critics and his fans – he made his definitive statement in the studio.
Featuring three Top 10 hits (Jennings’ own “Are You Sure Hank Done It This Way” and “Bob Wills Is Still The King, both at #1, as well as his take on Allen Reynolds’ “Dreaming My Dreams With You” at #10), Dreaming My Dreams (1975 RCA) became the first in a string of six #1 albums during the 1970s (only interrupted by the soundtrack he and Nelson released for Mackintosh and T.J. in 1976). The album was co-produced by Cowboy Jack Clements (famed producer of Cash and Jerry Lee Lewis for Sun Records and who was now married to Colter’s sister, Sharon). What became the signature sound for Jennings and the Waylors was perfected here: in particular, Duke Goff’s thick, resonant bass backing Ralph Mooney’s equally sonorous honky-tonk steel guitar playing. The only other record possibly more constitutive of this period is his double-longplayer Waylon Live (1976 RCA, #1 Country, #46 Top 200). Recorded live in 1974 over two nights in Texas (Dallas and Austin), the album features looser, more extemporaneous versions of Jennings’ classics, including outlaw versions of some from his 1960s’ oeuvre.
The movement (such as it was) received its name around the release of This Time when Hazel Smith, the publicist for Hillbilly Central, described as “outlaws” the ragtag bunch hanging out there (including Kinky Friedman, Donnie Fritts, Guy Clark, DJ Captain Midnight and Ron “Dr. Hook” Sawyer). As a brandname, it proved to be pure marketing brilliance, helping to sell Jennings and cohorts to a rock audience fancying itself and its music as rebellious. In order to capitalize on the success these artists were having with the outlaw imagery, RCA released Wanted: The Outlaws in 1976, a collection of previously released material from Jennings, Nelson, Colter and Glaser. Wanted became the first country album to sell a million copies, reaching #1 on the country chart and #10 on the Top 200, receiving the Country Music Award (CMA) for Best Album. Jennings and Nelson’s new recording of “Good Hearted Woman” stayed at #1 for four weeks and won CMAs for Best Single and Best Duo Performance. Ever the honorable gentleman, Atkins admitted that he had been wrong to take Jennings’ artistic ambition as mere destructive rebellion. As the propaganda wing of the Nashville establishment, the Country Music Association was hardly on good terms with Jennings; they simply had to accept his way of doing things due to his success. His contempt for the CMAs was made widely known the previous year when he won Best Male Vocalist, calling the award a “goddamn bowling trophy.” He asked for his name to be removed from consideration this time around, but the Association refused. Thus, he was not pleased when the less ideological Nelson showed up for the ceremony, amidst jokes and allusions about how Jennings did not properly respect country music.
His popularity only increased over the next couple of years with the releases Ol’ Waylon (1977 RCA, #1 Country for 13 weeks, #15 Top 200) and Waylon & Willie (1978 RCA, #1 Country, #12 Top 200). The former was Jennings’ first platinum selling album largely due to the strength of the single, Bobby Emmons and Chips Moman’s “Luckenbach, Texas (Back To The Basics Of Love).” The song was based on Glaser’s recent business dispute with Jennings that forever severed their friendship. Jennings had never been to Luckenbach and hated the song, but recognized a hit when he heard one. It stayed at #1 for seven weeks, and he was stuck with it. In addition to his role as the announcer for the television series The Dukes of Hazard and his theme for the show (“Good Ol’ Boys” – #1 in 1980), it was “Luckenbach” that earned him a place in the pop pantheon. More than any other, the song established a cowboy mythology around the Willie-Waylon relation that made it nigh impossible to think of one without the other. Waylon & Willie was the first and most successful of his four duet records with Nelson (the other three being 1982’s WWII on RCA, 1983’s Take It To The Limit on CBS Records – both peaking at #3 – and 1991’s Clean Shirt on Epic Records, peaking at #28). The album went platinum and contains four #1 singles: Jennings’ two solo numbers, “The Wurlitzer Prize” and “Lookin’ For A Feeling,” plus the duets “I Can Get Off On You” and “Mammas Don’t Let Your Babies Grow Up To Be Cowboys” (the last of which earned Nelson and him a Grammy for Vocal Duo).
Along with Jennings’ rock and roll-sized touring equipment came a similarly excessive lifestyle (earning him the nickname that became the titular subject of his bluesy free-associative “Waymore’s Blues” on Dreaming My Dreams). Infidelity remained a constant temptation on the road and he had developed a $1,500 a day cocaine habit by the mid-1970s. In 1977, during the recording of Hank Williams, Jr.’s The New South (Warner), which Jennings co-produced with Albright, DEA agents burst into the studio with a search warrant for a courier package they knew contained cocaine (as it had been investigated before its arrival). Jennings’ secretary had brought it over from his office earlier that morning. He would have been facing up to fifteen years in prison had the agents been able to locate it, but their search warrant was for his office, not the studio. While they were awaiting a new warrant, Albright managed to flush the cocaine down the toilet. Jennings was arrested due to some residual traces of the drug found, eventually spending over a $100,000 in legal fees to get the charges dismissed. He turned the experience into what became the denouement of his outlaw years: “I’ve Always Been Crazy” (#1 for four weeks) and “Don’t You Think This Outlaw Bit’s Done Got Out Of Hand” (#5) for the final album in his streak of #1s, I’ve Always Been Crazy (1978-RCA, #48 on Top 200). Jennings had managed to conquer every obstacle placed before him, including the law.
He closed out the decade with two #1 singles (Chuck Howard’s “Come With Me” and Rodney Crowell’s “I Ain’t Living Long Like This”) from What Goes Around Comes Around (1979 RCA), an album that stayed at #2 for fourteen weeks, kept from the top slot by Kenny Rogers’ Kenny. Rogers’ overwhelming success paved the way for the bland pop-with-a-twang New Country that began to dominate the radio in the 1980s, by which time Jennings had pretty much said what he had to say musically. What surely did not help his creative drive was a couple of personal crises that began the decade, a financial debt of $2 million resulting from poor business management and his equally crippling drug addiction. With good ol’ boy determination, he paid off the debt through relentless touring and quit cocaine cold turkey by sequestering himself and his family (Colter and their young son, Waylon “Shooter” Arnold, Jr.) to the Phoenix desert.
Similar to Sinatra’s Reprise period, the music during Jennings’ autumnal years played more to his established image (signified by the winged W logo), rather than the other way around. Nevertheless, he still had a few #1 albums left in him. First, Music Man (1980 RCA) largely owed its success to the inclusion of “Good Ol’ Boys” and “Storms Never Last.” Second, The Highwaymen (1985 CBS) was a country supergroup teaming Jennings with his fellow aging Nashville renegades: Cash, Nelson and Kristofferson. The album’s title and the band’s de facto name came from Jimmy Webb’s song, with which they had a #1 hit (awarded the Grammy for Best Song in 1986). They released two more albums together (Highwaymen 2 in 1990, MCA, The Road Goes on Forever in 1992, Liberty – neither doing as well as the first) and starred in the 1986 TV remake of John Ford’s classic film, Stagecoach, in which they played actual outlaws of the Old West. Finally, Will the Wolf Survive (1986) was Jennings’ first album for MCA Records after leaving RCA due to declining sales. He was with MCA for the remainder of the decade, and it was while there that he had his final #1 single, Steward Harris and Jim McBride’s “Rose In Paradise” from 1987’s Hangin’ Tough.
Jennings released a few albums with Epic Records in the early 1990s (including The Eagle, his last to chart in the Top 10) before switching to independent labels, including his own WJ Records. His body was failing him by this time; too much hard living had finally taken its toll. He had to have bypass surgery in 1988 due to chest pains. After giving up cocaine, he often became ravenous, resulting in weight-gain, which exacerbated diabetes. Poor circulation resulted in a minor stroke in the 1990s, which required him to use a wheelchair on tour. Years of heavy smoking led to emphysema and years of playing guitar caused carpal tunnel syndrome, both of which decreased his ability to play live. His last studio album, Old Dogs (1998 Atlantic), was with another supergroup, consisting of friends from his earliest days in country music – Bobby Bare, Jerry Reed and Mel Tillis – singing the songs of Shel Silverstein. He left Nashville for good in 2000, moving to Chandler, Arizona, with Colter and Shooter. The Country Music Association finally got over its longstanding grudge, inducting him into The Country Music Hall of Fame in 2001 (with his son, Buddy, accepting on his behalf). Two months later, his left foot was amputated. He resolved to continue touring, but never got the chance. On February 13, 2002, he died in his sleep at home.