b. Wayland Arnold Jennings, 15 June 1937, Littlefield, Texas, USA, d. 13 February 2002, Arizona, USA. Jennings’ mother wanted to name him Tommy but his father, William Alvin, insisted that the family tradition of ‘W.A.’ should be maintained. His father played guitar in Texas dancehalls and Jennings’ childhood hero was Ernest Tubb, with whom he later recorded. When only 12 years old, he started as a radio disc jockey and then, in Lubbock, befriended an aspiring Buddy Holly. In 1958, Holly produced his debut single ‘Jole Blon’ and they co-wrote ‘You’re The One’, a Holly demo that surfaced after his death. Jennings played bass on Holly’s last tour, relinquishing his seat for that fatal plane journey to the Big Bopper. Jennings named his son, Buddy, after Holly and he recalled their friendship in his 1976 song ‘Old Friend’. Much later (1996) he contributed a poignant version of ‘Learning The Game’ with Mark Knopfler to the Buddy Holly tribute album notfadeaway.
After Holly’s death, Jennings returned to radio work in Lubbock, before moving to Phoenix and forming his own group, the Waylors. They began a two-year residency at a new Phoenix club, J.D’s, in 1964. The album of their stage repertoire has worn well, but less satisfying was Don’t Think Twice, Jennings’ album for A&M Records. ‘ Herb Alpert heard me as Al Martino, ’ says Waylon, ‘and I was wanting to sound like Hank Williams’. Bobby Bare heard the A&M album and recommended Jennings to record producer Chet Atkins.
Jennings started recording for RCA Records in 1965 and made the US country charts with his first release, ‘That’s The Chance I’ll Have To Take’. He co-wrote his 1966 country hit, ‘Anita, You’re Dreaming’, and developed a folk-country style with ‘For Lovin’ Me’. He and Johnny Cash shared two wild years in Nashville, so it was apt that he should star in Nashville Rebel, a dire, quickly made movie. Jennings continued to have country hits - ‘Love Of The Common People’, ‘Only Daddy That’ll Walk The Line’ and, with the Kimberlys, ‘MacArthur Park’. However, he was uncomfortable with session men, feeling that the arrangements were overblown. He did his best, even with the string-saturated ‘The Days Of Sand And Shovels’, which was along the lines of Bobby Goldsboro’s ‘Honey’.
When Jennings was ill with hepatitis, he considered leaving the business, but his drummer Richie Albright talked him into staying on. Jennings recorded some excellent Shel Silverstein songs for the soundtrack of Ned Kelly, which starred Mick Jagger, and the new Jennings fell into place with his 1971 album, Singer Of Sad Songs, which was sympathetically produced by Lee Hazlewood. Like the album sleeve, the music was darker and tougher, and the beat was more pronounced. Such singles as ‘The Taker’, ‘Ladies Love Outlaws’ and ‘Lonesome, On’ry And Mean’ showed a defiant, tough image. The cover of Honky Tonk Heroes showed the new Jennings and the company he was keeping. His handsome looks were overshadowed by dark clothes, a beard and long hair, which became more straggly and unkempt with each successive album. The new pared-down, bass-driven, no-frills-allowed sound continued on The Ramblin’ Man and on his best album, Dreaming My Dreams. The title track is marvellously romantic, and the album also included ‘Are You Sure Hank Done It This Way?’, ‘Bob Wills Is Still The King’, a tribute to his roots, and ‘Let’s All Help The Cowboys (Sing The Blues)’, an incisive look at outlaw country with great phased guitar.
The album, Wanted! The Outlaws, and its hit single, ‘Good Hearted Woman’, transformed both Willie Nelson and Jennings’ careers, making them huge media personalities in the USA (the 1996 Anniversary reissue added nine tracks, plus the brand new Steve Earle song ‘Nowhere Road’, sung by Nelson and Jennings). The first of the four ‘Waylon And Willie’ albums is the best, including the witty ‘Mammas, Don’t Let Your Babies Grow Up To Be Cowboys’ and ‘I Can Get Off On You’. In his autobiography, Nelson subsequently revealed a constant drug habit, while in his own audiobiography, A Man Called Hoss, Jennings admitted to 21 years addiction in an ode bidding farewell to drugs. The two artists will be remembered for shaking the Nashville establishment by assuming artistic control and heralding a new era of grittier and more honest songs. Whether they justified the tag ‘outlaws’ is a moot point - Jerry Lee Lewis was more rebellious than all the so-called Nashville outlaws put together.
Jennings was tired of his mean and macho image even before it caught on with the public. He topped the US country charts for six weeks and also made the US Top 30 with a world-weary song for a small township, ‘Luckenbach, Texas’, which is filled with disillusionment. Further sadness followed on ‘I’ve Always Been Crazy’ and ‘Don’t You Think This Outlaw Bit’s Done Got Out Of Hand?’. He aged quickly, acquiring a lined and lived-in face that, ironically, enhanced his image. His voice became gruffer but it was ideally suited to the stinging ‘I Ain’t Living Long Like This’ and ‘It’s Only Rock & Roll’. Jennings’ theme for The Dukes Of Hazzard made the US Top 30, but the outlaw deserved to be convicted for issuing such banal material as ‘The Teddy Bear Song’ and an embarrassing piece with Hank Williams Jnr. , ‘The Conversation’. The latter was included on Waylon And Company, which also featured duets with Emmylou Harris and actor James Garner.
Jennings often recorded with his wife, Jessi Colter, and he and Johnny Cash had a hit with ‘There Ain’t No Good Chain Gang’ and made an underrated album, Heroes. His albums with Nelson, Cash and Kris Kristofferson as the Highwaymen were also highly successful. Jennings and Cash had major heart surgery at the same time and recuperated in adjoining beds. A change to MCA and to producer Jimmy Bowen in 1985 improved the consistency of his work, including brilliant reworkings of Los Lobos’ ‘Will The Wolf Survive?’ and Gerry Rafferty’s ‘Baker Street’.
Despite his poor health, Jennings continued to look for challenges and Waymore’s Blues (Part II) was produced by Don Was. On the Red Hot And Country video, his thought-provoking ‘I Do Believe’ showed him at his best, questioning religious beliefs. Bear Family Records repackaged Jennings’ recordings in a 15-album series, The Waylon Jennings Files, which includes many previously unissued titles. In 1996 he signed to Justice Records and released the impressive Right For The Time, while Sting, Sheryl Crow and Mark Knopfler guested on 1998’s hard rocking Closing In On The Fire. In the same year, Jennings, along with other veteran artists Bare, Mel Tillis, and Jerry Reed formed the Old Dogs for a single recording session. The result produced a self-titled album released on Atlantic Records. Ill health hampered Jennings during the latter part of the decade, and in December 2001 his left foot was amputated because of an infection related to diabetes. He died two months later. Jennings had been inducted into the Country Music Hall Of Fame the previous year.
