For a man who often vowed that he “couldn’t go ‘pop’ with a mouthful of firecrackers,” Waylon Jennings became quite successful as a crossover artist, drawing young rock fans to his brand of country music, and exposing country fans to a style that drew from his early experience as bassist for, and protégé of, seminal rocker Buddy Holly. A much-admired singer, occasional songwriter and somewhat underrated guitarist, if he wasn’t country music’s original outlaw, Jennings became the point man of the “Outlaw” movement that gave country music a solid kick in the pants in the mid-’70s.
Jennings was born in Littlefield, Texas, on June 15, 1937. Before he was in high school, Jennings was working as a disc jockey, bandleader, and cotton-picker. He moved to the relatively bright lights of Lubbock in 1954, where he continued as a disc jockey and musician. He met Holly, who produced his first single (a version of the Cajun standard “Jole Blon” featuring New York rock legend King Curtis on tenor sax) and subsequently invited Waylon to join his post-Crickets band as bassist. Jennings was one of the seemingly thousands of musicians who later claimed to have given up their seat on the plane that crashed in Minnesota on February 3, 1959, killing Holly, “Big Bopper” J.P. Richardson, Ritchie Valens, and the pilot.
After two more years in Lubbock, Jennings moved to Phoenix, Arizona, where he became a local favorite and worked with many stars who passed through town. In 1963, Jennings recorded briefly for Herb Alpert and Jerry Moss’s A&M label in Hollywood, but it was songwriter-comic Don Bowman, who’d met him in Phoenix, who arranged for Waylon to meet RCA Victor’s Chet Atkins, who signed the singer to the label’s Nashville division.
For the next several years, Jennings accumulated a respectable list of singles, including country chart top 10 versions of Gordon Lightfoot’s “For Lovin’ Me;” “The Chokin’ Kind;” “Walk On Out of My Mind;” his signature “Only Daddy That Will Walk the Line;” and the less-played but Grammy-winning version of “MacArthur Park,” with vocal group The Kimberlys. He also roomed for a while with Johnny Cash, their association (though not their house-sharing and hell-raising) continued until Jennings’ death.
As his Nashville success continued, Jennings began collaborating with young writers from outside the Nashville establishment including Hoyt Axton, Alex Harvey, Kris Kristofferson, Shel Silverstein and Billy Joe Shaver. He also began writing with
fellow Texan and RCA artist Willie Nelson, though they wouldn’t record together until Nelson had left the label.
He also fought for, and won, the right to record with his own band – the usual Nashville practice in those days as now to use session musicians – and virtually produced his own sessions. The result was a string of even bigger hits, including “Pretend I Never Happened,” “You Can Have Her” (the old Roy Hamilton number), “This Time,” “I’m a Ramblin’ Man,” and tributes to pioneering country artists in “Are You Sure Hank Done It This Way” and “Bob Wills is Still the King.” He recorded the Marshall Tucker Band’s “Can’t You See” and Neil Young’s “Are you Ready for the Country” with notable success, and helped bring Willie Nelson to the younger audience that Jennings himself was reaching. First came “Good-Hearted Woman,” with Nelson’s voice and canned audience response dubbed onto a 1972 Jennings solo recording; the “new” 1975 version reached No. 1 on Billboard’s country chart and was voted Single of the Year by the Country Music Association.
The 1976 Wanted: The Outlaws album was released by RCA, issued under Jennings’ name but including vintage tracks by his wife, Jessi Colter; singer/songwriter Tompall Glaser; Willie Nelson; and the “Good-Hearted Woman” duet. The album became a million-seller and went a long way toward launching Nelson’s breakthrough.
The hits continued for Jennings, paralleled by an increasing cocaine dependency, which he eventually overcame. After his contract expired with RCA, he recorded for labels including MCA, Epic and Justice, with varying degrees of artistic and commercial success. He never regained the ground he’d lost, though, and died at his Arizona home in February 2002. He had, though, lived to see his election to the Country Music Hall of Fame.
These days, his son, Shooter Jennings, continues the family music tradition, enjoying a successful career himself.