Waylon Jennings’ long hair, bearded face, black hat and scowl marked him as the first man to bring real attitude to the country music genre. Born on June 15, 1937, by the time he took the stage in the 1960s, country might have had a few rogues already—such as Johnny Cash and Hank Williams—but Jennings made an institution out of his unapologetic swagger and his near menacing overtones of “Outlaw” country music. Indeed, Jennings cleared the way for the country megastars who followed him two decades later.
He formed his first band, The Texas Longhorns, at the age of 12 and dropped out of school at age of 14 to pursue a career as a radio DJ. At 17 he met up-and-comer Buddy Holly at the station and they became buddies. Holly produced Jennings first record “When Sin Stops (Love Begins)”.
Holly hired Jennings to play bass and took him on his1959 Winter Dance Party tour. While in Clear Lake, Iowa, Holly hired a small plane to fly them to the next gig. Waylon, whom Holly had invited to join him, gave up his seat to J.P. “The Big Bopper” Richardson who had the flu.
In the wee hours of February 3, 1959, the plane crashed shortly after takeoff. Everyone on the plane was killed: Holly, Richardson, Ritchie Valens and the pilot. Jennings was haunted for years after by a joking conversation he had with Holly before the fateful flight.
Jennings recalls: “Buddy says, ‘You’re not going on the plane tonight, huh?’ I said ‘No.’ He said ‘Well, I hope your bus freezes up.’ And I said ‘Well, I hope your plane crashes.’ I was awful young and it took me a long time to get over that.”
By 1965 Jennings had created a signature sound country-rockabilly style that included a bumping, “walk-all-over-you” bass, a “chicken-pickin’” guitar-playing technique and plain-spoken, rough-edged song lyrics. Jennings had also cultivated a rowdy image that made him almost as well-known as his songs. After their respective marriages went south, he even became Nashville roommates with Johnny Cash.
The two of them partied hardy on methamphetamines until Cash got sober and remarried. Jennings complained that Cash had “sold out to religion”. He later said: “Pills were the artificial energy on which Nashville ran around the clock.” Jennings was busted by the feds for “conspiracy and possession of cocaine with intent to distribute”.
(Jennings later sang about it in his song “Don’t You Think This Outlaw Bit’s Done Got Outta Hand?”) His offstage behavior rarely influenced his career and Jennings quickly became a much sought after headliner. Jennings put out nearly 70 studio albums. He also released dozens of hit singles including: “Walk On Out Of My Mind” and “Are You Sure Hank Done It This Way?”
Jennings also worked in motion pictures and on television. He was the narrator for the 1980s program The Dukes of Hazzard for which he also wrote and performed the show’s theme song. Unfortunately, country music got slicker in the 1980s and the majority of the genre’s legendary artists fell out of favor.
Jennings joined up with Willie Nelson, Kris Kristofferson and Cash to form The Highwaymen. They were a hit but Jennings remained an outlaw. He was a no show to his induction into the Country Music Hall of Fame.
He told the press: “It means absolutely nothing if you want to know the truth.” His addiction to cocaine intensified and he later estimated he spent $1,500 a day which left him bankrupt and owing over 2 million dollars.
He toured more in hopes of paying off the debt. Unfortunately, he lost his focus and the tours fell apart. He finally quit drugs altogether in 1984.
After quitting smoking in 1988 he had heart bypass surgery. His life-long battle with diabetes continued and in he was forced to stop most of the touring in 2000. By the end of the following year his left foot was amputated.
On February 13, 2002, at 64, Jennings died in his sleep in Chandler, Arizona due to diabetic complications. He was interred at the Mesa City Cemetery, in Mesa, Arizona. Those wishing to visit his grave must enter the cemetery and turn left on Ninth Street.
Stop by the sixth tree on the left. His grave is in the fourth row from the curb. He lies next to Gertrude Rice. Some say Jennings had escaped fate decades earlier only to fall victim to his own weaknesses in the end.
My name is Phoenix and . . . that’s the bottom line.