The Hard-Lived Truth: Waylon Jennings’ Tragic and Ramblin’ Life
Waylon Jennings, the legendary country music outlaw, often sang about heartbreak, hard luck, and tough choices – themes he knew intimately from a life marked by pain, struggle, and loss. His journey, from a fateful plane crash that haunted him to battles with addiction and financial ruin, paints a picture of a man who truly embodied the rugged narratives of his songs.
The Day the Music Died: A Haunting Premonition
In 1959, Waylon Jennings’ career was just beginning, with recording sessions produced by the superstar Buddy Holly. Holly invited Jennings to join him on tour alongside Ritchie Valens and J.P. Richardson, also known as The Big Bopper. On February 2nd, Holly chartered a plane to get himself and his band from Iowa to Fargo, North Dakota.
Jennings was originally scheduled to be on that flight, but Valens and Richardson were sick. In a twist of fate that would forever weigh on him, Jennings agreed to give up his seat to Richardson and take the bus instead. Holly jokingly told Jennings he hoped their bus broke down, to which Jennings chillingly replied, “I hope your ol’ plane crashes.” Horrifyingly, that’s exactly what happened. Shortly after takeoff, the plane crashed, killing everyone on board: Richardson, Holly, Valens, and pilot Roger Peterson. Jennings later confessed, “Never a week goes by when I don’t think of something about it and those guys.” This tragic event cast a long shadow over his life and career.
A Rocky Road to Love and Redemption
Jennings’ love life is most famously linked to Jessi Colter, whom he married in 1969. She is the mother of his well-known son, indie country star Waylon Albright Jennings, also known as Shooter Jennings. While his relationship with Jessi brought him stability, his early years were far from smooth, marked by three previous marriages and divorces.
His personal struggles took a significant toll. Jennings revealed to Rolling Stone, “When I met Jessi, I was pretty well at my lowest point. I weighed 138 pounds, and I was bent on self-destruction. Wallerin’ in self-pity was the biggest part of it, stayin’ depressed all the time and stoned. Jess was the best thing that ever happened to me.” Colter’s steadfast love was a crucial anchor in his turbulent life.
Battling Demons: Hepatitis, Cocaine, and Bankruptcy
Jennings’ hard-living lifestyle caught up with him in 1972 when, at 35, he became gravely ill after consuming a slice of pie and a glass of milk. He later recalled in his autobiography, Waylon: An Autobiography, that he had been warned not to eat local food during his tour due to a hepatitis outbreak. The warning came too late. Within days, he experienced severe back and kidney pain, and his wife noticed his skin had a yellow tint—a telltale sign of hepatitis. Though he initially resisted treatment, he eventually agreed to seek life-saving care at a nearby hospital after passing out.
The 1970s and 1980s saw Jennings gripped by a powerful cocaine addiction, a struggle that even led to a brief separation from Jessi Colter. Even an August 1977 police bust at a Nashville recording studio, where he faced charges of intent to distribute due to the sheer quantity of cocaine found, couldn’t stop him. The drug’s effects seemingly hadn’t impacted his music until a disastrous 1984 show in Portland, Oregon, where he mumbled through songs and stumbled off stage to a chorus of boos.
This low point spurred him to seek help. On Johnny Cash’s suggestion, he tried the Betty Ford Center. While not a complete cure, it inspired him to finally quit cold turkey, famously flushing $20,000 worth of cocaine down the toilet.
Despite earning substantial money as a prolific singer-songwriter and touring artist, Jennings often spent it as quickly as he made it. His autobiography reveals he went broke at least three times. At one point, his home and real estate were seized, bank accounts closed, and advances spent. He attributed this partly to a “$1,500 a day drug habit” and the expenses of a large staff including “a road manager, a band manager, a publicist, a secretary, a booking agent, a receptionist, gofers, and personal assistants all around.” In 1981, he filed for bankruptcy, citing a staggering $2.5 million in debt.
Lingering Health Battles and a Lasting Legacy
Even after quitting cocaine in 1984, Jennings endured significant heart troubles. In October 1988, he underwent a balloon angioplasty to clear a blocked artery. Just two months later, he experienced intense chest pains on his tour bus, leading to immediate triple-bypass surgery in Nashville. Fortunately, he never suffered a heart attack and made a full recovery. Under doctor’s orders, he canceled two months of shows and adopted healthier habits. He told UPI, “I had to change the way I eat. Smoking is what caused my problem. I smoked for 41 years, and I was smoking five and six packs a day in the last few years.”
His health struggles continued. While cocaine had suppressed his appetite, quitting the drug led to significant weight gain. Less than a decade after kicking his habit, Jennings was diagnosed with adult-onset, or Type II, diabetes, which led to severe complications. He developed vascular disease in both legs, and in 2001, a foot infection, compounded by his diabetes-ravaged body, necessitated amputation to save his life. Sadly, it was too late. Just two months later, the country legend passed away in his sleep at age 62.
Waylon Jennings’ life was a complex tapestry of triumph and tragedy. Despite the personal demons and hardships, his raw honesty, distinctive voice, and rebellious spirit solidified his place as a true pioneer of outlaw country music, leaving behind a profound and enduring legacy that continues to resonate with fans worldwide.