Waylon Jennings sang about heartbreak, hard luck, and hard choices.
And as it turns out, he knew all about that stuff, as he lived a tough life marked with
pain, struggle, and loss.
Here's a look at the tragic, ramblin' life of Waylon Jennings.
Waylon Jennings was just getting his career started in 1959 with some recording sessions
produced by superstar Buddy Holly, who invited Jennings to come on a tour alongside fellow
musicians Ritchie Valens and J.P. Richardson, aka the Big Bopper.
On the 2nd of February, Holly chartered a plane to get himself and his band from Iowa
to Fargo, North Dakota.
Jennings was supposed to be on the flight, but both Valens and Richardson were sick.
So Jennings agreed to give up his seat to Richardson and take the bus instead.
Holly joked to him that he hoped their bus broke down, to which Jennings replied, quote,
"I hope your ol' plane crashes."
Horrifyingly, that's exactly what happened.
Everyone on board, Richardson, Holly, Valens, and pilot Roger Peterson, were thrown from
the plane when it crashed shortly after liftoff, and none survived.
"Never a week goes by when I don't think of something about it and those guys."
Waylon Jennings' love life is synonymous with his long relationship with Jessi Colter, whom
he married in 1969.
She's the mother of his most famous kid, Waylon Albright Jennings, aka indie country star
Shooter Jennings.
While it was happily ever after for Jennings, things weren't so smooth in his early years.
Waylon was married, and divorced, on three previous occasions.
His rocky personal life took a toll.
Jennings told 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."
Waylon Jennings certainly did his fair share of hard living, but in 1972, the 35-year-old
singer got extremely sick and could've died after just having a slice of pie and a glass
of milk.
Jennings wrote in Waylon: An Autobiography that he only remembered afterwards that he
had been warned not to eat anything local during his tour due to a hepatitis outbreak.
Unfortunately, it was too late.
Within a couple days he was experiencing back and kidney pain, and his wife noticed he looked
yellow, a telltale sign of hepatitis.
Though he initially refused any treatment, after passing out he finally agreed to seek
potentially life saving treatment at a nearby hospital.
In the 1970s and 1980s, according to People, Waylon Jennings was gripped by a powerful
addiction to cocaine.
It got so bad that he and his wife Jessi Colter briefly separated.
Not even an August 1977 bust by police at a Nashville recording studio, where he had
so much cocaine on his person that he was charged with intent to distribute, could get
him to quit.
The effects of the drug seemingly hadn't affected his work, though...until a 1984 show in Portland,
Oregon, when he mumbled his way through just a few songs and stumbled off the stage to
a chorus of boos.
That spurred him to seek help.
At the suggestion of Johnny Cash, he tried the Betty Ford Center; though he wasn't able
to completely kick the habit there, it helped inspire him to finally go cold turkey once
and for all, after flushing $20,000 worth of cocaine down the toilet.
As a major singer-songwriter, recording artist, and concert draw throughout much of the latter
half of the 20th century, Waylon Jennings made a lot of money.
Unfortunately, he also blew through that money almost as fast as he made it.
According to his autobiography, Jennings went broke no less than three times.
At one point, his home and other real estate holdings were seized, his bank accounts had
been closed, and his advances were all spent.
He attributed part of that to a $1,500 a day drug habit, and part of it to paying a huge
staff that included,
"...a road manager, a band manager, a publicist, a secretary, a booking agent, a receptionist,
gofers, and personal assistants all around."
In 1981, Jennings had to even file for bankruptcy, citing a whopping $2.5 million in debt.
Cocaine is very bad for the heart.
And although Waylon Jennings stopped using the drug in 1984, he still endured heart troubles
many years later.
In October 1988, doctors performed a balloon angioplasty to clear a blocked artery.
Just two months later, while on his tour bus and headed to a gig in Tennessee, a 51-year-old
Jennings started to suffer from chest pains so intense that his driver immediately re-routed
to Baptist Hospital in Nashville.
Tests revealed partial blockage in three of Jennings' arteries, necessitating immediate
triple-bypass surgery.
Fortunately, at no point did he suffer a heart attack, and he made a full recovery.
Under doctors' orders of rest and relaxation, Jennings canceled two months' worth of shows,
and he also had to adopt healthier habits, and fast.
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."
Cocaine discourages appetite, and at his lowest points, Jennings was almost skeletal, subsisting
on milkshakes force-fed to him by wife Jessi Colter.
But after he quit the drug, his appetite returned full force, and Jennings quickly began putting
on pounds, writing that, quote, "once I started gaining weight, I couldn't stop."
Less than a decade after finally shaking his drug habit, Jennings was diagnosed with adult-onset,
or type II diabetes, which can lead to severe complications, including kidney problems,
vision loss, and poor circulation.
Sadly, Jennings developed vascular disease in both legs.
In 2001, he got an infection in his foot, and his body, ravaged by diabetes, couldn't
fight it off.
Doctors had to amputate it to try and save his life, but it was too late; just two months
later, the country legend passed away at age 62.
But his legacy will always be around.
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