Willie Nelson, Waylon Jennings, Johnny Cash and Kris Kristofferson were some of the best-known outlaws in country music history, and to hear them tell it, they had some hefty experiences with drugs and alcohol over the course of their careers, both independently and together.
So when the foursome toured together as supergroup The Highwaymen in the 1980s and 1990s, many fans might envision backstage parties filled with alcohol, weed and pills.
But a list of the group’s tour rider paints a much more wholesome picture.
A tour rider posted to Cash’s social media lists each bandmate’s requests for food and drink in their dressing rooms after a show — and, well, as the post puts it, they’re “simple requests.”
All four Highwaymen asked for fruit backstage, plus spring water and some form of coffee (hot for Cash, Nelson and Jennings, iced for Kristofferson). Cash and Kristofferson also enjoyed fruit juice backstage.
Each of them also included 12 sodas on their tour rider: Everyone wanted Coca-Cola, and three out of four specifically wanted some Diet or caffeine-free Cokes.
Nelson’s the only one who mixed it up with another drink: In addition to six Cokes, he wanted six 7-Ups.
It’s a far cry from the hard-partying lifestyles fans might associate with these country superstars. Not only did Jennings request caffeine-free and diet soda, but he even drank skim milk in his coffee.
Of course, it’s entirely possible that the singers packed their own alcohol to mix with their diet, caffeine-free Cokes. But it’s also possible that their backstage refreshment habits really were that simple.
All four of The Highwaymen struggled with substance abuse at some point in their lives, and they’ve been open about it. At the time they toured together, all four band members were in varying stages of estrangement from alcohol.
Kris Kristofferson Started a Sobriety Journey in the Mid-1970s
Early on in his career, Kristofferson was a self-described functioning alcohol, and he didn’t think he’d live past 30. But in 1976, the singer played the main character of John Norman Howard in A Star is Born.
Spoiler alert: His character dies after driving drunk and wrecking his car, and his love interest Esther tends to his dead body.
Read More: The Stunning Reason Why Kris Kristofferson Quit Drinking
Kristofferson said that scene was so powerful, it inspired him to quit drinking in real life.
“I remember feeling that that could very easily be my wife and kids crying over me,” he told People in 1998. “I quit drinking over that. I didn’t want to die before my daughter grew up.”
So Kristofferson wouldn’t have been drinking when The Highwaymen toured in the ’80s and ’90s — he’d already been sober for years by that point.
Waylon Jennings Never Really Drank That Much in the First Place
Did “this outlaw bit done got out of hand“? Sure did, when it comes to Jennings’ reputation as a drinker.
In a 1988 interview with Spin, the singer admitted that he’d never been much for alcohol. He still had a well-earned reputation as a hard partier, though, due to his fondness for another addictive substance: Cocaine.
“I never did drink. That used to be one of my big brags. I would sit around and say, ‘I don’t drink and I never did drink,'” Jennings recounted. “There I’d be just stoned out of my gourd on cocaine, but I was real proud of myself because I never did drink.”
The singer’s drug habit became public knowledge in 1977 when he got arrested at a Nashville recording studio and charged with conspiracy and possession of cocaine with intent to distribute. He’d later go on to quit the habit cold turkey in 1984, a year before the Highwaymen formed.
Willie Nelson … Well, You Already Know Willie Nelson’s Drug of Choice
Nelson is still known today for how much he enjoys marijuana. Save Snoop Dogg, no other celebrity is more closely associated with the plant. The country legend even has his own line of CBD and THC-infused products called Willie’s Reserve.
Nelson used to drink heavily, and he credits his THC use with his ability to give up alcohol many years ago.
“Well, [marijuana] not only saved my life, it probably saved some other people’s lives,” the singer told E! News in 2023. “Because before I smoked marijuana, I was drinking a lot. And I might have killed a lot of people, too. So I’m just glad that that didn’t happen. I’m glad we live through all of bad times.”
Johnny Cash Was Still Fighting His Addictions During The Highwaymen’s Reign
Out of the four artists, Johnny Cash was the only Highwayman who might still have been in active alcohol addiction during the time when the group was touring.
The singer struggled with alcohol during his career, but perhaps his biggest fight was with pills: Both amphetamines and sedatives.
Throughout the ’80s, Cash quit multiple times, with help from rehab stays and the support of his wife, June Carter Cash. But he always relapsed, until he finally quit for good in 1992. That means that he was still fighting addiction during The Highwaymen’s time on the road, but he was having stints of sobriety at that point, too.
18 Country Artists Who Are Sober
Although country music is known for its raucous drinking songs, several artists have sworn off the stuff completely. Be it a lifestyle change or a life-saving decision, each one of these artists can say that that their lives have changed for the better since giving up the bottle. They are sober and proud.
