The Highwaymen were a supergroup made up of the cool guys of classic country: Willie Nelson, Johnny Cash, Waylon Jennings and Kris Kristofferson. The four prolific singer-songwriters shared a friendship and a love for music that translated into three albums over 10 years from 1985 to 1995: "Highwayman," "Highwayman 2," and "The Road Goes On Forever."
By the time Waylon, Willie, and the others decided to join forces, each already had long, successful careers under their belts and a string of hits that are still beloved classics today. Yet as a group, they only had one No. 1 single, and none of them even wrote it.
The song "Highwayman" was written by Jimmy Webb and had been recorded and played live by Glen Campbell. However, as country musician Marty Stuart tells it, he presented Cash with the song as a way to illustrate how the four men could collaborate, according to "Classic Country Music."
A TV Christmas special led to the formation of The Highwaymen
To back up a little bit, it wasn’t Stuart’s idea that Cash, Nelson, Jennings, and Kristofferson form the Highwaymen, but he was an early cheerleader.
According to the Willie Nelson and Friends Museum, the idea for the four men to collaborate came in 1984 when Cash enlisted the three musicians to play on his Johnny Cash Christmas TV special that was filmed in Switzerland. Back at the hotel, they got to jamming and hanging out and realized it would be fun to team up and try something new.
But there was a little something else. According to Classic Country Music, Cash had been bummed around that time because his newer music wasn’t doing as well as it did in earlier years. Stuart, who was Cash’s son-in-law at the time, said Cash got his "first glimmer of hope" while in Switzerland playing with Jennings, Nelson, and Kristofferson.
But with four distinct singing voices, specifically between Cash and Nelson, harmonizing proved difficult at first. Stuart said he got the idea for the quartet to cover "Highwayman."
He brought it to Cash and said, "Listen, four verses, four guys, no harmony required."
Cash liked it, as long as he could sing the verse about the starship, Stuart recalled. The friends recorded "Highwayman," and it went on to be the supergroups only No.1 single. The song also won a Grammy Award in 1985 for Best Country Song, per AllMusic.
The group didn’t use the name Highwaymen until 1990 and almost got sued
In 1985 when the country legends released the album "Highwayman," the supergroup had yet to name themselves. According to the Willie Nelson and Friends Museum, the fellas simply listed their names: Waylon Jennings, Willie Nelson, Johnny Cash, and Kris Kristofferson.
The group didn’t start touring until 1990, and it was then that they took the name, Highwaymen, from their hit song and successful 1985 album, per the Willie Nelson and Friends Museum.
But a boss name like that was already spoken for. A folk group from the late 1950s and early 1960s called The Highwaymen didn’t appreciate their name being taken and filed a lawsuit. The situation was easily smoothed over though, when according to the Willie Nelson and Friends Museum, the folk group dropped the lawsuit in exchange for the opportunity to open for the new Highwaymen at a Los Angeles concert.
Johnny Cash and Willie Nelson weren’t that well acquainted prior to 1984
While the Highwaymen are often thought of as four buddies who liked to play music together, in reality, Cash and Nelson didn’t really know each other that well prior to the Christmas special.
According to Classic Country Music, Stuart explained, "And what was interesting was that John and Willie didn’t know each other really. John and Waylon were close, John and Kris were close, Kris and Willie were close, Waylon and Willie were close, but John and Willie were like this…" and he moves his fingers to signify being in proximity to each other but not interacting.
Cash’s daughter and musician in her own right, Rosanne Cash, told Rolling Stone in 2016 that the Highwaymen "came out of pure friendship. There was no marketing guy who came and said, ‘This will be a good idea.’ My dad and Waylon were roommates in the ’60s, hiding their drugs from each other. Kris is like his little brother for decades. … They were all buddies, and they wanted to do it."
While the Highwaymen were a supergroup of four incredibly talented and influential musicians, it could’ve been a group of five. Per Willie Nelson and Friends Museum, Merle Haggard said in 2015 that Nelson, Kristofferson, Jennings, and Cash asked him to join them early on, but he turned down the offer.
The Highwaymen were good friends but also had small conflicts
Yet as much as the musicians were great friends, they were still men with their own political opinions and egos, and conflict sometimes arose as it does in any close relationship.
Shooter Jennings, Waylon’s son, told Rolling Stone he remembers little skirmishes between some of the guys.
"My dad and Cash would get in a fight and not talk, or they’d get mad at Willie cause Willie had one more song than everybody else," he said. "They were like brothers up there, bickering with each other."
Another point of contention was between Jennings and Kristofferson, as Kristofferson had gotten political in the late 1980s, the Los Angeles Times reported, and he took it to the stage. Jennings felt like political stands were better left out of entertainment.
Jessi Colter, Jennings widow, spoke to Rolling Stone about it.
"Kris was very much into politics," Colton said. "Waylon never believed that you should use that platform of entertainment [for that], so that really chafed him, but he understood Kris, and Kris understood him …. It was a loving thing when Kris and Waylon got together, but onstage, when Kris would talk politics, Waylon wouldn’t agree."
All things come to an end
After the success of the Highwaymen’s first album in 1985, their 1990 release, "Highwayman 2," didn’t get the same commercial love as the debut album, AllMusic reported. Their 1995 album, "The Road Goes on Forever," saw even less success and was the last recording by the supergroup.
Jennings died in 2002 at just 64 years old of complications related to diabetes, ABC News reported, officially ending the Highwaymen’s run. Cash followed shortly after in 2003. At 71, he also succumbed to health problems related to diabetes, per the Tennessean.
Columbia/Legacy released a Highwaymen box set in 2016 called "The Highwaymen Live — American Outlaws" that compiled some of their most memorable live performances.
In the PBS film "The Highwaymen: ‘The Mount Rushmore of Country Music’", Nelson and Kristofferson talk about what their time with the Highwaymen meant to them.
"For me, it was heaven," Kristofferson said. "I was up there on stage with my heroes — the people that I worshiped … We did nothing we didn’t want to do. And we stood up for things we believed in. And it was a beautiful life that way."
Nelson said something similar.
"Well, I had three of my favorite people out there," he told PBS. "I love them all like brothers. We all got along good together, and we had fun together. We made a movie together. We toured the world a couple of times. And they’re just some of the best times in my life."