In 1985, Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson formed the
country music supergroup The Highwaymen. Over the next ten years and three albums, they
thrilled fans around the globe. Then they vanished like ghost riders in the sky. Here's
the untold truth of The Highwaymen.
Country music fans got the gift of a lifetime for Christmas in 1984, but it didn't come
from Santa Claus - it came from Marty Stuart.
At the time, Stuart was working with Johnny Cash's band, so he was on hand in Switzerland
for the filming of a Johnny Cash Christmas TV special that also featured Willie Nelson,
Waylon Jennings, and Kris Kristofferson as special guests.
Back at the hotel, they got to jamming and hanging out, and realized it would be fun
to team up and try something new. It was also a second chance for Cash, who had been on
a career downswing and was feeling low as a result. Stuart, who was also Cash's son-in-law
at the time, said that the idea of a supergroup was Johnny's, quote, "first glimmer of hope"
in a while.
But with four distinct singing voices, harmonizing proved difficult at first, especially between
Cash and Nelson, who initially tried to record a duet album with little success. Luckily,
Stuart had an idea, and brought them the song "Highwaymen" to cover.
"I said, listen, four verses, four guys, no harmony required."
According to Stuart, Cash liked it, as long as he could sing the verse about the starship.The
four country icons recorded "Highwayman," and it went on to be the supergroups only
No.1 single, winning the Grammy Award in 1985 for Best Country Song.
In 1985, when the country legends released the album "Highwayman," the supergroup had
yet to officially name themselves. Instead, they simply listed all four of their individual
names along with the album title.
When they went on tour in 1990, though, they needed a name for the group, which is when
they decided to adopt the name Highwaymen from their hit song and album.
Just one problem: there was already a group called The Highwaymen. A folk group from the
late 1950s and early 1960s, the original Highwaymen didn't appreciate their name being taken and
filed a lawsuit.
According to the Willie Nelson and Friends Museum, things were quickly smoothed over,
and the folk group dropped the lawsuit in exchange for the opportunity to open for the
new Highwaymen at a Los Angeles concert.
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,
"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..."
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."
There was one other buddy who was nearly in the group as well. In 2015, country legend
Merle Haggard, who was close friends with all the members of the Highwaymen, revealed
that they had asked him to join the group. Unfortunately for country music fans, though,
he declined the offer.
The four members of The Highwaymen were like brothers — and like brothers, that meant
that they sometimes fought with each other.
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. They were like brothers up there, bickering
with each other."
According to The Los Angeles Times, another point of contention was the political activism
of Kris Kirsotfferson, whose views were often at odds with the more conservative Waylon
Jennings. And Jennings didn't really appreciate Kristofferson bringing his political agenda
onto the stage, as he didn't think it had a place in entertainment.
Jessi Colter, Jennings widow, spoke to Rolling Stone about it.
"Kris was very much into politics. 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."
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, officially
ending the Highwaymen's run. Cash’s death was soon to follow in 2003. At 71, he also
succumbed to health problems related to diabetes.
Columbia/Legacy released a Highwaymen box set in 2016 called "The Highwaymen Live — American
Outlaws" that compiled some of their most memorable live performances. And in the PBS
film "The Highwaymen: 'Friends Till the End'", Nelson and Kristofferson spoke about what
their time with the Highwaymen meant to them. Kristofferson said,
"For me, it was heaven. 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.
"I had three of my favorite people out there. 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."
"These were some of the best times of my life."
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