The Highwaymen: country’s attempt at The Traveling Wilburys
Contrary to what we might think, the world doesn’t automatically reward supergroups. Despite the success of the likes of the Marvel Cinematic Universe, Real Madrid’s Galácticos, and, perhaps more modestly, The Traveling Wilburys, sticking famous and talented people together isn’t a surefire hit.
A point made even more pertinent when considering the famously gruff and uncompromising Bob Dylan was a key member of The Traveling Wilburys. Along with George Harrison, Roy Orbison, Tom Petty and Jeff Lynne, the band struck a quick lightning rod through the music industry with two swift records that nonchalantly displayed their undeniable brilliance before the death of Orbison.
Because of Orbison’s passing, the band scrapped some of their ambitious plans to play live, leaving a window of opportunity for the next supergroup to jump in through. While The Traveling Wilburys was a project built on each of the players’ innate artistic desire to create something fresh, the premise of glueing some of the industry’s finest players together projected dollar signs in the eyes of label executives.
While many tried to emulate The Wilburys’ touch for those very reasons, one band emerged with an equal level of prestige to try and usher in the dawn of the next great supergroup chapter. Kris Kristofferson, Waylon Jennings, Johnny Cash, and Willie Nelson joined forces in 1985 to give country music their own powerhouse under the name The Highwaymen.
“It came out of pure friendship,” Johnny Cash’s daughter, Rosanne, said. “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.”
Their debut album sold over a million copies, and the title track, ‘Highwayman’, reached number one on the Billboard country charts. And they managed to do something The Traveling Wilburys couldn’t—head out on their own. Onstage, the Highwaymen’s live shows were a greatest hits medley, with each member taking a turn in the spotlight to play their hits. “You had Cash doing ‘Big River’ and then Willie doing ‘Always on My Mind’. It blew people’s minds,” said Jennings.
In the case of Jennings, it was just about getting together and playing good old country music to a wanting crowd. Sets could ebb and flow between their own work and that of the group but whatever happened, the main aim was to get a warm round of applause. But the harmoniousness of that journey was sometimes challenged by Kris Kristofferson.
“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,” says Jessi Colter, Jennings’ widow. “It was a loving thing when Kris and Waylon got together, but onstage, when Kris would talk politics, Waylon wouldn’t agree.”
Perhaps the smaller cultural footprint of the country’s attempt at a supergroup is firmly rooted in the genre’s smaller level of popularity. But whatever you say about The Highwaymen, the very fact fans got to see the supergroup share the stage is the one triumph The Traveling Wilburys can’t top.
