The Highwaymen: Outlaws United. In the annals of country music history, few collaborations have captured the imagination quite like The Highwaymen. Comprised of four of the genre's most iconic figures - Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson - this supergroup represented the pinnacle of outlaw country music and left an indelible mark on the landscape of American music. The Formation of a Legend The story of The Highwaymen begins in 1984, when Johnny Cash invited Willie Nelson, Waylon Jennings, and Kris Kristofferson to join him in Montreux, Switzerland, to film a televised tribute to Cash's 30-year career. The chemistry between these four legends was immediately apparent, and it wasn't long before the idea of a collaborative project began to take shape. The group's name was inspired by the Jimmy Webb-penned song "Highwayman," which tells the story of a soul with incarnations in four different places in time and history. This song would become the title track of their first album and a signature piece for the supergroup. The Titans of Outlaw Country Before delving into the group's work, it's important to understand the individual legacies that each member brought to The Highwaymen: Johnny Cash: Known as "The Man in Black," Cash was already a country music icon by the 1980s. His deep, distinctive voice and rebellious image had made him a crossover star, appealing to country, rock, and folk audiences alike. Willie Nelson: With his unmistakable voice and unconventional approach to country music, Nelson had become one of the most recognizable figures in the genre. His album "Red Headed Stranger" is considered a landmark in outlaw country. Waylon Jennings: A pioneer of the outlaw movement in country music, Jennings was known for his rough-edged voice and his resistance to the polished Nashville sound. Kris Kristofferson: A Rhodes Scholar turned songwriter and performer, Kristofferson brought a poetic sensibility to country music. His songs had been recorded by numerous artists, and he had also found success as an actor. Each of these artists had played a crucial role in the outlaw country movement of the 1970s, which rebelled against the slick, produced sound of mainstream country music in favor of a rawer, more authentic approach. The Albums The Highwaymen released three studio albums over the course of their collaboration: "Highwayman" (1985): The group's debut album was an immediate success. The title track, "Highwayman," reached No. 1 on the Billboard country music charts and won a Grammy for Best Country Song. Other notable tracks included "Desperados Waiting for a Train" and "Big River." "Highwayman 2" (1990): This follow-up album featured songs written by all four members, as well as covers of songs by other artists. Standout tracks included "Silver Stallion" and "Born and Raised in Black and White." "The Road Goes on Forever" (1995): The group's final studio album showcased their evolving sound and continued col...