The Highwaymen Biography

The Highwaymen Biography

The Highwaymen were a country supergroup comprising four musicians well known for, among other things, their involvement and pioneering influence on the outlaw country subgenre: Johnny Cash, Waylon Jennings, Willie Nelson and Kris Kristofferson.  Outlaws and good old boys Jennings and Cash had worked together previously and had great respect for each other; Jennings was a good friend of Cash's, the latter calling him his "blood brother." The two would go on to release a collaborative effort entitled Heroes in 1986. Cash had also arguably jump started Kristofferson's career by promoting him and one of his most well-known songs, "Sunday Mornin' Comin' Down", famously covering the latter. Nelson had also worked with Jennings on three previous albums: 1978's Waylon and Willie, 1982's WWII and 1983's Take It to the Limit, and with Kristofferson on the 1982 album The Winning Hand with Dolly Parton and Brenda Lee. Though Cash and Nelson hadn't had much contact prior to the group's formation, there was mutual respect between them; notably, they would release the live VH1 Storytellers album together in 1998. While Kris Kristofferson was perhaps lesser known for his participation in the outlaw country movement popularized by Nelson and Jennings, he was prominent on the Austin music scene during its 1970s heyday and included in the Highwaymen as a mark of his musical collaborations with and contributions to the others in the group.

Formed in 1985, the group released an album that same year entitled Highwayman, which followed the success of their #1 country hit, "Highwayman", a Jimmy Webb cover, and also spawned a Top 20 single, Guy Clark's "Desperados Waiting for a Train". At the time, the group did not have an official name and the album was credited to "Nelson, Jennings, Cash, Kristofferson". Produced by Chips Moman, Highwayman was released by Columbia Records.  In 1990, the group reunited for a second effort, simply entitled Highwayman 2, which did not repeat the success of their first album, but still became rather popular, reaching #4 on the country album charts, with the Lee Clayton-penned song "Silver Stallion" as the first single and a minor hit which made the country Top 40. The album was nominated for a Grammy for Best Country Vocal Collaboration. Highwayman 2 was produced, once again, by Moman. Six of the songs were written by, or in collaboration with, members of the group.  The group's final release prior to Jennings' death in 2002, was 1995's Don Was-produced album The Road Goes on Forever (a Robert Earl Keen, Jr. cover), and its single, "It Is What It Is", both of which went by relatively unnoticed. The four singers then returned to their solo careers, though a tenth-anniversary edition of The Road Goes on Forever appeared in 2005, with several raw bonus tracks added as well as, in some versions, a DVD containing the music video for "It Is What It Is" and a documentary entitled Live Forever - In the Studio with the Highwaymen.