In 1988 The Traveling Wilburys introduced the pop world to the idea of a super group of well known artists from other bands, collaborating on a single album. Three years before The Traveling Willburys unleashed their first album though, The Highwaymen did the same service for the Country Music world.

Johnny Cash, Willie Nelson, Waylon Jennings and Kris Kristofferson had been friends for years and had collaborated together in a variety of combinations before they decided to come together for the 1985 self titled single The Highwaymen. With over a century of combined experience in the music world and representing four powerful portions of the industry, a hit was almost guaranteed.

The Highwaymen is an almost folksy song, wherein each member sings several verses in turn and they all join in for the chorus. The song itself implies that each member of the group is an immortal, or that each represents a particular "life" of a single immortal person. The stanzas they sing recount an adventure they had experienced and seem mournful of the past while still hopeful for the future as they tell us in the chorus “I'll always be around, and around, and around..."

Nelson's stanza recounts his life as the titular highwayman, "along the coach roads I did ride, Sword and pistol by my side." A lifestyle that Nelson paints with romance and then notes "The bastards hung me in the spring of 25."

Kristofferson regales the audience with a stanza about his life as a sailor "I was born upon the tide, with the sea I did abide" evoking an image of a lonely and hard life ended by an apparent accident. "When the yard broke off they say that I got killed, but I am living still."

Jennings' tale is that of a dam builder working on the colossal Boulder Dam (latter renamed Hoover Dam). "Where steel and water did collide, A place called Boulder on the wild Colorado." Jennings' stanza, while fitting with the theme, is of note because it reinforces an oft quoted myth that there are men buried in the still setting cement of the Hoover Dam, "I slipped and fell on the wet concrete below, They buried me in that gray tomb." In fact, the damn was poured in shallow enough sections that anyone who fell could have simply stood up.

Cash's stanza, while as musically apt as ever, has always struck me as an odd bit. Cash, in a departure from country music themes, tells us about his role as pilot of a space ship, "I'll fly a starship across the universe divide." In an otherwise excellent song, I'm saddened to report that Cash's contribution is the one that destroys the illusion for me. His selection of a starship pilot seems out of character for a country song and especially so in comparison to the other three stanzas and their rather typical themes.

The single climbed the Country Music charts and was such a success that an entire album was written and released before the year was out with the same title as the single. The album had another top 20 hit with a cover of Guy Clark's Desperadoes Waiting For a Train. After a tour the four members each returned to their respective solo careers for a number of years before returning with their sophomore effort, the unoriginally titled Highwaymen 2 in 1990. Fortunately the album was a tad more creative than the bland title, and although it had a mild hit with Silver Stallion, it wasn't nearly as successful as its predecessor.

After another hiatus the foursome returned with a new contract, and album, in 1995 with The Road Goes on Forever. The album was not a success, either creatively or financially and unfortunately they did not record again before Jennings' death in 2002. When Cash died the following year any chances of rekindling the creative success of the first album evaporated.

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Lyrics by Cash/Jennings/Kristofferson/Nelson 1985