Fri. Jun 9th, 2023

It is always an intriguing experience when a combination of tremendous musical minds come together in order to create a supergroup. The Travelling Wilburys and Cream come to mind as rock’s greatest examples of this concept. For the genre of country, however, The Highwaymen take the top tier as the prime example of an all-star cast coming to work together for a short time. Composed of Kris Krisofferson, Waylon Jennings, Willie Nelson and Johnny Cash, The Highwaymen released their first of three original albums in 1985. Most of the ten tracks were covers of previously recorded pieces written by other artists of the era including Bob Seger, Woody Guthrie and more. The album was an instant hit following the success of the title track in the charts. At the time, country music was making a shift to a new sound, and though change is good in its own right, these four legends looked back upon the past with an unrivaled nostalgia that culminated in a supergroup formulation for the ages.

Originally written by Jimmy Webb, “Highwayman” kicks off the album with a story about four different characters being a part of the same travelling soul. The iconic flute introduction backed by acoustic guitar backs all four Highwaymen voices. Willie Nelson takes the first verse as he embodies the original highwayman, a bandit notorious for his ruffian lifestyle who met his end when the law finally caught up. Kristofferson takes on the next voice as the second destination for the highwayman’s soul as a sailor killed while travelling the seas. Jennings chimes in as the dam builder who slipped, fell and died in an accident sending his soul to another destination. That destination ends up being Johnny Cash’s “starship” captain who speaks of the search for another “place to rest [his] spirit.” Webb, when addressing the group’s cover of his song, spoke of Cash’s entrance as the feeling of hearing the “voice of God” sing the part. This comment speaks volumes of the esteem held for the ‘man in black’ by those of the country world. 

The next piece is called “The Last Cowboy Song” written by Ed Bruce and Ron Peterson. All four Highwaymen sing this tale of the legend of a cowboy making his way in the history of the great wild west. It weaves a story of the final ‘cowboy’ spirit that used to exist in the spirit of those in the old west. 

The third track is a mournful tune of the narrator bidding a farewell to his friend, Jim. In “Jim, I Wore a Tie Today” we hear of the funeral for the recently deceased friend of the narrator. Nelson and Cash sing this longing song telling Jim about how missed he is and the memories of their adventures together that come across the narrator’s mind during the funeral. 

Offering a contrast to this song of farewell is a bumpy Johnny Cash tune called “Big River.. The tale is of a man missing his love and searching for her as she moves on with the metaphorical ‘big river’ rather than stay with him. It’s about the difficulty in the decisions many people make when they decide to live life to the fullest, in contrast to if they were to stay and settle down. This version includes an extra verse that Cash had not included in his original release back in 1958.

The next track is again one previously written by Cash. It documents several members of a mental institution through the eyes of a new member. Cash himself dealt with struggles to overcome addiction and through those experiences he developed a piece to recognize those who suffer from worse mental conditions. 

The next piece was written by Guy Clark telling the story of a “sidekick” to a famous cowboy in the old west. “Desperados Waiting For a Train” follows a boy growing up by the side of a mentor and father-like figure until he is near death and the boy has grown up. 

Featuring guest singer Johnny Rodriguez, “Deportee (Plane Wreck at Los Gatos)” takes up the sixth slot on the album. Written originally by Woody Guthrie, this song tells the tragic true story of the Los Gatos plane crash in 1948. About thirty-two people, mostly farm laborers from Mexico, were killed in a plane that was taking the people back to Mexico. It relays the painful message that those killed lost their identities and were remembered by only their title of “deportees.” 

The eighth track, called “Welfare Line,” was originally written by Paul Kennerly. It explores the memories of a man who lived an adventurous life which saw him serving on the battlefield to being a part of a gang of bandits. He recalls these adventures with his friends in this nostalgic piece. 

One of the most famous pieces on this album gets its recognition from its original writer: Bob Seger. “Against The Wind” is the ultimate tale of how age correlates to the responsibilities of life. The narrator, sung by Cash, Nelson, and Jennings, lives life freely and goes “against the wind” in the sense that he abides not by the chains of responsibility but by the direction his soul takes him along with the “love of his life.” Eventually “deadlines and commitments” catch up with them and the responsibilities of daily life bear their weight upon them as they remain, though older, fighting “against the wind.” 

The final piece was written by Steve Goodman and John Prine. “The Twentieth Century is Almost Over” is a reflective tune about the fading history as the century nears its end. Sung by Cash and Nelson, this piece again encapsulates the theme of this album: while change is good, it is vital to remember the past to build a greater future. That theme is prevalent in the reason this group initially formed and is present in almost every song in some way. Today, only two of the Highwaymen remain alive as Jennings and Cash both died years ago. Yet, the legacy that each of them left behind — in this group and by themselves — is among the greatest musical treasures to discover. 

Joseph Gill is a first-year English major in the writings track. 

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