The Highwaymen band members include Kris Kristofferson, Wille Nelson, Johnny Cash, and Waylon Jennings. The Highwaymen was formed in 1985.
Formed in 1985, the band comprised four of country music’s biggest artists. Though they disbanded officially on February 13, 2002, the band was only active for ten years from 1985 to 1995.
Throughout their ten-year career as a band, The Highwaymen released three albums named Highwaymen in 1985, its sequel, Highwaymen 2, in 1990, and their last album, The Road Goes on Forever, in 1995.
They also released an archival live album in 2016 called The Highwaymen Live: American Outlaws. Lastly, the band starred in a movie together called Stagecoach which came out in 1986.
Sadly, two of the band members have passed away. Jennings on February 13, 2002, and Cash on September 1, 2003.
1. Kris Kristofferson
The Highwaymen band members include Kristoffer Kristofferson. He is best known as Kris Kristofferson.
Kristofferson is a celebrated actor, musician, and songwriter who has been active in all three fields from 1959 up to his retirement in 2020.
Early Life
He was born on June 22, 1936, in Brownsville, Texas, and has Swedish, English, Scots-Irish, German, Swiss-German, and Dutch ancestry. He was born to Mary Ann Ashbrook and Lars Henry Kristofferson who was an officer in the U.S. Army Air Corps.
The singer’s youth consisted of moving around frequently due to his father’s military service. However, they finally settled in San Mateo, California, where he attended San Mateo High School.
The boy would graduate from the school in 1954 and enroll in Pomona College immediately to pursue his dreams of being a writer. His early stories “The Rock” and “Gone Are the Days” would get published in The Atlantic Monthly.
These early writings would also show the concerns he would end up writing about throughout his life in the form of geography and racial disharmony. Sadly, the future singer would end up joining the army after college due to pressures from his family.
He would eventually attain the rank of captain while in the army and even stationed in West Germany. However, the army never fit him and he would leave the army in 1965 and was disowned by his family.
Success
In 1965, he would move to Nashville though it would take him five years to release his debut album, Kristofferson in 1970. He would end up releasing 26 albums in total throughout his career.
He would also start his equally successful film career a year after his debut album’s release in 1971 with his role as Minstrel Wrangler in The Last Movie. The singer would see a total of 121 acting credits in his career.
Celebrated in both fields, Kristofferson has won many awards, with his most prestigious being a Golden Globe Award in 1976 and four Grammy Awards in total.
2. Willie Nelson
Willie Nelson played the vocals, backing vocals, and the guitar in The Highwayman. He is one of the most successful country singers of all time.
Early Life
Born on April 29, 1933, in Abbott, Texas, Nelson was born to Mryle Marie and Ira Doyle Nelson. Sadly, his mother would leave soon after he was born and his father would leave him and his sister Bobbie to be raised by grandparents after getting remarried.
Success
Despite early parental misgivings, Nelson would go on to have a highly successful career, and many see him as one of, if not the main figure in a subgenre of country music called outlaw country.
Outlaw country is a subgenre of country music that carries an anti-establishment message and champions creative freedom. Like the genre he is the face of, Nelson has spent his life singing about and fighting for his progressive ideals, making him a seminal if controversial figure in country music.
In a career that spans more than half a century, the singer has released over 128 albums spanning from 1962 to 2023 with his most recent album, I Don’t Know a Thing About Love: The Songs of Harlan Howard set to release on March 3, 2023.
Acting Career
Few can rival Nelson in musical productivity, and few have even tried. Music isn’t his only art form as Nelson, like his previously mentioned bandmate Kris Kristofferson, has also had a long and varied acting career.
His first role was in 1979 as Wendell Hickson in the movie, The Electric Horseman. Since then, the actor has appeared in 75 acting projects with the most recent one coming out in 2022.
The singer has garnered over 109 nominations in total just for his acting and has won 48 times. As for his music, the singer has won 37 in total which includes an impressive 15 Grammy Awards, 8 American Music Awards, 10 Country Music Association Awards, and 5 Academy of Country Music Awards to name a few.
3. Johnny Cash
Johnny Cash was an American country singer-songwriter. He also played vocals, backing vocals, and the guitar for The Highwaymen.
Arguably the most popular member of the group, Cash is known internationally as the most important, or at least the most popular, figure in country music in the 20th century. He is best known for his deep voice, poetic lyrics, and somber but humble demeanor.
He is also considered iconic for his all-black stage wardrobe due to which he became known by the respected nickname, The Man in Black. He stated in a song of the same name that he liked to wear all black in mourning for all the poor and oppressed people in the world.
Early Life
The singer was born on February 26, 1932, in Kingsland, Arkansas. He was born to Carrie Cloveree Rivers and Ray Cash. He has six siblings in total with three, Roy, Margaret Louise, and Jack being older, and three, Reba, Joanne, and Tommy being younger.
His family were cotton farmers and very poor, and the singer worked in cotton fields starting from the age of five. Tragedy struck them early on when his older brother Jack, whom Cash was very close to, died due to a freak table saw accident in 1944.
Cash has famously felt very sad and guilty about the event, and has stated that he decided to be successful not only for himself but for his brother, Jack. He learned how to play guitar from his mother and started writing songs at the age of 12.
Success
He started his musical career in 1954 when he and his first wife Vivian moved to Memphis, Tennessee. He would start selling records a year later with his recordings of “Hey Porter” and “Cry! Cry! Cry!”
Cash would go on to have a successful career with over 80 albums to his name. Like Nelson, his success and productivity would carry on to his old age as the artist was still releasing music right up to the moment he passed away on September 12, 2003, due to complications from diabetes.
4. Waylon Jennings
Waylon Jennings is an American singer, songwriter, actor, and musician. He was the first member of The Highwaymen to pass away.
Early Life
Born on June 15, 1937, in Littlefield, Texas, Jennings’s parents are Lorene Beatrice Shipley and William Albert Jennings. His heritage is Irish and Black Dutch.
Like Cash before him, Jennings was also taught how to play the guitar by his mother. She taught him how to play the instrument when he was 8 by teaching him the tune of “Thirty Pieces of Silver.”
In his early years, the singer would practice with relatives’ instruments until Lorene bought a used guitar. During his early years, Jennings would be influenced by Carl Smith, Elvis Presley, and Hank Williams to name a few.
Success
Jennings’s beginnings in country music were the easiest when compared to his fellow bandmates. He auditioned for a spot on KVOW in Littlefield, Texas at the age of 14.
He and his band were hired to play for the show. Though his style, which was a mixture of Country, Western, and Bluegrass music, wasn’t well-received, Jennings would slowly start a career in country music.
In a career spanning fifty-two years, Jennings released 60 albums in total either by himself or with many of Cash, Nelson, or Kristofferson. Like his bandmates, he would also act occasionally, but he never tried to make a career out of it like them.
Sadly, Jennings passed away on February 12, 2002 from complications from diabetes brought about by a life of heavy smoking and drug use. With his death, The Highwaymen officially ended.