The Highwaymen were an American country music supergroup, composed of four of country music’s biggest artists, Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson who pioneered the outlaw country folk music. Johnny Cash died on September 12, 2003 at the age of 71, Waylon Jennings died on February 13, 2002 at the age of 64, Willie Nelson is still alive at the age of 86 and Kris Kristofferson is 83.
There was a collegiate folk group named The Highwaymen fraternity brothers who originated at Wesleyan University and they had a Billboard #1 hit in 1961 with ‘Michael Row the Boat Ashore’, a version of the African-American spiritual, folk work song that predates the Civil War, and another Top 20 hit in 1962 with ‘Cotton Fields’ which was written by American blues musician Huddie Ledbetter. ‘Michael Row the Boat Ashore’ sold over one million copies, and was awarded a gold record. In 1990, the members of the original group sued country music’s Highwaymen, made up of Willie Nelson, Waylon Jennings, Johnny Cash, and Kris Kristofferson over their use of the name, which was inspired by a Jimmy Webb ballad they had recorded in 1977, which Webb released on his sixth album El Mirage.
The Highwaymen vs. the Highwaymen was settled in court, by a suggestion that Jennings came up with. The original Highwaymen still perform occasionally and they continue to earn royalties from their songs through oldies reissues, so Jennings suggested that they give the original group the opening slot at one of the new group’s concerts, giving them a payday and an opportunity to promote their oldies ventures and everyone thought that was a good idea.
American singer-songwriter Jimmy Webb wrote the song ‘Highwayman’ about a soul with incarnations in four different places in time and history. This soul is a highwayman, a sailor, a construction worker on the Hoover Dam, and finally as a captain of a starship. The song was influenced by the real-life hanged highwayman Jonathan Wild, a London underworld figure who operated on both sides of the law, posing as a public-spirited crimefighter. The dam builder verse alludes to the deaths of over one hundred men during the construction of Hoover Dam near Boulder City, Nevada, although none of those deaths resulted in a person being encased in concrete.
The idea for the group Highwaymen came about in 1984 when Cash wrangled Nelson, Kristofferson and Jennings to film his Christmas special in Montreux, Switzerland. Cash, Jennings, Kristofferson, and Nelson opened this show with ‘On the Road Again’, Jessi Colter, Waylon’s wife and Jennings performed ‘Silent Night’, and Kristofferson did ‘Good Morning, John’. Anita Carter a member of the Carter family, John Carter Cash the only child of Johnny Cash and June Carter Cash, June Carter Cash, and Connie Nelson, Willie’s wife also appeared on this Christmas special. Inspired by the camaraderie in the hotel, where they’d jam after long days on the set, the artists returned to the States and entered the studio with producer Chips Moman, eventually taking Webb’s song ‘Highwayman’ as both their name and the title of the album.
Waylon Jennings first met Johnny Cash in the mid-sixties when they roomed together briefly renting an apartment in Nashville, a set-up Jennings likened to the original Odd Couple, where Waylon was supposed to clean up and John was the one doing the cooking. Cash was in love with June Carter at the time, but could not move in with her because her divorce was not final, so he rented a one-bedroom apartment in Madison which is just north of Nashville, so he could be close to her. In the mid-eighties, the Cash’s had a home called “Cinnamon Hill” on the Caribbean island of Jamaica, which Waylon and his wife Jessi often visited. Johnny Cash and Waylon Jennings released the country album Heroes together in 1986.
Waylon was the outlaw rebel/good ol’ boy with the rock‘n’roll attitude. Willie was the wise pot-smoking hippie guru. Kris was a Rhodes scholar and movie star who had scored several hits on the pop charts. John had seemingly been everywhere and done everything. Waylon probably had the best singing voice in the group. Willie was probably the best overall musician. Kris was undoubtedly the best songwriter and John was simply a living legend whom everybody knew. The four musicians starred in one movie together, the 1986 film Stagecoach, which was a remake of the classic 1939 film Stagecoach that starred John Wayne. Kris Kristofferson is the Ringo Kid, Willie Nelson portrays famous gunslinger and dentist Doc Holliday, Johnny Cash portrays Marshal Curly Wilcox and Waylon Jennings plays the gambler, Hatfield.
The group released three studio albums between 1985 and 1995 Highwayman (1985), Highwayman 2 (1990), and The Road Goes On Forever (1995) along with seven singles. When the Highwaymen performed concerts, they often mixed in their solo material with that of the group on stage. All four men had been friends for decades prior to their musical collaboration, and their friendships and occasional musical partnerships continued after the supergroup disbanded.
Although their album was called Highwayman, the group didn’t officially call themselves by that name for this record, as they cited their individual names on the disc. Highwayman was the group’s first and most successful album. This album featured 10 cover songs and two of these were covers of Johnny Cash songs. The single ‘Highwayman’ became a #1 country hit, it held on the Billboard charts for 20 weeks and went on to become a Top 5 song of the entire year. Their remake of Guy Clark’s ‘Desperados Waiting for a Train’ reached the Top 20. Johnny Cash and Kris Kristofferson sang while Willie Nelson and Waylon Jennings both sang and played guitars. Additional musicians included J. R. Cobb and Reggie Young who played guitars, Marty Stuart played guitar and mandolin and Chips Moman played guitars and sang background vocals. Both Mike Leech and Jimmy Tittle played bass guitar and Bobby Wood and Bobby Emmons played keyboards and Paul Davis played keyboards and sang background vocals. Gene Chrisman played drums, Mickey Raphael played harmonica and Johnny Rodriguez sang background vocals.
They followed it up with Highwaymen 2 in 1990 and this album spent 40 weeks on the country chart, peaking at number 4. This album contained 6 songs written by members of the group and four were covers. The Lee Clayton-penned song ‘Silver Stallion’ was the first single and it made the country Top 40. The album was nominated for a Grammy for “Best Country Vocal Collaboration”.
In 1995 they released their third and final studio album The Road Goes on Forever which peaked at #42 on the U.S. Billboard Top Country Albums chart. The Highwaymen hired Don Was to produce this album and he had previously worked with every member of the group except Johnny Cash, so he became the natural choice. This album has great material, from standards like Dallas Frazier’s ‘True Love Travels on a Gravel Road’ to contemporary favorites by Steve Earle ‘The Devil’s Right Hand’ and Billy Joe Shaver ‘Live Forever’ which is a nice spiritual song to new cuts from all four members. Robert Earl Keen wrote the title song ‘The Road Goes on Forever’, which tells the story of the ill-fated romantic adventures of a modern-day-Bonnie-and-Clyde duo named Sherry and Sonny. It was not a bad album, but it seems like these guys were better on their own albums and maybe this was recorded as a contract obligation, because it seems to lack the passion that they put into their previous albums. In 1975, The Allman Brothers Band released aa album titled The Road Goes On Forever.