The Highwaymen - Biography
By Jonny Whiteside
The Highwaymen – Johnny Cash, Waylon Jennings, Willie Nelson and Kris Kristofferson – were easily country music's all-time greatest supergroup. Like a flesh and blood Mount Rushmore, the powerful quartet brought together some of the most progressive, talented and famed artists in the idiom's history. An unprecedented phenom, the act proved highly successful at first. Their unlikely origin lay with a single song written by Jimmy Webb, the pop alchemist behind hits songs like "Wichita Lineman" and "MacArthur Park." The song that sparked this group effort , Webb’s "Highwayman," was among his most unusual, a reincarnation-themed saga of four separate lives common to a single man (Webb said he wrote the song after waking from a wild dream where he was an 18th century highwayman being "chased within an inch of my life by these grenadiers on horseback"). The songwriter brought it to Glen Campbell, who had enjoyed tremendous success with Webb's work in the late 1960s. Campbell recorded the song as title track for his own Highwayman album (1979 Capitol) but the disc was not among Campbell's more successful. Later Webb pitched the song to Jennings, who politely passed. Neither Cash, nor Jennings, nor Nelson nor Kristofferson had entertained the notion of joining forces but after country singer Marty Stuart (who was also Cash's former son-in-law) suggested it would make it a novel collaboration with great commercial potential and Campbell urged them to cut it, the four decided in 1984 to give it a try.
One could not hope to assemble a more formidable country music dream team.
Cash first broke out of Memphis's rockabilly epicenter, Sun Records, in the 1950s with hits like "Walk the Line" and "Folsom Prison Blues." He subsequently produced an extraordinarily ambitious and creative series of long players after moving to Columbia Records in 1958 where he pioneered the "concept album" and dealt in socio-political subject matter any other country singer would have considered anathema. By 1968, with Live at Folsom Prison and "Boy Named Sue," he was outselling the Beatles. Jennings, the brilliant, black leather-clad Texas singer-guitarist had kick-started the Outlaw Movement in the 1970s with Wanted: the Outlaws (1977 RCA), the very first Nashville-produced album to sell over a million copies. Jennings and Cash had been close friends since the two shared a house together in the mid-1960s. Nelson, the Outlaw movement’s shaman, was a veteran singer-songwriter who’d first burst on the country scene as writer of classic early 1960s hits like Patsy Cline's "Crazy" and Faron Young's "Hello, Walls." He subsequently parlayed his offbeat, idiosyncratic vocal style into superstardom. Kristofferson, the renegade Rhodes scholar who had chucked everything to take a maintenance job at a Nashville studio in order to pitch his songs to Cash, had seen the gamble pay off when Cash recorded his "Sunday Morning Coming Down" and quickly rose to become one of the most respected writers and performers among a new breed of Nashville cats. The four enjoyed a long-running, mutual skein of alliance and truth be told, both Cash’s and Jennings’s careers had cooled quite a bit by the mid-1980s while Kristofferson's acting career seemed to be eclipsing his musical activity.
Things got hot almost as soon as the album Highwayman (1985 Columbia) was released in May 1985, produced by veteran studio wizard Chips Moman. The title track quickly went to number one on the Billboard Hot Country chart and hung around the upper reaches for the next four and half months. With its strong radio airplay and record sales, it closed out as the number five country song of that year and also won Webb the Grammy for Best Country Song of the Year. 1985 was a pivotal moment in country music history – while George Strait had re-invigorated interest in classic country, the world had yet to hear from Randy Travis, Dwight Yoakam or Garth Brooks. The Highwayman allowed each of its members a chance to reassert their primacy as the field's top dogs. A follow up single, the band's version of Guy Clark's "Desperados Waiting for a Train," made the number fifteen spot and they played to capacity crowds wherever they appeared. It seemed an auspicious start – the album was soon certified Platinum – but the solo career demands of each necessarily precluded any of them from immediately concentrating on a second album.
By the time of Highwayman II (1990 Columbia Records), much had changed. Garth Brooks was the new 800 pound gorilla in modern country, Cash had been ignominiously dropped by Columbia several years earlier, Waylon had gotten sober (and to many country insiders had lost his guts), while Kristofferson was more popularly associated with action flicks than artful songcraft. But each remained an instantly recognizable and bankable commodity and the album sold respectably, reaching number four on Billboard's Country Albums chart. It was certified Gold and earned them a Grammy nomination for Best Country Vocal Collaboration, but the first single, "Silver Stallion," only made 25 on the country chart. Their last effort, The Road Goes on Forever (1995 Liberty) was a dud, despite the fact that Johnny Cash was enjoying a critically acclaimed career at Def American. But producer Don Was (who had recently tanked Jennings' career with the disastrous Waymore's Blues) was seemingly unable to capture the chemistry which Moman exploited to such advantage on the previous releases and the set existed mostly as an object of curiosity. By the time Capitol (Liberty's parent company) re-released a bonus track-enhanced version of The Road Goes on Forever in 2005, Jennings was dead and Cash's health was rapidly failing, while Nelson and Kristofferson soldiered on with all their skills intact. But when the Highwaymen nailed it, as on their first album, they really got the job done and it's doubtful that any of its members regretted for one moment taking on this unusual and memorable project.
