Their first album, Highwayman, was released in May of 1985 and was by far their most successful project, going to Number 1 on the US Top Country Albums Chart and was certified Platinum.
The album was produced by legend Chips Moman, who produced an insane amount of albums for an insane number of artists, playing guitar on many, along with co-writing some popular songs, including Waylon Jennings’ “Luckenbach, Texas (Back to the Basics of Love)” and Aretha Franklin’s “Do Right Woman, Do Right Man”.
“Highwayman” was originally written and recorded by Jimmy Webb in 1977 and was inspired by the life of Jonathan Wild, a London underworld figure from the 1700’s who posed publicly as a crimefighter while simultaneously running a large criminal empire.
He basically had his cronies steal some valuables, waited for the crime to be announced in the paper, then announced his group of “Thief Taking Agents” (AKA the same guys that stole it) had found the items and would return them, for a reward, to their owner. Sometimes the ring would steal from an influential person and blackmail them for favors. He also used the proceeds from this ring to bribe prison guards into letting members of his circle that got caught out of jail.
Honestly, it’s pretty ingenious. Sure, eventually he got caught and was hung publicly, but man did he have it going on for awhile.
Anyway… the song went to Number One and spent a total of 20 weeks on the charts. It was the group’s most popular song as the story connected with the lifestyles and personas of the members. In fact, it was this song that lead to their name of The Highwaymen, as their first album was originally credited to “Nelson, Jennings, Cash, Kristofferson”