Between the years of 1997 and 1999, Nelson, Kristofferson, Cash, and Jennings also provided the voice and dramatization for the Louis L'Amour Collection, a four CD box set of seven Louis L'Amour stories published by the HighBridge Company, although the four were not credited as "The Highwaymen" in this work.
Besides the four formal members of the group, only one recording vocal artist ever appeared on a Highwaymen recording: Johnny Rodriguez, who provided a Spanish vocal on 'Deportee', a Woody Guthrie cover, from "Highwayman".
Formed in 1985, the group did not have an official name when they released their first album on Columbia Records. The album, entitled Highwayman, was credited to "Nelson, Jennings, Cash, Kristofferson". The single "Highwayman", a Jimmy Webb cover, became a #1 country hit. Their cover of Guy Clark's "Desperados Waiting for a Train" reached the Top 20. (Clark is frequently referred to as "The Fifth Highwayman".) The album was produced by Chips Moman.
In 1990, the group reunited for a second effort, titled Highwayman 2, which reached #4 on the country album chart. The Lee Clayton-penned song "Silver Stallion" was the first single and made the country Top 40. The album was nominated for a Grammy for Best Country Vocal Collaboration. Highwayman 2 was produced, once again, by Moman. Six of the songs were written or co-written by members of the group.
The group's final release prior to Jennings's death in 2002 was the 1995 Don Was-produced album The Road Goes on Forever, (a Robert Earl Keen cover), with the single, "It Is What It Is". The four singers then returned to their solo careers. A tenth-anniversary edition of The Road Goes on Forever appeared in 2005, with several bonus tracks added as well as, in some versions, a DVD containing the music video for "It Is What It Is" and a documentary entitled Live Forever – In the Studio with the Highwaymen.