It’s been twenty-five years since country’s first supergroup, the Highwaymen— Waylon Jennings, Willie Nelson, Johnny Cash, and Kris Kristofferson—joined forces to record. These four giants shared a deep and complicated friendship through the years as the leaders of Outlaw Country, and had cut duets in every combination, but they’d never made a record as a foursome until 1985 with Jimmy Webb’s “Highwayman,” a song which fit their collective persona and provided enough verses for each to take one. The result: a #1 single and album on the Billboard country charts. Two more albums followed, Highwayman 2 (1990) and The Road Goes On Forever (1995).
The Essential Highwaymen gathers 38 solos and duets recorded between 1970 and 2008, plus seven of their quartet performances. It includes some fine covers of Kristofferson’s songs and plenty of choices among straightforward country, lush orchestrations, and “boom chicka boom” to keep fans of their individual styles happy. A previously unreleased track is the quartet’s version of “Desperadoes Waiting For A Train,” recorded live at Farm Aid in 1993. The collection closes with a spare and elegiac yet uplifting rendition of “Live Forever,” with the four singing harmony together.