Written by Jimmy Webb in the late seventies, and later recorded by Glen Campbell, Highwayman only really emerged in the mid eighties (sort of like the reincarnating highwayman in the song) under the singing of Cash, Jennings, Kristofferson and Nelson together - who later called their quartet The Highwaymen.
The ballad in their hands received the right touch and treatment; they manned it up. Not lingering so much over the construction of the song like Campbell, they made it sweeping. With background synth and on-the-road beat, and with the themes (not necessarily having to be interpreted as pantheistic reincarnation) of generational life defying death, of human entrepreneurial progress, of continuing on through catastrophe, the song is so quintessentially eighties that it sounds now, at least to me, like an anthem specifically for the eighties; the anthem of the eighties - or at least one of them.
The Highwaymen went until 95, and here they are in a Long Island concert in 1990; and the eighties are still there, like that outlaw - though it’s the nineties.