Song Lyric of the Day (Jimmy Webb, on the Resilience and Reincarnation of the ‘Highwayman’)

“I'll fly a starship
Across the universe divide
And when I reach the other side
I'll find a place to rest my spirit if I can
Perhaps I may become a highwayman again.”—American singer-songwriter Jimmy Webb, “Highwayman,” released on his El Mirage LP (1977)

Jimmy Webb’s song, which came to him in a dream, did not score a hit for him or good friend Glen Campbell. But its four stanzas allowed solos for mutual friends Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson, who not only used it to climb the charts but also as the inspiration for their own country supergroup, the Highwaymen.

The aging and mortality at the heart of the song now figure into the fate of the quartet who recorded it. Cash and Jennings have already passed, and earlier this month the 84-year-old Kristofferson announced his retirement, leaving Nelson—who will turn 87 two months from now—as the last man standing.

In times past, a legend like Kristofferson might have concluded his career with a lengthy, lucrative concert tour. But COVID-19 has altered these plans, like so many others.

In what form will the Highwaymen exist after death? Who knows? It’s impossible to say if either traditional forms of Heaven or Webb’s notion of reincarnation will come to pass. (It may be especially difficult for Kristofferson, who—as the blogger at “Saving Country Music” reminds us in an affectionate post-retirement tribute—has been a Rhodes Scholar, military officer, helicopter pilot, Army Ranger, songwriter, singer, and actor.)

But country music’s Highwaymen—“wild men who caught and sang the sun in flight,” to borrow Dylan Thomas’ phrase—might encounter a different afterlife given to only a few: musical immortality. Would Kristofferson ever have dreamed, for instance, that “Help Me Make It Through the Night,” “Sunday Morning Coming Down,” and “Me and Bobby McGee” would still be played?

But here they are, roughly 50 years after he recorded them, and the lyrics are also being sung by new artists. The odds are good that they will continue to be, long, long after he and Nelson “reach the other side” to join Cash and Jennings.