With a special performance from Merle Haggard, Kris Kristofferson, Willie Nelson and Blake Shelton slated for the Grammy Awards on Sunday night (Jan. 26), let’s look back at another Grammy-connected collaboration involving Kristofferson and Nelson.
“Highwayman,” sung by the Highwaymen (a supergroup featuring Johnny Cash, Waylon Jennings, Kristofferson and Nelson), won the Grammy in 1985 for best country song. Written by Jimmy Webb, it reached No. 1 on Billboard’s country songs chart the same year.
Once you get past the dated ‘80s sound effects, it’s a unique classic. The song doesn’t even include a chorus.
Each of the four singers takes a verse as a troubled soul being reincarnated through history. First comes Nelson as a stagecoach robber in the Old West, then Kristofferson as a sailor on the high seas, then Jennings as a worker on Hoover Dam and finally Cash as a starship pilot.
In its video, as each verse (and life) ends, another rider on horseback joins a mysterious posse galloping through a desert afterlife. The upcoming Grammy performance may not recreate the iconic lineup, but all things considered, it does feel like a spiritual descendent of the original project.
Enjoy the Highwaymen’s classic music video, “Highwayman.”