On This Date: The Highwaymen’s Lead Single “Highwayman” Tops The Country Charts In 1985

A legendary song, from a legendary group.

I mean, when you put four of the biggest names in the history of country/western music together, you’re destined for greatness. And that’s exactly what we got.

Formed in 1985, The Highwaymen is country supergroup composed of Willie Nelson, Johnny Cash, Waylon Jennings, and Kris Kristofferson. Their lead single, “Highwayman” was originally written by Jimmy Webb for his 1977 album El Mirage, it was also released by Glen Campbell in 1979.

A song essentially about reincarnation, it takes you through the journeys of a highwayman, a sailor, a dam builder, and a starship pilot, and how they meet their fate, yet they’re still alive.

Inspired by a vivid, drunken dream that Jimmy had, it’s the definition of badass storytelling.

And that creativity was rewarded on this date in 1985, when the song top the Billboard Hot Country Charts, spending 20 weeks on the chart in total.

36 years ago today… and the rest is history.

And who could forget live at Nassau Coliseum in 1990.

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