On This Day in 1985, a Group of Outlaw Country Legends Hit No. 1 With the Story of a Soul’s Journey Through Time

On this day (August 17) in 1985, the Highwaymen were at No. 1 with “Highwayman.” The song spent a week at the top of the chart and won a Grammy Award for Best Country Song, which went to songwriter Jimmy Webb. Later, the group took their name from the track. Interestingly, one of the group’s members had passed on it years earlier.

Johnny Cash, Kris Kristofferson, Waylon Jennings, and Willie Nelson released their first collaborative album, Highwayman, in 1985. At the time, they didn’t have an official name for the group. Instead, the album is credited to “Nelson, Jennings, Cash, Kristofferson.” The same was true for their 1990 sophomore release, Highwayman 2. They finally took the Highwaymen name in 1995 with their third LP, The Road Goes on Forever.

Webb brought the song to Jennings a few years earlier. However, he wasn’t interested in recording it. He had already heard Glen Campbell’s version of the song and didn’t think it would suit him. Later, Campbell played the song for Cash. It wasn’t until Marty Stuart played the song for the four of them together that it clicked. It was the perfect fit. There are four verses, four incarnations of the soul, and four members of the group.

Jimmy Webb Wrote the Highwaymen’s Signature Tune After a Vivid Dream

Jimmy Webb wrote “Highwayman” and recorded the original version in 1977. The song came to him after a dream that felt like it could have been a memory from a past life.

“I had an old brace of pistols on my belt, and I was riding, hell-bent for leather, down these country roads, with sweat pouring off of my body,” Webb recalled. “I was terrified because I was being pursued by police, who were on the verge of shooting me. It was very real,” he added. “I sat up in bed, sweating through my pajamas. Without thinking about it, I stumbled out of bed to the piano and started playing ‘Highwayman.’ Within a couple of hours, I had the first verse.”

[RELATED: On This Day in 1976, Johnny Cash and Waylon Jennings Recorded a Pre-Highwaymen Hit for the Ages]

After finishing the first verse, Webb decided that the song’s titular character didn’t truly die. Instead, reincarnation allowed his soul to live on into the distant future.

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