On This Day: The Highwaymen Score Lone No. 1 Single With ‘Highwayman’ in 1985

by Jim Casey

The Highwaymen—country music’s superest supergroup—scored their lone No. 1 single when “Highwayman” ascended to the top of the Billboard Hot Country Songs chart on August 17, 1985. More than 37 years after Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson joined forces, the Highwaymen’s titular tune will always be around, and around, and around, and around.

We’ll Do It Live

The Highwaymen’s first live performance took place at Willie Nelson’s annual 4th of July Picnic in 1985, where the four troubadours gathered to sing a trio of songs in Austin, Texas. Months before in December 1984, the foursome convened at Johnny’s request. “The Man in Black” was in the process of recording his new album, Rainbow. However, Cash shifted gears by putting his solo album on hold. Instead, the four legendary singer/songwriters joined forces to record 10 songs.

Among the tunes? “Highwayman,” a four-part narrative about a soul’s reincarnation that was written by Jimmy Webb. Of course, Webb, now a member of the Songwriters Hall of Fame and Nashville Songwriters Hall of Fame, was known for penning a number of hits for Glen Campbell, including “Wichita Lineman,” “Galveston,” and “By the Time I Get to Phoenix,” among others. In fact, Glen recorded “Highwayman” on his 1979 album of the same name. However, the title track was never released as a single.

Highwaymen Hit the Top

Johnny, Waylon, Kris, and Willie dropped their new album in May 1985. On Aug. 17, the album’s title track rose to No. 1 as the foursome alternated verses: highwayman (Willie), sailor (Kris), dam builder (Waylon), and starship pilot (Johnny). In September, the album reached No. 1 on the Billboard Top Country Albums chart.

And by the way, the single that Capital Records didn’t let Glen Campbell release. Well, it earned Jimmy Webb a 1985 Grammy for Best Country Song.    

The gang’s follow-up single, a cover of Guy Clark’s “Desperados Waiting for a Train,” became a Top 20 hit.

Tours followed, as did two additional albums, 1990’s Highwayman 2 and 1995’s The Road Goes On Forever. While their subsequent albums never found the same success as their original endeavor, no country supergroup—before or since—has been able to unite a group of artists as singularly acclaimed as Johnny, Kris, Willie, and Waylon.

“Four for the price of one.” That’s how Johnny Cash described the legendary creation of The Highwaymen. In our book, that’s a great deal.