The Untold Truth Of The Highwaymen

To back up a little bit, it wasn't Stuart's idea that Cash, Nelson, Jennings, and Kristofferson form the Highwaymen, but he was an early cheerleader. 

According to the Willie Nelson and Friends Museum, the idea for the four men to collaborate came in 1984 when Cash enlisted the three musicians to play on his Johnny Cash Christmas TV special that was filmed in Switzerland. Back at the hotel, they got to jamming and hanging out and realized it would be fun to team up and try something new. 

But there was a little something else. According to Classic Country Music, Cash had been bummed around that time because his newer music wasn't doing as well as it did in earlier years. Stuart, who was Cash's son-in-law at the time, said Cash got his "first glimmer of hope" while in Switzerland playing with Jennings, Nelson, and Kristofferson.  

But with four distinct singing voices, specifically between Cash and Nelson, harmonizing proved difficult at first. Stuart said he got the idea for the quartet to cover "Highwayman." 

He brought it to Cash and said, "Listen, four verses, four guys, no harmony required."

Cash liked it, as long as he could sing the verse about the starship, Stuart recalled. The friends recorded "Highwayman," and it went on to be the supergroups only No.1 single. The song also won a Grammy Award in 1985 for Best Country Song, per AllMusic.

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