Johnny Cash and Waylon Jennings’ Grandsons Partner for Rendition of ‘Highwayman’

by Clayton Edwards
(Photo by Jim Smeal/Ron Galella Collection via Getty Images)

Some things tend to be hereditary, in one way or another. Several people who sing or play an instrument will tell you that they come from a musical family. However, some pedigrees are a little more impressive than others. This is the case for Whey Jennings and Thomas Gabriel. Whey is the grandson of Waylon Jennings and Jessi Colter. Thomas is the eldest grandson of Johnny Cash. Both men spent time with their grandparents when they were young.  Whether it is in the blood or just in the influence, these fellas picked up a thing or two along the way.

Whey Jennings and Thomas Gabriel both have budding musical careers. Jennings has an EP and a live album out now. Likewise, Gabriel has an EP and a studio album. Recently, the two teamed up to pay tribute to Waylon Jennings and Johnny Cash. The pair took one of the biggest songs that their famous forebears recorded together and gave their own rendition. Check it out below.

If you didn’t know that those were the grandsons of Johnny Cash and Waylon Jennings it would still be a good cover of “Highwayman.” Both singers have voices that fit the tune like a glove. Additionally, the electric guitar work on the cover is rock-solid. However, knowing who these two are makes this song hit a little differently.

Whey Jennings takes the vocal parts for Waylon, Kris, and Willie. Then, for the final verse, Thomas Gabriel steps in to cover Johnny Cash’s part. That’s where the energy of the video changes. It’s not just Gabriel’s gravelly voice. It’s how the two men throw their arms around one another. More than that, it’s in the emotion you can see written on their faces as they sing together.

It’s an amazing celebration of two late great Outlaw legends. Johnny and Waylon would be proud of these guys.

Johnny Cash and the Gang Come Together

Whey and Thomas’ ancestral bond brought them together for the song. It just made sense for them to cover “Highwayman.” In a way, that echos the beginnings of The Highwaymen.

Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson were all friends before they were bandmates. In 1984, Cash was in Switzerland shooting a Christmas special. He invited the other three icons out to join him.

While there, they played together on stage and behind the scenes. The personal and musical chemistry was obviously present. So, it just made sense to put a band together.

The Highwaymen played together for a decade. During that time, they cut three albums and toured the globe.

Like Thomas Gabriel and Whey Jennings, Johnny Cash and the Highwaymen came together over a love of music and a common bond.