Off The Record Live: Struggle Jennings Talks Rap Roots, Grandpa Waylon, ‘Troubadour of Troubled Souls’ and More

Videos by American Songwriter

Videos by American Songwriter

“The first concert I ever went to was, of course, my grandpa Waylon,” Struggle Jennings said on a recent episode of American Songwriter’s Twitch show, Off The Record Live.

The grandson of the great outlaw country legend, Struggle Jennings began his own musical journey in a very different way—raised by his mother (who refused any “handouts” from his famous grandpa), he found his voice in rap and began making his own tapes when he was still a kid.

“Rap music is what spoke to me—what we were going through, what my friends were going through, what I was going through—so I automatically gravitated towards that,” Jennings said. “As young as I can remember, I was standing in the mirror rapping. I started writing my own raps—back then, you’d get a single and it would come with the instrumental. So, I would just freestyle to it. God knows where they’re at, but there are hundreds of little tapes out there where I’d hit ‘Play’ on one tape player and ‘Record’ on another.”

From there, Jennings’ creative arc began—after a few encounters with the law, he got serious about his craft and began forging a career that’s earned him a legion of devoted followers (you can read more about his rise in this story HERE). With frequent collaborators like Jelly Roll, Adam Calhoun, Yelawolf, and more, he’s released a plethora of albums and racked up millions of streams.

Sitting down for Off The Record Live, Jennings also spoke about his most recent record, Troubadour of Troubled Souls, which candidly speaks to the struggles he’s faced in his life, as well as the forces of evil that influence society on a mass scale. Performing his hit song “God Come Back Home” alongside its co-writer, Caitlynne Curtis (who’s a phenomenal artist in her own right), the room was illuminated with the passionate energy of his music.

Watch the full interview and performance below:

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