Struggle Jennings Talks Jelly Roll, Waylon, and Keeping It Authentic 

Country rap artist Struggle Jennings has a pedigree unlike anyone in Nashville, or anywhere else for that matter. Being a trendsetter and a rebel seem to be in his blood as the grandson of guitar legend Duane Eddy and country singer Jessi Colter, the step-grandson of the late country icon Waylon Jennings, and the nephew of artist/producer Shooter Jennings.

Working closely with his longtime friend Jelly Roll, as well as with artists like country singer Julie Roberts, rapper Bubba Sparxxx, and chart-topping rap rocker Yelawolf, Jennings’ popularity is soaring among listeners who ordinarily wouldn’t have been interested in either country or rap. His #1 Billboard Rap Digital Songs single with Caitlynne Curtis, “God We Need You Now,” and the Jelly Roll duet “Hard to Hate” from Jennings’ upcoming album Monte Carlo, have appealed to a whole new generation of music lovers.

“We been doin’ this a long time, me and Jelly Roll started together,” Jennings said by phone from a truck pulled over somewhere along a Tennessee highway. “We started about at the bottom as you can get, selling CDs on the side of the road, out of our trunk, printing CDs up in my living room, putting labels on ‘em ourself, recording in my bedroom in a closet. And we’ve been independent the entire time.”

Jennings’ music doesn’t fit the mold of today’s commercial country, but his success digitally makes country radio and the big labels practically irrelevant. “Our message has always been a little too rough around the edges for the mainstream regardless of how much momentum we got,” he said. “Labels like to be able to control an artist, tell them what kind of music to make, how to dress, they like to have a say in it. We’ve been kind of out of the box. When I started blending country and rap I was one of the first to do it and it wasn’t accepted, it was something that even people close to me thought wouldn’t fly. Because we’ve lived really crazy lives, in and out of jail and poverty and dealt with a lot of addiction, our story and our songs and us pouring our heart out into the music wasn’t always really radio format. They never let us in the front door, but Jelly found a way to get in the back.”

“I’m an ‘80s baby,” he continued, “so I grew up on listening to a lot of Tupac, UGK, I was big into Master P. I’m from the South so it was a lot of the Southern rappers. But I had the backdrop of Waylon being my grandfather, and getting an opportunity and the blessing to be able to go backstage and see some of the shows when I was little, and to know him as the man that he was. He was always larger than life to me. He was more like a father because my dad was murdered when I was 10.”

Jennings’ primary sales exposure is bound to be via the internet for the time being, but once radio and the label heads figure out what they’re missing they may begin to sing a different tune. But given his growing DIY success, Jennings may well never need them for anything. “I think there’s been a big shift in the radio stations and the labels realizing that the consumer wants authenticity,” he said. “The consumer needs something real to hold onto these days.”   

Monte Carlo is set to be released in May. You can follow Jennings at

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