Struggle Jennings is the step-grandson of country legend Waylon Jennings and nephew of Shooter Jennings, but carries the family’s country music tradition in a different way. 

Destined to be an outlaw, his music is deeply rooted in country but presented as the basis for powerful rap songs instead of the family’s traditional country. 

The self-described black sheep gravitated toward hip-hop at a young age and enjoyed some local success in his home town of Nashville, but it took a trip to prison to give him the focus he needed to finally figure out the direction he need to go. 

A frequent collaborator with longtime friends Yelawolf and Jelly Roll, Jennings has gone through a complete transformation, releasing several charting hip-hop albums since 2016, the year he emerged from prison as a new man and decided to turn his life into something positive. His music has now become a source of inspiration for fans as Jennings shares a message of stability and healing that comes from the heart and from the many lessons he learned while working through his personal demons. 

Late last year, Jennings and Jelly Roll released their fourth collaboration, Waylon & Willie IV, an homage to his Waylon Jennings and Willie Nelson, while simultaneously showcasing how far Jennings had come in a short five-year period. 

Ensuring the family music tradition will continue on indefinitely, Jennings’ daughter, Brianna Harness, will open the show on May 13 at the Rockstar Lounge, along with up-and-coming country rapper Nuke Bushner.