Book Struggle Jennings for colleges, corporate events, fairs, festivals, casinos & private shows. Contact Degy Entertainment for booking info.
Struggle Jennings writes from the place where country and hip hop overlap, a Nashville artist filed under country rap, southern hip hop, and outlaw country influenced rap. He found his mainstream audience through collaboration, first with Jelly Roll and Adam Calhoun and across the Waylon & Willie records, then held it with solo albums: The Widow's Son (2019), Troubadour of Troubled Souls (2021), and El Camino (2024). He records for Angels & Outlaws.
The name is family. He was born in Nashville in 1980 to Jennifer Eddy, daughter of Jessi Colter and Duane Eddy, and came up in the shadow of his step grandfather Waylon Jennings, immersed in the outlaw country legacy the family built.
That lineage is the frame, but the road is where the audience was won. Jennings has played rooms including Ramona Mainstage, the Orpheum Theater, and Valley Bar, drawing listeners who come for the country side and stay for the rap side. He remains a sought-after live act for fair and festival lineups, casinos, college events, and private engagements.
