Rapper Struggle Jennings is a Nashville-born performer whose music draws inspiration from both his grandfather’s (country legend Waylon Jennings) outlaw sound, and modern hip-hop, rock, and country traditions. A cohort of Yelawolf, Jennings first grabbed the public’s attention with his 2013 debut I Am Struggle. He found mainstream success via collaborations with Jelly Roll and Adam Calhoun and solo efforts like The Widow’s Son (2019) and Troubadour of Troubled Souls (2021).
Born Will Harness, the musician adopted the moniker “Struggle Jennings” when he started rapping. Jennings’ early tracks were often based around samples of his grandfather’s songs juxtaposed with eerie hip-hop beats as a backdrop for his intense and street-minded rhymes. While starting his career and forming ties with other hip-hop figures such as Yelawolf, Harness came up on drug-related charges and went to jail in 2011. While incarcerated, his focus on his music sharpened deeply. During the course of a five-year sentence, Struggle saw the release of his 2013 debut album, I Am Struggle, and also had video footage taken in jail that resulted in a video for his single “Black Curtains,” as well as a documentary that told his strange and twisting story. Shortly after being released from prison in early 2016, he released the Return of the Outlaw EP. He then collaborated with rapper Jelly Roll on three connected albums released in 2017 and 2018: Waylon & Willie, Waylon & Willie 2, and Waylon & Willie 3. The studio album, The Widow’s Son, arrived on Angels & Outlaws in 2019 and included guest spots by Bubba Sparxxx, Jeremy Penick, Yelawolf, and others. Jennings teamed up with fellow country/hip-hop crooner Adam Calhoun for 2020’s Legend EP, followed by the fourth volume of Waylon & Willie. In 2021 he released his third solo effort, Troubadour of Troubled Souls, with another Adam Calhoun collab, Outlaw Shxt, arriving later that year.