Struggle Jennings’ Redemption Story From Prison To Double Platinum Artist, Finding His Purpose
Struggle Jennings "Off The Porch" Interview
We recently sat down with Nashville artist Struggle Jennings for an exclusive “Off The Porch” interview! During our conversation he talked about his upbringing in Nashville, his dad getting killed when Struggle was 10 years old, reveals what lead him down the path of selling drugs, getting arrested when he was 14, going to live with his uncle who taught him the importance of hard work when he was 15, going to prison for the first time when he was 20, getting sentenced to 13 years in prison when he was 30, his music career taking off while he was locked up, shooting a music video in the county jail, making the decision to turn his life around when he went to prison, his children being put in foster care while he was away, getting custody of them when he came home, being home for 10 years now, explains how he met Jelly Roll while they were both pushing their music, reveals why he has never signed with a major label despite numerous offers, upcoming documentary, being on parole for 9 years, fans telling him that his music helped change or saved their lives, finding his purpose, reveals he felt like giving up on music numerous times, being one of the first ones to combine country & rap together, people telling him that it wouldn’t work, the creative process for creating his breakthrough song “Outlaw Sh*t” with Yelawolf, the song recently going double platinum, getting his flowers for helping start the country rap genre, giving a testimony after all of his shows, upcoming tour & album that starts in March, his new EP ‘Young Struggle’ with Street Flavor, reveals he plans to drop 5 albums this year, what to expect on his upcoming country album, challenging himself to do country music, getting into acting, being in his first movie ‘Day Of Reckoning’, being in the upcoming movie ‘High Stakes Holiday’, plans for 2026, Waylon Jennings new posthumous album, and much more!
Struggle Jennings
https://www.instagram.com/iamstruggle/
Interview by Haze
https://www.instagram.com/mike_tall
DGB Media
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"Off The Porch" Interviews Playlist:
https://www.youtube.com/playlist?list=PLGZpaFw4cQ6PLtV-w_-9To6I7yrhShcGr
"Off The Porch" is Dirty Glove Bastard's exclusive interview series where artists, producers, DJs & industry insiders are given a platform to tell their unfiltered story. Dirty Glove Bastard was created in 2007 to shine more light on the buzzing, regional music scenes in the South & Midwest.
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Channel Owner•3,188 views•Jan 20, 2026
