"Struggle Jennings Top Radio" brings together the raw grit and authenticity of country rap and southern rock, featuring standout tracks by Struggle Jennings himself alongside an eclectic mix of artists. Kicking off with "Outlaw Shit" featuring Waylon Jennings and Yelawolf, the playlist sets a rebellious tone that's echoed in Willie Nelson's live rendition of "On The Road Again" with The Avett Brothers. Struggle Jennings appears multiple times, notably in collaborations like "Me And My House" with Brantley Gilbert and "Behind Bars" with Jelly Roll.

This playlist also dives into the melancholic sounds of John Moreland's "You Don't Care for Me Enough to Cry" and the introspective "In Color" by Jamey Johnson. "Monte Carlo" and "Black Ribbons" showcase Struggle Jennings' storytelling prowess, while tracks like "Ballin" by Logic and "Sour Grapes" by John Prine add diverse flavors. Whether you're here for the modern outlaw spirit or rugged lyrical depth, this playlist has something to keep your speakers bumping.