Nashville rapper Struggle Jennings reps a city not exactly known for its gang violence, so the level of brutality unleashed in his new video “Black Curtains” may come as a bit of a surprise. When considering family tradition, however, it may not—Jennings is the grandson of late country music legend Waylon Jennings, one of the notorious godfathers of the rough and raw “outlaw country” genre.

Jennings—who has been rapping for the better part of a decade—is currently in prison on drug trafficking charges. While the “Black Curtains” video was just released and the full I Am Struggle album dropped in May, fellow Southerner Yelawolf did a guest verse back in 2011 for the album’s first single, “Outlaw Shit.” Struggle was out on bond when the “Outlaw Shit” video was shot, and it was released just days before Tennessee authorities arrested him again—on charges that “Free Struggle” proponents say were based on wire-tapped phone calls that merely mentioned narcotics, but do not constitute grounds for his charges.

The new “Black Curtains” video has drawn a healthy amount of attention, namely because it contains footage of Struggle inside the Davidson County, Tennessee jail where he has been held since 2011. Authorities from the Davidson County Sheriff’s Office (DSCO) say Struggle’s team “duped” them into believing that the crew would be filming a documentary, not a music video. A statement on Struggle’s blog says otherwise: “Our plan all along was to film enough footage to release a short film, in music video format, to build awareness and excitement for the full-length I Am Struggle documentary.”

In another post, Struggle says that when the DSCO gave permission to film, the reason he was “sitting here in jail” started to make sense. “It was the only way to make my words so real that they’d change my life. That they could change someone else’s life. My Grandma Jessi always warned me not to put my kids out there in the media. But I wrote ‘Black Curtains’ for my son, Will. Even though the message is the same for all the sons of the struggle, I’m speaking straight to him.”

A true family affair, Struggle’s son Will stars in the video, and the song centers on a sample of Struggle’s grandparents (Jessi Colter and Waylon Jennings) singing “White Room.” As Struggle explains on his blog, “Everyone in that video means something to me. Every place, every word has meaning. So when the curtains are pulled back, you’re gonna see a piece of my soul. Whether you think I’m right or wrong, all I ask is that you listen to my story. And try to see the truth in it.”  —Katie Moore (@kmoorenyc)