Songfacts®:

• Gangstagrass banjo player and vocalist Dan Whitener wrote this song about issues that bluegrass and hip-hop have in common. With both genres being "folk" music in the sense that they arise out of working class, underclass, and sometimes outlaw cultures, Whitener believes they have much more in common than what may initially appear.
  
  "I was thinking of something that affects everybody equally but also in very different ways," Whitner told Songfacts. "So I thought about prison. I tell people it's about recidivism and it's about how if you go to prison and you get out, statistically you're very likely to find yourself back in prison again. Why is that? I certainly don't have an answer, but it's our role as musicians and songwriters to observe something and ask why.
  
  Beyond that, I was thinking about people get into all kinds of prisons, in their own minds and in their own lives. I think, depression and the feeling of hopelessness, are powerful important things to me, and I really want to try to give voice to that."
• Though Whitener wrote the base of the song, including most of the lyrics, the Gangstagrass MCs R-SON and Dolio the Sleuth brought their own verses.