Despite its popularity, hip-hop has remained one of the most woefully underexamined topics within criminal justice and criminology. Given the reality that hip-hop music represents lyrical expressions from criminal justice’s most overrepresented population; the aforementioned paucity is all the more perplexing. Utilizing a latent and manifest content analysis of a random sample of 200 hip-hop songs, drawn from platinum-selling albums between the years 2000 and 2010, the current study examined the manner and extent to which hip-hop artist’s portrayed the criminal justice system. The results demonstrated that law enforcement was the branch of the criminal justice system most likely to be mentioned by hip-hop artists (58.27% of mentionings) followed by corrections (33.81%) and courts (7.91%). Subthemes that emerged from hip-hop discussions of law enforcement and corrections are also discussed. Unfairness and powerlessness inductively emerged as the two general themes from the hip-hop criminal justice portrayals and are discussed within a procedural justice framework. Suggestions for future research and policy implications are put forth.