Critics of commercial rap music in the United States maintain that rap artists face pressure from major record labels to sell records. As a result, rappers infuse their music with hypermasculine, homophobic, and misogynistic lyrics. However, underground rappers, individuals not signed with large record companies, are supposedly free of such burdens, possessing the ability to say whatever they want. This work explores this claim. What do underground rappers discuss in their music? Is it different from mainstream artists? Specifically, I analyze 237 songs of underground White and non-White male rappers from 2006 to 2010. Performing a content analysis, I found that White artists relied heavily on the tropes of hypermasculinity and misogyny in their music. They made fewer references to racially political and social themes (e.g., racial profiling, police brutality, and racist policies) than non-White artists, what I term racial evasion. Rappers of color also included hegemonic subjects (i.e., violence, hypermasculinity, and misogynous references), but to a lesser degree than Whites. Surprisingly, there are lower percentages of homophobic lyrics for each group. These findings reveal that both White and minority male underground performers produce similar music to commercial artists, but rappers of color inject their songs with more racial and political themes. In this case study, I detail my theoretical approaches and describe the concerns generating a sample for a population that is not readily accessible via standard music outlets (i.e., Billboard Magazine). Additionally, I detail the complications that occur performing a content analysis of rap lyrics.