This article explores the characteristics of Nairobi underground hip hop that fit under a common theme of what I term as the music’s “political seriousness,” which is the common notion that the music must be substantive, thought-provoking, socially critical, and never vacuous. This political seriousness is composed of four characteristics: Mau Mau gendered legacies, political love, a reliance on neoliberalism, and a critique of the state. Hip hop’s goal is to make a political space that both proves its worth and remedies Kenya’s flawed polity. This is an imperfect endeavor, as its dependence on late capitalism, normative gender constructions, and conventional understandings of the Mau Mau war contribute to rap’s troubling tendencies. Nonetheless, these artists regard hip hop as authentic or real music because it advocates for the economically disenfranchised, contributes to Kenyan social commentary, and participates in an imagined global hip hop culture.