This article explores the responses of three New York hip-hop entrepreneurs—Russell Simmons of Def Jam, Shawn Carter (Jay Z), and Curtis Jackson (50 Cent)—to the Occupy Wall Street mobilization of 2011. Occupy protested against extreme levels of inequality, declaring that it represented the 99 percent in opposition to the 1 percent financial elite. While these moguls were all within the 1 percent ranks, seen by many as emblematic of winner-takes-all neoliberal realignment, they had nonetheless built star brands that represented people, in intersectional race/class terms, at the other end of the economic spectrum. This tension was negotiated in markedly different ways by the three moguls. Through these comparative cases, this article engages and assesses scholarly accounts of race, popular culture, and neoliberalism. It suggests that certain dominant frames do not leave much room to draw distinctions between the moguls’ responses and that this may be politically concerning.