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In the wake of the COVID-19 pandemic, there has been a notable increase in discussions surrounding the idea of hustling as an increasingly prevalent characterization of informal labor. Yet, much of this research maintains an overt focus on motivations of economic precarity and hustling as a solely economic, illicit or illegal, response to their situations. While this focus is important to understanding hustling and informal labor more generally, it overlooks the subjectivity of the hustler and their interactions with this raced, gendered, classed, and criminalized characterization of informal labor. In this paper, I examine the theorizing on hustling demonstrated by U.S. Hip Hop artists in their music, drawing on de-colonial methods to represent these artists as knowledge producers in their own right. Speaking to numerous themes unexplored in traditional hustling and informal labor research, these artist-theorists demonstrate the relationship between economic insecurity and interpersonal insecurity and demonstrate the re-articulation of this insecurity as independence. These findings raise important questions about the relationship between hustling practices and the subjectivity of the hustler, and brings questions of affect and body work to bear on informal labor practices and the raced, classed, gendered, and criminalized hustler figure.