This talk comes out of a couple of current book project that attempts to theorize the relationship between blackness, art, and the cultural politics of labor throughout the 1970s and into the Great Recession of 2008. In We’re All Corner Hustlers Now, I discuss the proliferation of literary memoirs and biographical works penned by and about figures associated with rap music since the turn of the twenty-first century and especially the growing intersection between the memoirs of CEOs and musicians like Russell Simmons, 50 Cent, Jay-Z, DJ Khaled with a variety of self-help and business management genres. Focusing specifically on two works written by Curtis James “50 Cent” Jackson III, From Pieces to Weight: Once Upon a Time in Southside Queens (2005) and The 50th Law (2009), co-written with self-help guru Robert Greene, I use Jackson’s works to explore the way rappers present themselves as what Micki McGee calls the “belabored” subject par excellence. While scholars like Lester Spence and Christopher Holmes Smith have analyzed how rap music expresses this neoliberal turn, this talk argues that the literary expression of this belabored subject forces us to reconsider the legacies of Black memoir, autobiography and other modes of life writing in the twenty-first century.