Utilizing a mixed methods approach using quantitative content analysis and rhetorical criticism, I examine Issa Rae's web series The Mis-Adventures of Awkward Black Girl and its presence online as a performance of unruliness. The themes of satire, awkwardness, and platform inform my analysis of the series and the conversations that surround it. After a review of the historical, mediated representations of race in the U.S., I argue that Rae navigates constraints on her voice through Crunk Feminism and as an unruly woman. She offers indirect critique of oppressive structures through satire and the performance of awkwardness. Online platforms, like YouTube, contribute to her capability to enact this critique. To this end, I examine not only Rae's performances in ABG, but also I conduct quantitative content analysis of ABG's YouTube comments. In this analysis, I focus on expressions of identity, representation, and community. Ultimately, I posit the satirical wielding of awkwardness as a unique educational tactic, which creates space to interrogate stereotypical representations of Black womanhood.