In Touré’s 2012 book, Who's Afraid of Post-Blackness?: What It Means to Be Black Now, Touré quotes Henry Louis Gates, stating, “if there are 40 million black Americans, then there are 40 million ways to be black.” While there exist as many ways to be black as black Americans, and while American pop culture and mainstream media are experiencing new exposure to different modalities of blackness, the rhetoric of black authenticity and the perceived need to prove oneself based on a racial category are still prevalent. Through a close reading of excerpts from Stew’s play Passing Strange, Colson Whitehead’s novel Sag Harbor, and Paul Beatty’s novel White Boy Shuffle, I will use the analytics of authenticity and blackness in literature to explore how identity manifests itself for black males in hip hop music. In focusing on rappers Childish Gambino and Kanye West, I complicate a static popular image of blackness that is transformed through different modes of socio-economic status and education level by these artists. My research explores the lingering rhetoric of authenticity, focusing on contemporary intersectionalities of identity in regards to gender, socio-economic status, and race. These intersectionalities can conflict and influence one another for individuals who struggle to personally define themselves, while simultaneously being defined by their communities. In focusing on how black identity is created within the arts, specifically literature and music, my research aims to unpack the idea of “authenticity” surrounding blackness and make meaning of the ways in which black male teenagers and young adults explore, qualify, and define their identity in regards to race. Ultimately, my analysis sheds light on a more heterogeneous representation of black identity, while suggesting that restrictions on identity for black Americans are not obsolete in the 21st Century.