Since 2010, Washington, D.C. has undergone major shifts in its racial demographics and property value. What was once a city that boasted a seventy percent population of black residents in the 1970s, giving it the moniker “Chocolate City,” has become an urban landscape overrun by developers, construction sites, and new residents who assist in branding the “new” Washington. What does that branding include? Not only new buildings, but an investment in an aesthetics that makes use of “Chocolate City’s” past to define its new and “authentically urban” future. I argue that despite the intentional attempt at erasure of black life and culture from the capital’s landscape, native black Washingtonians continue to produce an aesthetic birthed out of the Chocolate City of the 1970s, but decidedly invested in the contemporary focus on specificity of place. To that end, “Washington, D.C., a Black Aesthetic, & the Politics of Renewal” is an excavation of literary, film and visual artistic production as a means by which to interrogate what I identify as a new practice in black aestheticism. I articulate that black aesthetic, which I term an aesthetics of loss, as existing alongside and despite ongoing displacement and dispossession of black people and black spaces, and I enact a multi-methodological approach to get at its nuance. My work centers around black cultural curators in Washington, D.C. who use literature, film, music, and visual art to inscribe themselves and their communities as in place in the face of systemic erasure. To be clear, by “in place” I mean taking up material place, not just ideological space, on the mapping of the District of Columbia. Ultimately, this dissertation asks: What does it mean to live when you have been pronounced dead?