Despite its modest size and its subject’s demeanor placed among and against a plethora of imposing works surrounding it in the Louvre, Marie Benoist’s Portrait d’une négresse is a deceptively straightforward portrait that is, in fact, historically, culturally, and visually complex. It is powerful in its engagement with a variety of themes relevant to its time of creation (the beginning of the nineteenth century) and now. Such concerns include, but are not limited to, the coalescing dynamics of race, gender, class, exoticism, science, nationhood, agency, modernity, and the circuitry of actual and implied male and female gazes across time and space. Using the portrait as a historical, cultural, aesthetic, and ideological point of departure, this chapter will consider ways in which Black women in visual representation constitute ideological tropes of modernity that necessarily include contradictory markers of denigration and empowerment. By extension, this chapter will also contemplate “negress” as a significant term and concept relevant to the past and present and probe its aesthetic and ideological implications for the cultural history of Black women in visual culture.