This thesis focuses on visual and written representations of three women of color of mixed African and European ancestry from the eighteenth- and nineteenth-century United States and Caribbean who have achieved legendary or celebrity status, even though there are only fragmentary archival sources speaking to their lived experiences. Their stories and likenesses have generated many popular or public representations since their lifetimes. The women I focus on are Rachael Pringle Polgreen, an emancipated eighteenth-century brothel owner on the island of Barbados; Marie Laveau, a free woman of color and Voodoo leader of nineteenth-century New Orleans; and Solitude, a woman who in 1802 led a revolt against Napoleon’s reimposition of slavery on the island of Guadeloupe. Each chapter focuses on one woman to analyze when, how, and by whom representations of these women have been evoked over time, and how these representations both reflect and impact the historical moments of creation and recovery. Through spatial and temporal analyses, I seek to understand how the representations’ development and movement over time have filled historical gaps, but also how they both reveal and create additional gaps in historical memory. This transnational approach examines representations of women that emerged from British, American, and French contexts. This study aids in creating broader theories about why particular figures emerge at certain historical moments, how they circulate historically and across geographical borders, and how power operates in the tension between various claims to accurately represent an historical woman, revealing new ways that ideas and knowledge about gender and race were, and are, created and circulated.