My dissertation explores the challenges of representing African American freedom during the era of gradual emancipation in the nineteenth-century United States. Art and cultural historians have previously looked to commemorative monuments and abolitionist propaganda to examine the impact of emancipation on the visual arts. As a result, the symbolic depiction of emancipation has received greater scholarly attention than the visible signs of freedom constituted by the labor, dress, and setting of daily African American life. Such signs, my project argues, appear most legibly in antebellum portraiture—a format that stands apart from the generalizing impulse of most depictions of free Black life and enables the rare pictorial expression of individual narratives and experiences.Across three chapters, I analyze portraits painted by white artists Charles Willson Peale (1741-1827), Thomas Waterman Wood (1823-1903), and William Sidney Mount (1807-1868), whose work attends to the ways in which free people of African descent publicly presented aspects of their identity in the antebellum North and Upper South. I place these portraits in close dialogue with a broader visual culture of urban views, genre scenes, and theatrical ephemera that indelibly shaped the way freedom looked and the way portrait subjects could be rendered or understood. Investigating topics including the portrait’s evolving conventions, sites of display, and painting’s materiality, I consider the ways in which Black subjects expose the limits of painted portraiture as a mode of representation in the early and mid-nineteenth century. This study contributes to a growing body of scholarship that positions visual art as a vital force in the struggle for emancipation, and it draws painting into conversations happening across the study of nineteenth-century photography, print media, reception studies, and the history of abolition from which the medium has been largely excluded.