Critiques of anachronism have been used to dismiss art made in the Caribbean since the arrival of Christopher Columbus. This article argues that in order to render Caribbean art in the critical imagination, one must first decolonize notions of time foundational to the discipline of art history. Through a series of portraits of black subjects produced in Haiti during the nineteenth century, it sets aside temporally bound notions of innovation and avant-garde aesthetics that center art history and considers the manner in which these portraits defused the authority of Western frames of looking. The portraits demonstrate how postrevolutionary Haitians appropriated the seemingly hegemonic aesthetic codes of Western art in ways ambivalent to, if not wholly detached from, their temporal-bound values of origins, the singular or original work of art, and the linear concept of formal innovation. Instead, these portraits are works generated and thus rendered within a different value system, where the copy and the ability of a work of art to be reproduced across time was prized far more than a singular, original, individually authored object, and where the literal work of art superseded its materiality and form and in every sense transcended linear time.