This essay analyzes how the presence of Francisco Oller’s monumental painting, The Wake, challenged the narrative of progress set forth in the Exposición de Puerto Rico de 1893 (Fair of Puerto Rico). The fair celebrated four hundred years of Spanish rule over Puerto Rico and emphasized the cultural and economic advancements achieved throughout that time. As a contrast to the many displays of the island’s bounty, The Wake offered a vision of jíbaros (Puerto Rican peasants) celebrating a baquiné, an Afro-Caribbean tradition honoring a deceased child. The painting brought attention to the poverty and marginalization of the peasantry as well as their persistent practice of nonnormative rituals. Oller, like many of the other social-reform-minded intellectuals of Puerto Rico, focused on the jíbaro class in order to critique their lifestyles but also to propel social transformation that could improve peasants’ quality of life. My study intervenes in the scholarly literature of Oller and the politics of the fair to show how The Wake visually asserted the prejudices and deterministic preconceptions about these peasants that characterized the views of late-nineteenth century sociologists. More importantly, however, careful observation of the painting reveals subtle inaccuracies such as the scarcity of food and drink in the scene, errors that conflict with the conclusions intellectuals of the time were drawing about the peasantry. These ambiguous compositional choices disclose an unbridgeable gap between the critique The Wake offered and the fair’s objectives, but they are also central to the painting’s relevance in Puerto Rican culture today.