This dissertation addresses the works of art of two free men of color, Vicente Escobar (1762-1834) and José Antonio Aponte (date of birth unknown-1812), who lived in late eighteenth and early nineteenth-century Havana. I offer the first consideration of these two artists together in order to illuminate the scope of visual artistic practice of free people of color prior to the foundation of the fine arts academy, the Academia de San Alejandro, in 1818. Creole and Spanish elites who supported the foundation of the school expressed concern that blacks had been "dominating" the arts and excluded them from studying there.