Coercion and violence over body and soul were not the only mechanisms deployed at the dawn of the Cuban slaveholding plantation system to extract obedience and subjugation from uprooted African captives. In their efforts to pedagogically incite some sort of “willingness” to submit, Cuban masters also engaged theatrical performances and the visual arts. In this talk we will examine some examples of these artistic forms and the unintended, and rather paradoxical, effects they had over the lives of slaves.