This article explores the idea that teachers, even when aiming to implement culturally and personally relevant pedagogies, are subject to passing on colonial agendas and practices that stultify learning in art classrooms. I argue that even in self-governing, majority non-European societies, well-intentioned teachers can unintentionally perpetuate colonial educational agendas that narrow students' learning, as well as the ideas students deduce about art, culture, and their roles in contributing to them. I focus on Jamaican and Anglo-Caribbean art classrooms, where many teachers and students have non-European lineages and a shared national heritage rooted in slavery and colonialism. I conclude the article by raising implications for how art educators there and elsewhere might avoid unconsciously engaging in neocolonial pedagogies, especially when teaching non-White students whose heritages are rooted in colonial oppression.