Since the 2009 Ontario Ministry’s Equity and Inclusive Education strategy called for the implementation of culturally responsive pedagogy across the board, the voice of the Black creative and content in arts curriculum remains invisible. This primary research centers on the perspectives of African, Caribbean, and Black artists called on for the first time to discuss the successes and challenges of teaching culturally responsive arts in diverse Ontario classrooms. This qualitative study uses critical race theory to examine their experiences of working in Greater Toronto schools and surrounding areas in Ontario, Canada. Using cultural arts from across the African diaspora as a tool, their artistic work is situated within culturally relevant pedagogy, which is an alternative approach to centering on identity, cultural frames of reference, and critical student learning. Yet, as these Black Canadian artists garner successful impacts from culturally responsive teaching in classroom space, they identify simultaneous challenges of institutional unpreparedness, anti-Black racism, cultural appropriation, and legitimizing their cultural artistry to school administration. Semi-structured interviews include rich narratives from artists specializing in contemporary and traditional expressions of orality, visual arts, dance, and drumming/percussion from the African diaspora. While navigating instances of unbelonging, recommendations are proposed to improve the understanding of the artists’ role and improve Canadian educational institutions’ relationship with Black creatives in inclusive education.