In this article, I consider the artistic and cultural impacts of Western-style art instruction in Yoruba schools. I discuss the trajectory of Western influence on Yoruba educational institutions, beginning with early Christian missionary activities in Yorubaland through the periods of colonization and postcolonial emendation of Nigeria's national education policy. The influence of Nigeria's pioneering modernist artist, Aina Onabolu, on the art curriculum of Yoruba schools is discussed in relation to the ideology that traditional artistic practices must be replaced with modernist art methods for progress. Conversely, some Indigenous Yoruba artists developed transitional practices that evolved beyond the limitations of both Onabolu's modernist viewpoint and established traditional methods, as exemplified by the dynamic art of Yemi Bisiri. The essence of this transitional artistic paradigm is further clarified through attribution to the philosophical construct of transmodernism. I conclude with a consideration of transmodernism as an ideal philosophy for guiding Yoruba artistic practices.