Background/Context: Ladson-Billings's concept of Culturally Relevant Pedagogy for African American children has been widely reinterpreted in various contexts for racialized students. In this reflective essay, I consider its challenges in Canadian contexts. Focus: I use my early ethnographic work to illustrate important aspects of culturally relevant pedagogies, to raise cross-cultural differences, and as a springboard to engage with newer theorizations. Research Design: These studies took place in a majority Black K-5 school; in addition, I conducted two studies in Illinois. I argue that the goals of culturally relevant education for Black students within the formal mechanisms of Canadian schooling are impeded by the official policy of multiculturalism that frames the Canadian imaginary and does not include Black people. Conclusions/Recommendations: In the quest for pedagogies relevant to students' lives, I call for fuller conceptualizations of Blackness that complicate notions of culture, transnational relationships, and global migrations. Lastly, I call for teachers to embrace the nexus of issues that students negotiate in their daily lives as part of any potentially transformative pedagogy.