This article examines how stereotypes operate in the social construction of African Canadian males as ‘at risk’ students. Cultural analysis and critical race theory are used to explain how the stereotypes of the youth as immigrant, fatherless, troublemaker, athlete, and underachiever contribute to their racialization and marginalization that in turn structure their learning processes, social opportunities, life chances, and educational outcomes. The article concludes by suggesting that addressing the stereotypes is not only a task for educators but also for society as a whole.