Over the past decade art educators have engaged in a dialogue about a reconceptualization of art education theory and practice. This reconceptualization has roots in cultural studies, anthropology, and critical theory. One focus has been on the notion of art as visual culture. This article is organized into four sections. The first section looks at the notion of representation and racialized looking. The second provides a discussion of Black identity and the process of signifying and reifying stereotypes of African Americans in American popular culture. Next, the article focuses on the film "Bamboozled" and finally, connections are provided between theory and practice as a means for examining racial difference and stereotypes.