This chapter reports on the seemingly incongruous use of 2D media-avatar drawings and 3D media-math-based digital gameplay. As part of a larger mixed methods study, we examined students´ cultural identity, player styles, and tacit perceptions of schooling while inventing their own avatars, which are analyzed as symbols representing who they are and who they wish to be as gameplayers enrolled in a yearlong game-based course. Interviews, class discussions, observations, drawings, and short questionnaires were used to analyze issues of identity that emerged during the drawing process and the ways that the pedagogical activity of making the drawings affected student engagement in the game-based learning process. An emergent typology of drawings is reported on: race-based, where the student explicitly affiliated himself with his race and cultural, and race-less avatar drawings, where the student does not associate himself with race and cultural. This typology is explained in terms of two representative students. Finally, we compare the findings with extant theories of student identity and arts-based research as well as generate implications for an integrated theory of academic, possible, and virtual selves that emphasize the dynamic and culturally responsive needs of learners in educational settings that use gameplaying as a learning modality.