Drawing from a six-month ethnographic study, this article explores the negotiation of gendered identities through classroom literacy practices in an urban high school, paying particular attention to how gendered identities are interwoven with those of race, class, and other social identities during literary discussions. I draw upon the notion that identity is multifaceted, shaped through language, and deeply context-dependent to show how students were able to hold multiple, gendered subject positions--like debater, athlete, and smart student--simultaneously. At the same time, however, the gendered identity work that students engaged in through textual and oral discourse was constrained by the other subject positions they held outside of class and by the people with whom they were interacting. Findings suggest that educators must recognize that literacy learning, as a form of interpersonal communication, is not only an academic endeavor but also a negotiation of social identities and thus a social practice that can delimit or offer new possibilities for students' self images and life choices.