This article examines perceptions of language by two African American teenage males who travel between the intricacies of Black English and Academic English in their daily lives. To understand youth language perceptions, the article is guided by the following inquiry: Given the historically dichotomous relationship between Black English and Academic English, how do youth perceive language in their struggle to acquire academic success? In this examination, the author argue that classrooms should be more responsive to students’ languages and identities.