This article focuses on the ways in which a select group of adolescent African American males respond to gender scripts. Drawing on interview and focus group data, the article describes four different responses to messages they receive from peers and significant adults about socio-culturally appropriate behaviors and characteristics of masculinity: 1) adapting or modifying their presentations of self, 2) internalizing ascribed gender scripts, 3) resisting, and 4) remaining conflicted about an appropriate response. Narratives highlight the complexity of gender identity development and active participation of African American boys in the construction of a masculine identity that feels most authentic, as well as the role of agents of socialization on identity.