Because of the disproportionate number of violent males in American society (particularly in the juvenile justice system), teachers and researchers should afford greater scrutiny to the relationship between masculinity and violence. Incarcerated male youth have unique issues not only because of their incarceration, but also because of their gender. Through an examination of masculinity in a social context, this paper considers issues that are common to young men in correctional facilities. In order to better serve male youth, teachers and researchers in correctional facilities should better understand concerns particular to male students. Specifically, these concerns include the intersections of masculinity and violence, the social networks that positively and negatively affect young men, identity construction, emotional expression, and literacy in the lives of male youth. In addition to theoretical analyses of masculinity and its affects on incarcerated youth, this paper offers practical applications for teachers working with young men.