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Although there is a scholarly and institutional assumption that imprisoned men are always hypermasculine, this performance of gender does not extend to the prison art studio. Rather than buttressing the hypermasculine traits that are rewarded on the prison yard, inmate-artists are rewarded for devotion to the art program itself. This paper examines the experiences of male inmate-artists through interviews with formerly incarcerated artists and prison art program staff. Respondents consider the art studio to be a “safe” space, a sanctuary within a dangerous environment. In the studio, men are allowed, and even encouraged, to explore themselves emotionally to become true artists. They also regularly socialize across racial lines, sharing supplies and offering encouragement. The men generally agree that they should protect the art program, thereby safeguarding a “freer culture” that does not exist elsewhere in the prison. My findings support those that argue that prison art programs are beneficial for individual inmates, the prison institution, and broader society, but adds an important mechanism for how this is accomplished: these art programs allow inmates to drop the hypermasculine imperative. This has implications for the study of gender and organizations more broadly speaking – just as Ely and Meyerson (2010) found on oil rigs, getting individuals in masculine (and dangerous) workplaces to find a new focus allows them to cast aside the rigid guidelines that formerly shaped their gendered behavior. Creating “alternative spaces” in heavily gendered organizations can reduce members’ necessity to enact this gendered behavior, thereby “undoing” gender.