School choirs have been stigmatised for adolescent males in New Zealand, resulting in constraints in involvement, bullying, and threat to gender identity. In other national contexts, boys who sing in choirs have experienced a negative stereotype associated with accusations of inferior masculinity, yet little research has probed whether such forces are at play for their New Zealand counterparts. The current study was conducted with a sample of adolescent male school choir members in New Zealand (a country where essentialist gender attitudes have existed). Adolescent male choristers' perceptions of the gender stereotype, its moderation by cultural context, and how the stigmatised choral domain was negotiated, were explored within a framework of critical masculinities. Such a stereotype and wider implications for gendered structures found in society at large were confirmed. Personal and school-based factors enabling the male choristers' endurance in a domain that rendered their construction of masculinity subordinate, are discussed.