This article focusses primarily on the findings relating to the musical participation of boys in one Melbourne school. As part of a project that investigated boys' attitudes and participation at fifty-one schools, several contextual features were identified that set "Balton Boys" High School' apart from other participating schools, allowing this school to achieve a breadth of male musical involvement, thus challenging long-observed, frequently documented gender stereotypes. This research contributes to an understanding of factors which encourage boys to participate broadly, promoting insight into "permissions" granted to boys in the context of specific school cultures. It highlights the propensity for some school contexts to reinforce and perpetuate stereotypical gendered behaviour, and for others to interrupt and challenge stereotypes, effectively promoting a breadth of musical participation amongst middle-school boys. (Contains 2 notes.)