This study explored the young, marginalised masculinities of 25 boys awaiting trial for various offences in Cape Town, South Africa. The boys came from impoverished areas created by Apartheid legislation and most of the boys were involved in gangs. Through their language and descriptions of practices the boys construct three intersecting discourses of masculinity, as they strive to be the toughest gangster, the sweet “mommy’s boy” and a “gentleman” who provides and protects for his family. Although the boys end up in the criminal justice system awaiting trial, they still have a certain amount of agency, as they slide between discourses and temporarily become gangster superheroes. These boys’ masculinities are bound up with their context: they live in a place with a violent past and a tumultuous post-Apartheid present, precipitating substantially ambivalent subjectivities.