This chapter looks at youth work and music production as practices through which to work alongside and support young men, specifically towards doing critical gender work around masculinities with young men at risk of violence. The chapter shows the ways youth work and music production allow relationships and trust to be built and the ways this can open up spaces of critical reflection around identities, emotional life and relationships with violence for young men. To do this it draws on ethnographic research conducted in London, UK during a period in which I was also a youth worker. The context is a central government funded intervention programme to ‘end gang violence’ where I was employed as a key worker to several young men who identified with peer groups that were being surveilled by the police as active street gangs.