A growing literature is now claiming that participation in the arts, and music in particular, is beneficial to health. Whilst some claims are made for music benefiting physiological health, the main benefit would seem to be for gains in emotional wellbeing. There is a gender dimension to participation in music, with girls being more likely to participate, and boys who wish to sing or play certain instruments facing the disapproval of a “macho” peer culture. The paper reports on qualitative research carried out into the views of 18 boy singers in a well-known church choir in England, using observation, diary keeping, individual and group interviews. The boys showed a deep appreciation of and engagement with the music. They exhibited many features of high personal wellbeing, including the social competence to circumscribe the proscriptions of “macho” culture. Those from state schools were very critical of the superficial way singing was tackled in their schools. Secondary schools were reported as being more accepting of their singing than primary schools. All the boys were academic high achievers and were particularly keen on autonomous reading, again being critical of the guided reading offered by their schools. The paper concludes that state schools could do more to involve young people, including boys, in singing, and to take the subject more seriously, but acknowledges that the pressures on state schools to deliver literacy and numeracy are making this difficult.