All reflective music educators ponder the questions posed by this title. Over the years, they have channelled an enormous amount of energy into the improvement of musical teaching and learning in our schools. Ross (1995) argues that these efforts continue to be futile, for the basis of thought and practice is misconceived. This paper examines Ross's thesis highlighting and developing its existential component. A case study illustrates the argument for placing authentic self-expression and ‘music proper’ within the context of wider contemporary debate.