The encounter – and sometimes confrontation – of music with various cultural backgrounds challenges many preconceptions and prejudices on music making and learning. The rise of what is now often called ‘world music’ has not only brought new sound worlds to Western ears, but digs deep into existing systems of belief. In discussing both Western classical and world music, concepts such as tradition, authenticity and context are often used with firm conviction. On closer examination, however, they are applied with ambiguous or even contradictory meaning. A cross-cultural exploration of these concepts reveals that they are not nearly as clear, stable and value-free as they may appear. A more dynamic interpretation of these terms is needed to understand contemporary realities of music making and education at all levels, and to enable teachers to apply these concepts to everyday studio and classroom practices.