In the current Swedish society differences are growing regarding who has the right to learn and use artistic forms of expression. Where a citizen comes from, socially and geographically, more and more determines her tools for handling life. A variety of steering documents state that all Swedish youths should have the right to learn and use artistic forms of expression. At the same time the demands on equal assessment and grading are growing stronger in Sweden, which force teachers to put efforts on documentation and grading, instead of musical learning. The aim of this article is to present and discuss possibilities for pupils to develop Cultural Citizenship through music in the school situation where different views of equality are competing. This article discusses to what extent it is possible to conduct democratic inclusive music education towards Cultural Citizenship in the current time of increased demands of documentation, assessment and grading. To come close to the phenomena of Cultural Citizenship in music educational settings, and to offer theoretical tools for understanding and reflection, the to some extent contradictory political and educational philosophies of Hannah Arendt was used. The philosophical exploration implies a need of teachers’ authority and responsibility when it comes to an agreed upon view of the musical world, and ways to organize meetings with that world in inclusive ways in schools towards a functional Cultural Citizenship.