This study examines the philosophical question of how it is possible to appreciate music aesthetically as an expressive art form. First it examines a number of general theories that seek to make sense of expressiveness as a characteristic of music that can be considered relevant to our aesthetic appreciation of the latter. These include accounts that focus on resemblances between music and human behaviour or human feelings, on music's powers of emotional arousal, and on various ways in which music may be imaginatively construed by listeners. It argues that none of these are entirely satisfactory. Then it proposes an alternative account, focusing on what is involved when our appreciation of music as an expressive art is informed by our awareness of it as something that is expressively interpreted in performance. It is claimed that this offers the basis for a better understanding of at least some aspects of expressiveness in music and its relevance to aesthetic appreciation.