Although one might not know it from the state of discussion in contemporary philosophical journals, there is a long intellectual tradition that insists on the connection between music and morality.1 Socrates' concern in book three of the Republic with permitting only certain musical modes in the ideal city is relatively well-known, but it is less noted that Aristotle ends his Politics with a discussion of musical education and the role of music making in the life of a free man.2 An abiding concern of St. Augustine and other early Christian moralists was that the music used in worship not be so sensuously pleasing as to distract worshippers' attention from the holy texts. Nor is the relevance of music to morality a strictly western preoccupation-Confucius likewise insists on the positive influence of music on human character.3 While more recent philosophers have not made much of music's connections with morality, it is an abiding theme of musical discourse. Composers, performers, critics, and listeners have always discussed music in terms. In condemning tonality, Schoenberg hinted not only that it was a spent artistic force, but also that it was somehow morally suspect.4 The music of Shostakovich was valued by Soviet listeners not just for its aesthetic achievement, but also for the way in which it was thought to reflect the dramas of life under totalitarianism. Similarly, in the music of Alfred Schnittke, Soviet listeners were said to find the metaphysical ideas and spiritual values otherwise absent from official life and culture during the years of stagnation.5 More recently, the critic Hilton Als condemned Aretha Franklin's singing style in The New Yorker, not because of the caliber of her performances, but for her manufactured, impersonal form of blackness, which allegedly ensured her popularity with whites.6 Given that musically concerned people are not likely to stop talking about music in ways that insist on or assume connections with morality, it seems reasonable to suggest that there are better and worse ways of continuing the conversation, and that attempting to bring conceptual clarity to the discussion (in those places where it might be lacking) seems a worthwhile philosophical project. In what follows, I am going to assume that music making and appreciation, as manifestations of human intentionality, are proper objects of inquiry. Listening to music is significantly different from listening to bird song, forest noises, or wind chimes.7 Some particularly thorny issues arise from this assumption. For example, in what sense is music moral? Does music have an influence on character? Is there a connection between one's aesthetic preferences and one's capacity for virtue? And if music is moral, what is the relationship between aesthetic value and worth? Is it plausible to claim that some works or performances are more or less morally worthy than others? I will not explore the implications and complications that follow from accepting music as a proper object of concern. Instead, I will attempt to make two contributions to the project of bringing conceptual clarity to the discussion of music and morality. First, I will consider the status of judgments and morally based comparisons of different musical works and genres, and offer some constraints on such judgments. Second, I will propose a Kantian analysis of moral awareness in music that I hope will help explain the enduring tendency to treat music as an object of morality. In both of these projects, I will be concerned with the status of music as experienced, and the structure of relations between musical works and listeners. So I will not specifically consider the ethical issues arising in performative interpretation, the potential character building force of musical study and performance, or problems concerning the use of music to achieve various non-musical ends.8 As an approach to my own views, I will examine the work of two philosophers-Colin Radford and Roger Scruton-who have recently considered the connections between music and morality and who make claims about particular musical works and their effects on listeners. …