Why is music so important to us? There have been numerous attempts to answer this question, from a variety of perspectives. And yet, somehow this phenomenon that pervades so many aspects of our lives transcends attempts to capture precisely why it moves us. Contemporary philosophers and musicologists have at their disposal different and conflicting philosophies when it comes to exploring issues concerning music. In this chapter I will move beyond divergent philosophies of music, like essentialism and contextualism, and explore counterfactual perspectives on the musical experience as a distinctive form of meaning-making. Although metaphorical qualities of music have received considerable attention from philosophers, the significance of the counterfactual for the musical experience has largely been overlooked. However, by virtue of the fact that they are paradoxical configurations, metaphors provide the key to understanding counterfactual meaning-making. Based on philosophical texts and insights into how meaning is created counterfactually in our daily consciousness, I argue that, on the one hand, musical experience is counterfactually conditioned and, on the other hand, that music – through the counterfactual – contributes to meaning-making in our lives. The chapter contributes to the philosophy of music by advancing an alternative understanding of musical meaning-making through the counterfactual. By shedding new light on concepts like the irreducible and ineffable qualities of music, this understanding may also open new avenues to explore how music can be such a potent medium for understanding reality, for self-knowledge, liberation, pleasure, discipline and the exercise of power.