This paper examines the experience and role of negative emotions in facilitating university students’ learning in world music courses. Based on a review of literature in music psychology and music education, we posit that negative emotions can engender a meaningful learning context. In this project conducted in an Australian university, we created a condition in which students were engaged in repeated listening to recordings of music from cultures different from their own, which they reported as sounding “unpleasant.” We then analysed how they overcame emotional responses through a listening exercise. The findings suggest that the students developed enhanced motivation and cognitive reflection by facing their own negative emotions through repeated listening. The article finishes with a discussion about the positive side of negative emotions and the negative side of positive emotions as they relate to music education.