Music tends to be highly repetitive, both in terms of musical structure and in terms of listening behavior, yet little is known about how engagement changes with repeated exposure. Here we postulate that engagement with music affects the inter-subject correlation of brain responses during listening. We predict that repeated exposure to music will affect engagement and thus inter-subject correlation. Across repeated exposures to instrumental music, inter-subject correlation decreased for music written in a familiar style. Participants with formal musical training showed more inter-subject correlation, and sustained it across exposures to music in an unfamiliar style. this distinguishes music from other domains, where repetition has consistently been shown to decrease inter-subject correlation. Overall, the study suggests that listener engagement tends to decrease across repeated exposures of familiar music, but that unfamiliar musical styles can sustain an audience’s interest, in particular in individuals with some musical training. Future work needs to validate the link proposed here between music engagement and inter-subject correlation of brain responses during listening.