Abstract Music enjoyment and familiarity are closely related but often confounded in studies of neural music processing. Here, we investigated their distinct contributions to cortical oscillatory activity and neural tracking of music using electroencephalography (EEG). Thirty-two participants listened to self-selected all-time favourite songs, recent favourite songs, and tempo-matched songs from disliked genres. This novel paradigm dissociated familiarity from enjoyment by including highly enjoyed songs that differed in familiarity. Spectral power and cortical tracking (using Mutual Information) were analysed using linear mixed-effects models with enjoyment and familiarity ratings. Familiarity was associated with increased left-frontal alpha power, whereas enjoyment predicted increased theta and beta power, demonstrating distinct oscillatory signatures for these dimensions. An interaction revealed that the positive relationship between enjoyment and theta power was strongest for highly familiar music. Cortical tracking analyses showed that greater enjoyment was associated with reduced delta-band tracking, with a significant interaction indicating that this negative relationship was present for highly familiar songs but not for less familiar songs. These findings indicate that enjoyment and familiarity differentially shape neural responses to music and highlight the importance of modelling both factors to disentangle their distinct effects on neural activity during music listening.