Music-evoked pleasantness has been extensively reported to be modulated by familiarity. Nevertheless, while the brain temporal dynamics underlying the process of giving value to music are beginning to be understood, little is known about how familiarity might modulate the oscillatory activity associated with music-evoked pleasantness. The goal of the present experiment was to study the influence of familiarity in the relation between theta phase synchronization and music-evoked pleasantness. EEG was recorded from 22 healthy participants while they were listening to both familiar and unfamiliar music and rating the experienced degree of evoked pleasantness. By exploring interactions, we found that right fronto-temporal theta synchronization was positively associated with music-evoked pleasantness when listening to unfamiliar music. On the contrary, inter-hemispheric temporo-parietal theta synchronization was positively associated with music-evoked pleasantness when listening to familiar music. These results shed some light on the possible oscillatory mechanisms underlying fronto-temporal and temporo-parietal connectivity and their relationship with music-evoked pleasantness and familiarity.