Abstract: Disclosed are various embodiments of systems and methods for generating composite mediasets from mediasets, each comprising media items, associated with a plurality of users. In some embodiments, individual and/or group recommendations are provided for creating a group playlist by aggregating user taste data for a plurality of users in a group. In other embodiments, systems and methods are provided which allow for sharing and playing of a group playlist by users in a group, each of which has a media playback device. In still other embodiments, systems and methods are provided for dynamically building a composite playlist that may be updated as users enter and/or leave the group. One example of an interactive entertainment application also is described for use at a venue to entertain live guests with music selections that are dynamically influenced by the guests' individual tastes.