A system and method, operable by a processor running on a computing device and stored on a tangible computer readable medium, the system and method creating continuous, fixed duration, fixed size, or other such playlists for use on an individual listener's portable music player, as a programming guide for an Internet radio station, or the like. Information can be drawn from a number of recommendation sources to help generate such playlists based on a dictionary of terms. Recommendation sources are sources available via the internet or other published information that identify the order in which songs are presented or played, and which may be aggregated and processed into song sequence data that allows the instant system and method to utilize the experience, effort and musical expertise of others to generate a continuous playlist. Exemplary recommendation sources include, but are not limited to, published Disc Jockey (“DJ”) playlists, radio (terrestrial, satellite or internet) station websites from which playlists can be extracted or derived, individual listener playlists, or the like.