A system and method of generating a playlist includes searching an event database having multiple events stored therein. One of the events is identified as corresponding to a user's interest data. A song database is searched. The song database includes at least one song corresponding to the identified event. A playlist corresponding to the identified event is generated. The playlist includes a list of at least one song corresponding to the identified event and a logical link to a recording of the at least one song. Access to the playlist can then be provided to the user.