A system and method of generating a playlist of affinity related media files using affinity relationship data. In one aspect the relationship affinity data is based upon a user rating score obtained from a population of user's ratings associated with media file attributes. In one aspect, a media file attribute which can include an artist, album, title, and genre information associated with a media file is received from a user, indicating the user's desire to create an affinity playlist of media files having an affinity relationship based upon the selected media file attribute.