A system and method for distributing playable content and for recommending playable content to a user where the recommendations are generated at a wide area network content server considering information extracted from one or more playback devices of the user by means of an intelligent agent resident on a processing device. The intelligent agent functions to scan the memory devices associated with the processing device and/or other devices in communication with the processing device for the purpose of determining what playable content is resident on the memory devices so scanned. Data related to the playable content uncovered during a scan is uploaded to the wide area network content server where the data is usable by a recommendation engine to make more informed recommendations for that user.