A media organizer and entertainment center includes an importer for importing individual media/data selections and automatically assigning each selection at least one associated category flag pursuant to predetermined or user defined criteria. The center also includes a storage device for storing compressed data corresponding to the plurality of individual media/data selections and the associated category flags and a retriever for retrieving selections from the storage device based upon user selection of one or more of the associated category flags, and a data decompresser that translates the compressed data into playable digital or audio media data. With the center, playable digital or audio media data can be advantageously transported, organized, played or recorded through or on a variety of products or devices.