A system and method for enabling a user to request and download selected media files from distributed content provider sites via the Internet. The system includes a plurality of user sites each including a player/receiver housed in an enclosure having a simple user interface, a plurality of content provider sites, and a transaction server site. The player/receiver enables the user to connect to the transaction server via the Internet to access a program guide listing available media files. The user is then able to select a desired file and, via the player/receiver and Internet, request the transaction server to authorize download of the selected file. The file request along with file encryption and transfer instructions are sent from the transaction server via the Internet to the content provider site storing the requested file. Requested files are then dynamically encrypted by the content provider site and securely downloaded to the requesting player/receiver. The requesting player/receiver is uniquely capable of decrypting a downloaded file concurrent with playing back the file on a conventional home television set and/or audio system.