A portable media player (12) communicates with a host computer (22) for enabling a user of the player to manage media distribution using the control software of the host computer (22). The host computer (22) can send a GUI that is displayed on the otherwise "dumb" player (12), and the user can view the GUI and press a single button to command the control software to download a media title to the player (12). The host computer (22) can periodically poll the player (12) to determine its status.