A service that provides playback of media content, that may include advertising content, to a user. The system comprises device, that may be a portable wireless device, where the wireless device has a media drive and an application that reads content from a medium inserted in the media drive. The system further comprises a service that communicates with the wireless device via a wireless network. The service provides control commands to the application program for controlling playback of content from the medium when inserted in the media drive. The service may also provide advertising content to the user based on a user profile. A fee may be paid for the delivery of the content and/or the advertising to the user.