A system and method for transferring album art from a client computer to a portable media device (PMD). A graphical user-interface allows a user to select a track for transfer to the PMD. A media player application (MPA) verifies that the PMD is capable and authorized to receive album art. The MPA queries the PMD for an album object storing album art for the selected track. If an album object corresponding to the selected track exists, a reference to the selected track is added to the existing album object. If an album object corresponding to the selected track does not exist, the MPA transfers a new album object referencing the selected track and storing album art for the selected track to the PMD. The MPA further connects to a web site authorized to sell an audio CD associated with a track when a buy flag is detected on the PMD.