An intelligent synchronization tool ensures access to desired content in a
manner that automatically keeps the content current on the portable media
device. A variation threshold or user-specified degree of content
variation may be introduced among content downloaded to a user's mobile
device to prevent the user from becoming bored. Furthermore, intelligent
synchronization may automatically populate the portable media device with
popular content to save a user time and/or use passive monitoring
techniques to ascertain a user's preferences for subsequent population.