A system and method for providing previews of media files from a user's media collection to an associated portable media player are provided. In general, media files from the user's media collection are selected based on a play history of the user and optionally a user profile of the user. Once the media files are selected, previews of the media files are generated. The previews may then be transferred to the portable media player during a docking, or synchronization, process. Thereafter, the previews may be played by the portable media player and, if desired, selected by the user for transfer to the portable media player. The media files corresponding to the selected previews are then transferred to the portable media player during a subsequent synchronization process.