This is directed to systems and methods for ordering a playlist of media items. An existing playlist can include media sharing some characteristics, where some of the media items are unfamiliar to the user. To provide the user with a sense of the unfamiliar media items, the electronic device can order the playlist media items based on a familiarity or popularity measure. For example, the electronic device can determine the chart rankings of each media item in the playlist, and play back the media items in the order of chart ranking. This may allow a user to first listen or watch the most familiar or popular media items and get a sense for the less familiar or popular media items in the playlist.