An example method includes maintaining (i) a scheduled playlist of media items for playback by one or more playback devices, (ii) a current playback position within the scheduled playlist, and (iii) a priority media item having a playback length. The method also includes receiving, from a playback device, a request to play back the scheduled playlist and, based on the received request, transmitting the priority media item to the playback device for playback beginning at a first time. The method also includes determining a next media item from the scheduled playlist based on the current playback position within the scheduled playlist at a second time that follows the first time by at least the playback length of the priority media item and, beginning with the next media item, transmitting one or more media items from the scheduled playlist to the playback device for playback after the priority media item.