Systems and methods are provided for on-the-fly playlist shuffling. There can be multiple ways to perform the shuffling. In one instance, the electronic device can organize a new playlist by sorting the media files based on a parameter. In another instance, the electronic device can organize a new playlist by shuffling the media files. In yet another instance, the electronic device can first sort the media files into groups of media files based on a parameter. The electronic device can then shuffle the media files within each group. In this manner, the media files can be randomized but only within each group. In all instances, the current media file can continue to play without any interruption. Finally, the electronic device can sort the media files based on the context of the media file that is currently playing.