Shuffling playback content based on multiple criteria

Each of one or more songs in a song list is analyzed to determine whether the song satisfies a set of criteria at its current location. For each of the one or more songs that satisfies the set of criteria, the song is kept at its current location in the song list. For each of the one or more songs that does not satisfy the set of criteria, an attempt is made to select (e.g., randomly) another song in an unprocessed portion of the song list that satisfies the set of criteria. If a selected song satisfies the set of criteria then the song and the selected song are swapped. However, if greater than a threshold number of attempts to select a song that satisfies the set of criteria are made, then the song is kept at its current location in the song list.