Q: I’m wondering how I can set a particular playlist to ‘shuffle’ so when I listen to it on my iPod classic it will shuffle the songs rather than always playing them in the same order. Is there a setting I need to change on my iTunes or iPod?
A: There is no way to make an individual playlist shuffle differently each time you play it. You can set the playlist to shuffled in iTunes, but this will simply provide a shuffled order that remains static on the iPod.
You can, however, enable shuffle globally on the iPod. This will shuffle the playback of any music you select while shuffle is enabled, including playlists, artists, albums, genres, etc. The Shuffle setting can be found on the iPod classic under the “Settings” menu and can be set to either Off, Songs or Albums. The Songs option will shuffle all tracks within the current selection, while the Albums setting will sequentially play all of the selected tracks within each album and then randomly pick the next album.
The Shuffle options can also be accessed during playback simply by pressing the center SELECT button on the iPod until the shuffle options screen appears. The click wheel is then used to choose from the three shuffle options which can be selected by pressing the center SELECT button again.