How Do I Shuffle Music on My iPod?by KR Knowlin
The iPod's shuffle feature lets you randomize playback of albums, songs or even your entire music library. You may also find this feature useful if you want to listen to forgotten tracks in your library or discover songs you haven't listened to yet. Disabling the shuffle feature will return playback of a song list to its standard consecutive order. You can enable and disable the shuffle feature at any time.
Navigate to the main menu. Select "Settings."
Scroll to the "Shuffle" option. Select "Songs" or "Albums." If you select "Songs," the iPod Classic will shuffle the songs on whatever song list you listen to. If you select "Albums," the iPod Classic will play all songs of an album you select in order and then randomly select another album.
Navigate to the playlist or album to which you want to listen. Play a song to initiate the shuffle.
iPod Nano and iPod Touch
Tap the "Songs" icon on your nano home screen. If you are using an iPod Touch, open the "iPod" application.
Navigate to the song list, playlist or album you want to play.
Tap the "Shuffle" icon at the top of the list to activate the feature.