You can set iTunes to play songs, albums, or groupings (collections of the movements of a classical work) in random order.
Here are ways to shuffle songs:
To turn shuffle on or off, click the Shuffle button (shuffle is on when the arrows are blue):
To choose whether iTunes shuffles by songs, albums, or groupings, choose ControlsÂ > ShuffleÂ > [Option].
If you select â€œby Albumsâ€ or â€œby Groupings,â€ iTunes plays the songs in the order in which they appear on the album or in the grouping, and then chooses another album or grouping at random.
When shuffle is on, you can’t drag songs into a new order in a playlist.