Playing songs repeatedly or randomly

iTunes can repeatedly play a single song or playlist, or play songs in random order.

Use the buttons at the bottom-left corner of the iTunes window to shuffle or repeat a playlist. When you turn on Shuffle mode, songs are played in random order. You can't change the order of a playlist when Shuffle is on.

For more information, choose Show Balloons from the Help menu, then point to a button. (Mac OS 9 only.)