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This is the selection item. If it is in your main listing of songs, it either allows or disallows a song to be copied to your iPod. It also allows/disallows it from playing in any play list. So if you have it selected/checked in a play list, it will play. If you don't have it selected, it remains as part of the play list, but will not play unless you force it to play through a double click.

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Q: What does the check mark mean on the iTunes playlist on your iPod Shuffle?
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