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iTunes will not shuffle a playlist at all. I have tried deleting it and making a new playlist and it still will not shuffle. Yet, if I make a completely different playlist with different artists that playlist will shuffle. What can I do to make it shuffle?

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Would you mind stating what you have tried? – Josiah Oct 13 '12 at 18:53
    
Does it not shuffle visible in the list (without playing) or does it play sequentially even if shuffle is enabled? – patrix Oct 14 '12 at 10:28

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