Date: 2008-08-06 02:36 pm (UTC)
In a program the size of iTunes, there's no reason why it can't do this.

Of COURSE there is! Apple's designers didn't think you might want to do that, so it's impossible!

(You can get close: Create a smart playlist, that live updates, where the criteria is "play count = 0". Play that playlist on shuffle. When it runs out, edit the criteria to be "play count =1". Repeat)
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