Some songs on playlist grayed out on iPod

Feb 9, 2015
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I have an iPod touch with software version 8.1.3 that has a 56.6 GB capacity and 9.3 GB of empty space. I have a playlist that copies from my Mac Pro partially, but the remaining songs on the playlist are grayed out and therefore won't play. Those same songs will copy to my iPhone. I have tried to delete the grayed-out songs to start over, but can't get them to delete (whereas I can delete songs in black from my iPod). I have tried re-starting my Mac and re-doing the sync several times, and the same thing happens. Any ideas how to get these songs onto my iPod?

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