Hi, certain tunes aren't playing on my iPod now - they are iTunes tunes

Hi,
I have iTunes set so I manage iPod tunes manually. Certain tunes aren't working on my iPod - yet they are working on iTunes. They are all songs I bought on iTunes.
I will select the tune on the iPod, hit play - and the iPod after a sec. will skip to the next song. Do I have to re-drag these tunes from iTunes and delete the ones on my iPod?
Thanks.

Have you tried setting it to Automatic loading? If so does it still happen?
Perhaps they were corrupted when you loaded them? eg - disconnected iPod while still loading or a power outage.
Try restoring your iPod and then try updating your iPod afresh.
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