IPod shuffle wont sync songs

My shuffle won't sync all the songs from a playlist that I created. But it will sync it from the main music list.
Why???
I never had this problem before.

The first explanation that comes to mind is that there is something different about the songs that won't sync. They might be in a format that the iPod does not support, or videos, or illegally copied DRM'd tunes, or wonky in some way.
The fact that you can successfully sync other, random, tunes suggests to me that the 'Pod and iTunes are working properly, but there is something about specific songs that is not.

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