IPOD ONLY SYNCING CERTAIN PURCHASED MUSIC!!!

So, my iPod will only sync certain purchased songs. Is this weird?
Out of all my purchased songs my iPod will only sync about 1/4 of them. All of my songs were purchased & downloaded within the same day... so their should be no difference in the ones that are syncing and the ones that aren't. Right?
PLEASE I NEED HELP!

Try playing one of the affected songs for a few seconds in iTunes.
Do you get asked to authorise? If so, and if you do, do the songs transfer next time you sync?

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