Itunes will not update all music onto my ipod

I'm using 5th Gen iPod w/ latest software and itunes with latest software (as of 8/5/09)
I had to restore my ipod the other day, so it began the process of copying all my music library back to my ipod. it attempted to copy a certain song for about 10 seconds, then stopped and indicated that the sync was complete. In reality, it did not copy that song, and it stopped there. I changed my ipod settings so that it would only copy checked songs. I unchecked the particular song, and tried again. It copied another 100 songs or so, but then stopped on another. These songs play fine on my computer, so i don't believe they are corrupted.
Does anyone have any ideas on why this is, and what i can do to fix it?

Just try this on that one song first....the first one it stopped on.
Take it out of the itunes library list. If it asks about putting it in the recycle bin, say NO.
Then add it back into the itunes library. Will it sync now?

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