I have, but only after premature disconnects, where I am prompted to scan the disk (iPod) for errors next time I try to sync. Either wrong cover art, or sometimes it looks like snow... you know the kind of static picture you used to get when TV stations would go off the air late at night?
From what I remember, as it hasn't happened in a while (changing the sync cable solved my issues), scanning the disk (first preventing iTunes from opening when the iPod is connected), then doing a normal sync ironed things out. If not, I simply deleted the CD affected, synced, added the CD back to iTunes, synced, and things appeared as normal.
That being said, it's possible you have disk errors. I would either scan your iPod with your computer, or run the iPod diagnostics and report the stats here for "turingtest2" to do a quick analysis on...