My IPod won't sync all the songs

Yes, yes. We've all heard this before. But this is different. I'll connect my Click Whell 20G iPod to my computer, and it starts syncing the songs. But then when it gets to the last couple of songs, it stops. It says "copying 499 of 500" but nothing happens. Then, when I try to eject the iPod, iTunes freezes up and I have to Force Quit. Then my iPod freezes on the "Do Not Disconnect" sign and I reset it. Then it turns back on, only to show the names of all my playlists, but no songs. No songs at all on the iPod.
iMac   Mac OS X (10.4.4)  

I beleive that your iPod got stuck during the update. Can you do a Restore and try again?
Open the iPod updater, plug your iPod with your Mac and click Restore.
If it does not work, you may need to open the disk utility, go to Tab "ERASE" and click Erase, then follow by a Restore

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