80GB Classic will no longer sync with Outlook

I have a 80GB Classic that will no longer sync my Outlook contacts or calender. It will sync everything else, music, movies, games, but than it just hangs. It will say that it is syncing and not to disconnect, but it will stay that way for hours and not do anything. I also have a 64GB touch that sync with the same library and the touch sync just fine. Does anybody have any ideals or suggestions?
Thanks!

Found out that my iPod was hanging on the photos not Outlook. Deleted the iPod Cashe and problem is sloved.

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