IPod Classic not syncing music playlist properly

Hi there
I've an iPod Classic that is only synching 26 out of 41 music items in my playlist. I plugged in my Nano and it synchs all 41 music item fine.
I reset my Classic but still no luck. Any ideas?
Thanks
friendl

I have reviewed numerouse forums and have tried many suggestion but still can't get my classic 80 G ipod to sync music. Everything was deleted from my ipod after synching it to my library. I only had a few podcast that needed updating. I am not sure why the ipod had the items deleted in the first place. I linked the ipod to itunes and was told I needed to reset the ipod. I reset it, loaded the newest software and still could not get the ipod to synch. I have 4335 songs and podcast total. The ipod would sync to 3775 and just stop. I have deleted itunes reinstalled. Reformatted the ipod. Reset the ipod. I have followed all suggestion and still can't get the ipod to update. Even after the ipod appears to be updated when it locks up and I disconnect it the songs do not show. Any suggestions would be so appreciated.

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    Hello justinsu15,
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    I have a 120GB black classic iPod, and I received it as a Christmas present nearly 2 years ago.
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    Hi, welcome to Apple Discussions.
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    If you have copies of all your media in your iTunes library this isn't a problem, but if you've been manually managing the content then I guess you'll want to try to recover the files from it first. See this post by Zevoneer on transferring files from the iPod to your computer. Some of the tools rely on the iPod having a healthy library which yours obviously doesn't however the manual method mentioned towards the end of the post would work.
    <hr>
    *Diagnostics Mode*
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    Reallocs: 12
    Pending Sectors: 0
    PowerOn Hours: 2202
    Start/Stops: 894
    Temp: Current 24c
    Temp: Min 10c
    Temp: Max 50c
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    1. Your drive will retain the "dirty" status until it has been successfully scanned by a disk check utility.
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    Starts/Stops: 856
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