Music wont play on my ipod, but is still shown in grey(not black) text.

I got a new 4th generation ipod a few months ago and when i tried to put music onto it 95% of the songs are unplayable by my ipod, but all of my music was working on my 2nd generation ipod and in itunes. the songs that dont work are shown in grey text and the ones that do in black. all of the artists and albums are still displayed in black even if no songs in that folder work. Every now and then when i go to sync, an error message shows up and says that one of the songs couldnt be synced and then the sync ends. and ive fully updated is and even tried reseting the ipod and redownloading itunes.

If it is a file issue, then you will need to contact iTunes Store support here.
Hope it all works out!
iMac   Mac OS X (10.4.9)  

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