My iPod skips certain songs- ive tried the 5 r's and i have iTunes 8

I woke up this morning and started listing to my iPod and found that it skips certain songs. about 150 (more or less) of the 500 that i have downloaded. I just dont know what's wrong with it. The songs play fine on my iTunes but as soon as I try to listen to it on my nano it skips to the next song and acts like the song doesnt excist.
I have tried the five r's, I have the most updated model of iTunes (unless im mistaken and there is an iTunes 9).
I reset all of the settings both on my ipod and on the computer- which did nothing.
I read the manuals and looked at the error reports but there is nothing that explains this at all. that I've found...
whats weird is that the songs that are being skipped were all purchased from the iTunes store. I've read a few posts about simialar occurances but nothing exactly like this. I've had my iPod for three years (if that helps)
Message was edited by: hey caseyyy

Hello,
Take a look at this link: http://forums.ilounge.com/showthread.php?t=97858 . The instruction in the last post may help you.
This other thread may also give you some good ideas: http://discussions.apple.com/thread.jspa?threadID=854344
Message was edited by: iMacPodshuffle

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