IPod Classic 160 gb not playing some songs..

I got my iPod Classic last week, and everything was fine until I went to listen to the music on the iPod with my headphones not through my computer. One of my songs wouldn't start playing. So, I took the song off and re-added it back. That song started to work but then another one started doing the same thing, and it keeps doing it. Every now and then when I try to play the iPod will freeze. I plug it back into my computer and then the song works. I don't know what the problem is. Can anyone help?

I had the same problem with my iPod classic 80 GB. I spent an hour on the phone with Apple support this morning. It is interesting that I could still sync my iPhone and an older iPod, just not the Classic - so I suspected either a hardware or Mac software issue. The solution (I think) is that the permission in OS X for the device is not recognized. After restoring my iPod to factory settings, and completely deleting and reloading a new copy of iTunes, I am now able to get my Mac to recognize this iPod. Following the instructions found here:
http://docs.info.apple.com/article.html?path=Mac/10.5/en/8342.html
I was able to add permission for the "administrator" to have read and write privileges on this device. That seems to have solved the problem. Thanks to Ryan at Apple Expert for the troubleshooting. Good luck!

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