iPod Problem

Anyone have an iPod? I've got a little problem with mine that I'm trying to fix. Basically I converted a CD and it shows up in iTunes and I can play it from my PC just fine. It lists the songs on the iPod but when I chose to play them it cycles through them like it only has the names of the files but no files. If I look in iTunes at the inventory of the iPod it lists the files being there, even with the correct file size.

I tried reburning the CD so I now had two copies and resync the iPod but it didn't upload the new songs. I went through the iPod as though it was an external hard drive and can't find any of those songs anywhere on there. I was figuring I might have to go into the system files for the iPod itself and delete the entries there for those files but I don't know how to open them. I tried excel and word pad for a few of the files and it was all characters that I got displayed.

I'm going to hit the Apple boards as well but thought someone here might have ran into that problem.