iPod classic 160GB won't play certain songs iTunes plays fine

Hi, I've got a really strange problem with my iPod classic. There are some songs (strangely, usually ones by "Glee Cast") that my iPod classic absolutely refuses to play at all. It will usually attempt to play the first second or so of the song, and then skip to the next song in the playlist. All of the songs that do this also don't show any album artwork on the iPod (even though they do have the artwork showing in iTunes). Also, all of the songs that refuse to play on the iPod work perfectly fine using any audio program on my MacBook Pro running Lion. I've tried them with iTunes, VLC, Quicktime, and even Quick Look. I've also tried restoring the iPod (multiple times), and when I resync back my ~25GB library, it's still the same exact songs that have the same problems.

Does anyone know why my iPod would not play a handful of very specific songs that work perfectly fine on my computer (showing the files aren't corrupted), and why it's always those exact songs? And if so, how do I fix it?