I've got a 160 GB iPod Video (or "Classic" as they call it now). I've noticed that there are some songs that don't show up. These songs are definitely in my iTunes. And when I look at the contents of my iPod through iTunes, it shows the songs are there. But when I look for them on the iPod itself, it doesn't show the artist listed. I'm really drawing a blank on this one.
1. Make sure the Compilations option is turned off. 2. If it is (and it probably is) then it is bug. There is no firmware update for this that I know of. The fix is this. Put everything that is missing in a playlist. It is fine to jumble everything together. Make sure to click on that playlist in your iTunes "Your iPod" (under the music tab) to allow it to be sync'd up. Once you do this, your iPod will be able to find those songs by artist.
I think your ipod data base might be corrupted or have bad sectors. That's why some of your songs don't show up. you can check it with a tool called Doctor to see what kind of errors it has and if it can do something to repair it.