How can I get all the songs from iTunes library into my Nano?

Question

My iTunes library says it has 430 songs, but when I hook my
Nano up, they don't all go into it. And I've tried checking and
unchecking the box next to it in the library. Some have gone in
and some haven't. It says it's updated, but it's really not. For
instance, I have 12 Eric Clapton songs in the library, but only
4 of them made it into my Nano. Does it have to do with where
they came from? I have some recorded from my CD's, some
I purchased from iTunes, and some I downloaded on Limewire. I believe most of them that didn't go in came from Limewire. But why would they be in the iTunes library and not go into the Nano?Please help me if you can!
Thanks!

Answer 1

well if you want EVERYTHING than you should connect your iPod and go to summary, then you should look at the summary at the bottom, it will say sync checked items. if you have already checked all the ones that you want then you click it and then click apply hope this answers your question!!!

Answer 2

you should try restoring your, ipod, try this address http://www.apple.com/support/ipod/five_rs/
i think another problem shoul be the tags of the songs, so the songs are really passed to the ipod but when you look up by artist you don't find them cause the tags are bad