Album Artwork trouble

This isn't a huge deal, but it's still really annoying. Anyway, I noticed that the album artwork for some songs would not show on my ipod (even though it did show in iTunes)
So, I tried unchecking "display album artwork" which told me that all the artwork was being deleted (even though it is still technically ON my iPod... the artwork still shows in iTunes) and when I tried to synch the artwork BACK, it said it encountered a -50 error about 75% of the way through. So... now the album artwork on my iPod doesn't work for any song and I have no idea what to do.
Someone help, please?

I don't use a Windows machine but my guess is that your songs never have album arts attach to it. Maybe Windows Media Player has those albums arts. If you have an iTunes account, you can download album arts for free. In iTunes go to Edit>Select All then go to Advanced>Get Album Artwork.

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