Song plays on iTunes but not on iPod ...

My apologies if this has been answered before, but I couldn't find anything similar on the search.

I have one particular song that simply will not play on my iPod. If I select it, the artist, song title, and album title all show, but the album artwork does not load, and after a second or two the pod will just cycle to the next song and play that one instead. This song plays fine on iTunes. I had an issue previously with songs that suddenly stopped playing and I resolved it with MP3 Validator (something about corrupt tags if I remember correctly), so that song has been put through there and like I said, plays fine in iTunes. This song was not purchased through iTunes. I just recently upgraded to version 9.0.1.8, but the problem has been present since before the update. I tried deleting the file, re-adding it iTunes, and re-syncing the iPod, but that didn't work. I have a 30 gig video ipod.

I'm stumped. All the other songs on this album play without difficulty.

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