IPod Nano 8gb Won't Sync Whole Library

I just got a new MacBook Pro and a new Nano and when I try to sync my library it syncs all but 2 songs and I dont know why. I am not out of space on my iPod it just won't put 2 songs on it and I don't know which ones they are. The first time it synced my iPod it synced all but one song now it is 2. All of my music is legit too. It is all imported from my cds or purchased from the iTunes music store so I know its not a corrupted file or anything. Any help would be greatly appreciated. Thanks.

Have you tried resetting your iPod or go through any of the 5 R's? You may also want to make sure your Library doesn't contain any duplicate tracks. If this is the case, then the iPod may be skipping duplicates. This may not be the issue, but it doesn't hurt to check. Got to the top of iTunes and select View-->Show Duplicates. Another question is something that may seem like a stupid one, but just checking all possibilites....do you have files in your library that are not music tracks? Such as videos?

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