Moving movies from iTunes to iPod (6th gen 160gb classic)

Ok, so recently I've been having trouble with the transfer of my movies to my iPod (I have about 40 movies/TV shows on it already that I've never had trouble with)
Ex: I have a few episodes of Boy Meets World(not purchased from the iTunes store, but all of them play perfectly fine in iTunes). I put them into a new playlist, selected them all, and dragged the playlist onto my iPod. The issue is that only SOME episodes transfer and there aren't any error messages or anything, they just don't go on my iPod. **I also tried adding them one by one and it still doesn't work.
I have PLENTY of room left on my iPod for the episodes, they just won't transfer and I don't know why.
Is it my iTunes (meaning I should probably re-install it), or is it my iPod?

is your iTunes set to sync all content to iPod or only sync checked items?
Do you get any error messages stating that the video cannot be played on your device?

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