Cant get videos on ipod

i bought 2 seasons from itunes and i cant get them on my ipod. this is the first time i bought any videos from itunes. i have tried converting them for ipod and it give me an error saying :
error occurred while converting the file "Smug Alert!". An unknown error occurred (-50).
Also, when i plugged in my ipod i got an error saying:
some of the videos in your itunes library, including the viedo "Stanley's Cup", were not copied to the ipod "xxx's ipod" because they cannot be played on this ipod.
im almost positive my ipod plays videos. Also when i look at my ipod under devices on the left hand side of itunes it gives me the otion to restore my ipod to its factory settings. im not sure if i should do that. any help would be greatly appreciated.

"im almost positive my ipod plays videos
If you're not sure which iPod you have (you need a 5th Generation iPod to play video) then have a look at this page and you can check: Identifying different iPod models

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