Loading Videos Onto my I-pod. I need Help

Everytime I drag some videos from my "Video section" onto my I-pod on the left side it says that My I-pod cannot play it. What is wrong it is a fifth gen I-pod video... I don't understand why it wont play videos please tell me what to do.
Also whenever I try to drag videos from my desktop (after converting them to i-tunes files of course) to my I-pod in I-tunes nothing happens.. please help me!

this should help
http://docs.info.apple.com/article.html?artnum=301461

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