This thread's probably gonna get moved since it's not about Mac Pro's, but....
Is the Video in the proper format for the iPod? Ie. MP4 with the proper frame-rate and size?
As well, as far as I know, you don't drag things to your iPod, you ask iTunes to sync stuff to your iPod. iTunes usually automatically syncs things to your iPod. You specify what types of things you want sync'ed (music, TV shows, movies, etc.) on the windows that show up when you click on your iPod in iTunes.