Hanging around some iPOD forums, I have come across some good and some not so good software to convert video to the format needed for the iPOD Video.
Videora iPod Converter is a free video conversion application developed by the creators of Videora. It allows you to convert your regular PC video files (avi, mpeg, etc) into the proper video format that your iPod understands. iTUNES can play many different types of video formats but the iPOD Video cannot. I haven’t used it because I don’t have an iPOD Video, I have the Nano, but from what I have read it’s pretty good.
The Videora website also mentions the ability to search and download movies but I don’t know about that.
get it here http://www.videora.com/en-us/Converter/iPod/
and a great guide is here http://ilounge.com/index.php/articles/comments/video-to-ipod-conversion-for-windows-pcs-parts-2-3/