Yes the Ipod Classic will play any video or movie it just needs to be in the right format. I think the Ipod will play only mpeg-4. Handbreak is good if you are on a Mac I am not really sure how the version on windows is. The last time I used it the release with the interface had just came out and a lot of the buttons were grayed out. But that was a while ago and I haven't used my computer running windows in ages because I use a mac. (I hate windows, or anyting microsoft for that matter). Anyway to load a video all you need to do is load it into itunes much like you would music. Then transferring it to the pod is pretty much like transfering music. If the ipod can't play it back it should give you an error saying that the ipod is not able to play back.