Are they mp4? Check the settings in your iTunes to make sure the Video part is checked so they actually transfer video.
As for legal... Make sure the video is your own.. If they're someone else's property it's copyright infringement (from what I've heard).
I have an Ipod (video capable), and I'm wondering if there's any way to load in You tube vids. I found freeware that downloads the vids to my computer, and I can open them with Itunes, but for some reason, they won't sync onto my Ipod. Any suggestions?

Chowhound
Comic Vine
GameFAQs
GameSpot
Giant Bomb
TechRepublic