How to Put Videos on an iPod
Locate the heading titled Library, located on the left hand side of the iTunes Window. You should see several options listed under Library, including Music, Movies, TV Shows, Audiobooks, etc... Select one of these source options to display your according Movies, TV Shows, Videos, Music Videos, or any other playlists that you have created, in the main iTunes Window.
Select any movies, videos, or music videos that you would like to add to your iPod, and drag them to your iPod icon, which should be listed under Devices, in the left hand side of the iTunes Window. iTunes should now start adding the videos to your iPod.
*If you want to select multiple videos, Command-click items on a Mac or Control-click items in Windows. From there, you can drag them onto your iPod icon in the Source list.*