Currently Being ModeratedMay 6, 2013 12:37 AM (in response to shaymen)
If you use automatic syncing, you may need to set up the iPod's (and iPhone's) Movies tab in iTunes. I'll just describe for the iPod, because it's the same for an iPhone that is synced to an iTunes library. If your iPhone syncs to iCloud (not your computer), then it is different.
Select the iPod in iTunes. There is a row of "tabs" (starting with Summary). Click on Movies there. This is the Movies tab, where you tell iTunes how to sync movies to the iPod. Sync Movies is checkmarked.
If you want to automate syncing of movies, check the box for Automatically include [option] movies and select the desired option. Otherwise, you can select the specific movies you want on the iPod from the list shown below. Click Apply...
NOTE: When you click Apply, if you have been using the manual method to load the iPod for Music, the iPod's current music content will be replaced by selection of songs on the Music tab.
If you have been using the manual method (drag and drop items on the iPod in iTunes) to load the iPod, you can do the same thing with movies.