If you have iTunes 7 or later, click here for steps to sync video.
If you have a Fifth Generation iPod, you can use iTunes to add or sync videos to your iPod just like you do with your music. If you've set iTunes to manually manage your music, you can add videos to your iPod in the same manner—just drag and drop videos or a playlist of videos onto your iPod icon in the iTunes Source pane.
If you've set iTunes to automatically sync music to your iPod (or you've set it to sync music in selected playlists only), you've already done half of what's needed to sync video to the Fifth Generation iPod. Here's how to complete the process.
Once you close iTunes Preferences, iTunes will begin updating your iPod based on the preferences you've selected.
Note: If you manually manage your audio files, you must manually manage your videos. If your iPod automatically updates your audio files, you must choose one of the two automatic update options for video or choose not to update videos. If the iPod is linked to another iTunes library for automatic music syncing, you must change the link to the current iTunes library or change the music sync setting to manual in order to sync videos to the iPod.
For additional information about using your Fifth Generation iPod, see the iPod Tutorial.