Hey there ckhoury13,
It sounds like your video files may be incompatible with iTunes. Here is an article that will help you determine if your video files need to be converted before they can be moved into iTunes:
iTunes: Frequently asked questions about viewing and syncing videos
http://support.apple.com/kb/HT2729
- Video content purchased from the iTunes Store.
- QuickTime and MPEG-4 movie files that end in ".mov", ".m4v", or ".mp4" and are playable in QuickTime Player.
- Video podcasts.
- iTunes Digital Copies.
- iTunes Store Movie Rentals (Requires iTunes 9 or later).
- Video content purchased from the iTunes Store.
- Videos that have been shared to iTunes using QuickTime Player (Mac OS X v10.6 Snow Leopard).
- Videos that have been re-encoded for iPod with QuickTime 7 Pro.
- Videos that have been re-encoded for iPod with iMovie, Final Cut Pro, and others. Refer to Exporting a movie from iMovie HD to iPod for an iMovie HD tutorial.
- Video Podcasts that have been created for mobile devices.
- Video files after using the iTunes File > Create New Version > Create iPod or iPhone version option.
- Video files after using the iTunes File > Create New Version > Create iPad or AppleTV version option (iPad and AppleTV only).
- See below for detailed movie specifications.
- iTunes Store Movie Rentals (Requires iTunes 9 or later).
Take care, and thanks for visiting the Apple Support Communities.
Cheers,
Braden