You can't play the movies from iTunes because the movies are protected. And if you want to play it on Xbox, you could use Leawo Prof. DRM to remove the DRM. https://www.leawo.org/tutorial/how-to-play-itunes-movies-on-xbox.html
To listen to music files encoded in Apple's AAC audio format, your Xbox
360 console will need the AAC codec (a processing file), which is
available as a free download from Xbox LIVE Marketplace.
Go Here: Instructions
http://support.xbox.com/support/en/us/nxe/gamesandmedia/sharingmedia/ipod/useappleipod.aspx
Hope this helps.
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