I presume that you burned this video on a DVD and are having this error : "Can't play this content because it may not be supported. For more info, go to www.xbox.com/support. Status code: 69-C00D11E7".
As far as I know, if the video is from itunes, it has a DRM protection. Then you first you need remove the drm before you burn them to dvd.
This is the guide to burn DRM protected iTunes videos/movies/TV shows to DVD playable on home DVD player.
Whether a video is legal or not isn't the issue but rather that not all media formats are supported by the xbox. If you have a video you'd like to play (legally downloaded of course) all you can do is try it and if it plays great if not you'll need to do
some video converting research and teach yourself how to convert video files. You can search the web for a program called G-spot (yea I know weird name) which will tell you all the codecs in your file, video and audio and go from there. There are some really
easy one step programs out there that work great for converting.
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