Movie purchased from iTunes no longer sync's to Apple TV/iPhone

I purchased the movie Iron Man awhile back, I was able to watch it via my Apple TV once, I don't sync, I stream. I was also able to sync it to my iPhone. I am un-able to do both now, the movie is still in iTunes and is only watchable via the computer. When the iPhone is connected, I place a check mark next to the movie to add and nothing (Yes, there is enough storage space), in the Apple TV Movie menu the movie does not show up in the list, but others I have purchased do. Please help.

i have 2 movies in itunes listed in the movies tab in itunes and it's showing up in the movies tab in the iphone tab as well but after i sync it, i still don't have the 2 movies show up on my iphone after i sync and disconnect the USB cable. i checked to make sure the check mark is checked for the 2 movies and also i have check mark for all movies and have it checked for individual movies but it still will not show up on my iphone. I actually have 4 movies and 2 are showing up on my iphone. the format is mpeg 4. it should move to the iphone but i tried so many times to sync it. i have done the drag into the genius tab but it won't let me drag directly onto the iphone icon in itunes. i don't know why the movies won't move onto the iphone. i have plenty of space on my iphone. any ideas what i need to do? i believe the movies are in the itunes library.

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