Why can't I put movies on my iPod Classic

I have the current generation of iPod classic and I want to put the Godfather trilogy that I have recently purchased from the itunes store onto the ipod, but everytime I do it tells me that I am not authorized to play them on this computer. I have deauthorized and reauthorized this computer with the account that I used to purchase the movies and still it will not let me put them on my classic. The ipod and itunes are completely up to date. Please help me if anyone can. thank you.

The files are fine because I can watch them on my computer without difficulties. I just don't understand why they wouldn't be compatible on the ipod classic if I purchased them from the iTunes Store with the same apple ID that is used across all my devices, which are all authorized to play my iTunes media. I mean the error that comes up is saying that my computer is not authorized to play them, even though I just watched one of them yesterday.
So confusing...

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