Videos will not work!

I'm having 2 problems with videos:
1. About fifteen of my videos will not transfer to my ipod, when I try to drag and drop them nothing happens at all. They are in the correct format (mp4) and ten other videos had transferred without a problem, just for some reason those fifteen will not. How do I get them on my ipod?
2. I downloaded a movie from itunes and it transferred to my ipod fine, but when I try to play it on my ipod all it does is shows a loading screen, then turns black and freezes my ipod. What's wrong here, and how do I fix this? This one should definately fit the specifications required for ipods because it was purchased from the itunes store.
How do I fix this?

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*https://support.mozilla.org/kb/Safe+Mode
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