Can't transfer video to ipod classic

I recently added 6 new videos to my Itunes library. When I tried to manually transfer them to my Ipod Classic only 1 of the 6 shows up on my Ipod. When I drag any of the other ones over it shows the little green plus sign, but never has the spinning circle that shows it's adding it to the Ipod. All of the videos are the same format and all will play through itunes. I tried resetting the ipod, but no help. Any suggestions?

I figured it out. I went to play the video directly from iTunes rather than trying to transfer it to the iPod. I got a message I am not authorized, just like before. But this time it asked me if i want to authorize it. I clicked yes, obviously and voila...successful authorization. Now I can play it on my computer and iPod. Sorry for wasting everyone's time with this.

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