Ipod/itunes won't play videos

Hello,
I hope someone can help me before I either go completely insane or throw this ipod out the window. I just received a 3rd gen which replaced my original 2nd gen nano. I registered it and it shows up as a 3rd gen ipod (icon, etc) however, when I downloaded video's to my itunes library and drag them to my ipod I get this error mess. "_ cannot be copied because it cannot be played on this ipod" I can't even watch the videos in itunes???
I'm running itunes 7.5 with OS X 10.4.11. I've updated all software and have restored the ipod several times. I've also had my music wiped off after plugging it back in. Am I not doing something in itunes? Is the ipod defective? Help!
Thanks
Michele

I was having the same problem and then I disovered a program called iSquint. This will convert all popular formats including FLV for playback on iPod Nano. Best of all it is freeware

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