IPod and Videos:  How to Update and Play

My brother just got a new iPod. Upon synchronization the iPod was updated with his music but not his videos. Basically all of videos are movie trailers. What does it take for iTunes to take them into account when updating the iPod? And will any video (let's just limit to movie trailers for starters) play properly on it?
At this point I have to say that right out of the box the iPod was "paired" to my PB's iTunes and it did play videos then. Then, after some struggling, I managed to restore the iPod to the factory settings to pair it to his HP Pavilion laptop. Here's where iTunes and iPod are failing, like I said, to update the latter with the music in the first.
Thank you very much. Happy 2006.
George...

Restore your iPod nano to new condition with a $4 can of Brasso

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