Video Transfer To Classic 160?

Just bought a new 160GB iPod Classic.  Please excuse my ignorance, but I'm trying to put a NCAA produced video sporting event on it and can't figure out how to do it after reading the on-line manuals.
I load the commercially made video disc into my computer, with the iPod connected, and there's no prompt to begin transfer/import to the iPod. 
I've already loaded roughly 400 music CD's without any problems.  Is this type of video something the Classic wasn't designed to accomodate? 
Thank you for any/all help/advice!

Will the video you purchased play in iTunes? If you haven't tried it, try playing it in iTunes first and then see if it will transfer.

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