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Jul 5, 2012 7:55 AM in response to 59lawsby planb77,Read this article related to your issue. You may be trying to sync the High Definition (HD) version of the TV Show to your device. The iPod classic does not support HD content. You'll want to download the SD version instead.
iTunes: May be unable to transfer videos to iPhone, iPad, or iPod
To prevent HD versions from being downloaded in the future head to the iTunes Store, click the Purchased link, and then select TV Shows and remove the tick mark next to Download HD when available. You should be able to download the SD version now from under this same page.
B-rock