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Mar 31, 2015 9:24 AM in response to denjan33by Brett L,Hey denjan33,
If you have TV shows that are not synced to your iPod classic giving the error message shown, it is generally because the file is in a format that the iPod is not able to play. See this article for a complete explanation -
iTunes: Videos may be unable to sync to iPhone, iPad, or iPod - Apple Support
As an example, high definition (HD) videos will not play on an iPod classic. See this article which includes information about downloading content at lower resolutions for use on the iPod classic -
iTunes: Sync purchased HD videos to iPod or iOS device - Apple Support
Thanks for using Apple Support Communities.
Happy computing,
Brett L
