Having trouble moving show to Ipod Classic

For some reason, I'm having trouble moving a purchased TV Show (Dr. Horrible's Sing Along Blog) to my Ipod. Everything else has transferred fine, but this just stays in Itunes and wont go anywhere. There's more than plenty of room available, so I'm not sure what the deal is. Any suggestions?

Hey, I had the same problem too, so I changed to option to sync all episodes instead. All 3 episodes are up, but they can't play on my iPod (iPod classic 5th gen 30gb). When I click on an episode to play it goes into the movie screen like any other movie but the screen just remains black for more than a few minutes. Anything I do to get it going just brings me back to the list of episode pages.
I've tried removing the show and re-syncing my iPod but to no avail. Can anyone help?!! I really want to watch Dr. Horrible!

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