Trouble transferring videos purchased in iTunes to video iPod

I found this to be a bit curious. I just purchased the White Stripes' "Hardest Button to Button" video in iTunes (along with 4 other music videos from other bands), and I was unable to transfer the file to my video iPod (the other four videos transferred without problem). The message said that it could not be played on this iPod. Is this a widespread or unique problem? I thought all videos purchased on iTunes were compatible with the video iPod, if not, is there a way to determine this before purchasing? Is there a way to solve this problem without purchasing additional software?

Unhelpful boilerplate response from the iTunes customer service team below. I have all of the updates (for iTunes & video iPod) and still no luck. I've even done the restore to factory settings thing, and also, no luck.
Has anybody else encountered this quirk (see my original question) and managed to work around it without purchasing any additional software?
From iTunes customer service:
Dear Customer,
We're sorry you're having trouble transferring music to your iPod. Here are
some resources that might help resolve this issue.
If you have never transferred songs to your iPod before, read this short
article to get started:
http://www.info.apple.com/kbnum/n165242
The most common reason songs won't transfer is that the iPod software or
iTunes is out-of-date. Please visit these links to download and install the
latest version of the iPod's software and iTunes.
iPod: http://www.apple.com/ipod/download
iTunes: http://www.apple.com/itunes/download/
If you have never updated your iPod before, here are easy instructions to
walk you through the process:
http://www.info.apple.com/kbnum/n60944
If you have the latest version of iTunes and the iPod software, and you
still can't transfer music to your iPod, please read our troubleshooting
article on this subject:
http://www.info.apple.com/kbnum/n93867
Sincerely,
The iTunes Music Store team
http://www.apple.com/support/itunes/ww/

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Trouble transferring videos purchased in iTunes to video iPod

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