Seriously, I'm having trouble finding interesting stuff for my video
iPod that's freely (legitimately) downloadable.
 I recently heard that some universities are making video courses available.
 I'm also interested in commentary, short films and the like...

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Request for Question Clarification by tutuzdad-ga on 01 Feb 2006 06:55 PST

Would this work for you as an answer?

Free Movies - Entertainment Magazine
http://emol.org/movies/

tutuzdad-ga

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Request for Question Clarification by tutuzdad-ga on 01 Feb 2006 06:57 PST

Here's another one. Let me know.

PUBLIC DOMAIN TORRENTS
http://www.publicdomaintorrents.com/
(500 downloadable programs in the free public domain)

tutuzdad-ga

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Clarification of Question by pcventures-ga on 03 Feb 2006 12:35 PST

I'm a bit more interested in stuff that's ready immediately for the
ipod, educational content (University lessons done as vpodcasts, for
example), and other independent video content.

Lots of good stuff on http://www.atomfilms.com/af/home/
you may have to convert formats of course (swf to avi to mov or
mp4)...tools are here
http://www.videohelp.com/tools?convert=SWF%20to%20AVI

mp4 is not the most common video compression (yet) so you'll have alot
tougher time if you don't want to convert.

I, for instance, just set up my convertor program to chug away over
night (batch processing multiple files or tv shows) and it's all ready
the next morning.

Search on ISOHunt.com some contain the word iPod in the title.

Please be aware that ISOhunt is a bittorrent and likely contains
copyright material.  Many items on bittorrent sites are not
legitimately available for download as the question asked.

You can get your DVDs onto your iPod FREE here: www.ePodSupport.com