Some friends and I put together a new piece called Law & Orcdom. It looks at the world of law enforcement in a world of high fantasy, with stories ripped from today's sourcebooks. The first case is the murder of a red dragon using an illegal rules exploit. I used D&D simply because most people are familiar with it but I'm thinking about future shows based on other games.
http://www.slangdesign.com/rppr
I also posted a video in the D&D Fan Film contest. It's called D&D: The Best Game Ever. It's about a group of friends who discover D&D. I based the movie on common gaming pitfalls like railroading and adversarial gamemastering. I actually based this video partially on discussions from here and rpg.net about why games break down and how.
http://gamevideos.com/video/id/5428
The new URL for the video is http://www.gamevideos.com/video/id/6370
Bad chaos dragon - no cookie.