I'm not much for hyping other links, but one of the funniest series about gaming ever was Misadventures in Gaming by Dan Bosley. The original 19 were on the Terminal City Gamers web site, which is now defunct. Actually, they kind of bogged down in the middle as Dan went on some fantasy trip about one of his guests cheating at David and Goliath, but overall they were a riot. A complementary series about Staging a fake Murder at a restaurant was also really good (again, slightly ruined with some over-weirdness at the end).
A one off new episode was on the Games Journal. It was quite funny.
Now there is supposedly a new series starting on Gamefest. The first episode is here. Let's hope it continues.