How many of y'all played D&D back in the day? OK, not many.
Well, I think you'd still enjoy the podcast of the gentlemen of PvP and Penny Arcade (three online comic strip artists, two comic strips) playing the new version of D&D with a dungeon master from Wizards of the Coast (current developers of D&D). It is, essentially, listening in on a bunch of silly geeky guys play a role playing game. Once in a while they get kind of vulgar, and only once was it a little dull (I don't know why, I think they just got too serious about the fight and stopped the play acting and silliness. It may have something to do with the DM, who switched midway through the series). One of the guys from Penny Arcade is a geek, but had never played D&D before, so his reactions are interesting (plus, it means there is a lot of explaining how things work in the early episodes). Since they are cartoonists, each episode is documented with a drawing or two depicting something that happens during the episode. It's fun to have going on in the background while you're doing something else.
Series 1: Episode1, Episode2, Episode3, Episode4, Episode5, Episode6, Episode7, Episode8
The second series adds Wil Wheaton (of ST:TNG and general sci fi blog geek fame). The silliness continues with the better DM and a better balanced game. Wil makes a great addition, as he's obviously experienced in gaming and role playing and also less likely to be distracted by drawing cartoons during the game. There's some great teamwork too. I love the way they discuss things before taking action. There are two bursts of highly vulgar talk, followed by lots and lots of giggling. Rudy the Undead Hound (ep 7) nearly brought me to tears and a series of very unfortunate rolls of the dice in episode 8 made me giggle so hard my face and diaphragm hurt. There is lots of geeky gaming humor and they're obviously having lots of fun. I downloaded it for my entertainment files and really hope they come out with another series. Hilarious!
Series 2: Episode1, Episode2, Episode3, Episode4, Episode5, Episode6, Episode7, Episode8
Edited to Add: I'm listening to these a second time and the second series is definitely funnier than the first, but the first has some good info that helps you to follow the action.