Though I have never actually played a game (though I really do want to) I am still heavily intrigued by the whole D&D/Roleplay/Tabletop Game phenomeon.
A couple things I've been following have given me, at least, a bit of a taste of the game and are pretty good to help get an idea of the experience for those who don't play these sorts of things commonly:
-The Penny Arcade/PVP (and Wil Wheaton) Dungeons and Dragons Podcast series:
Essentially Mike Krahulik (Gabe from Penny Arcade), Jerry Holkins (Tycho from Penny Arcade), Scott Kurtz (from PvP), and Wil Wheaton (Series 2 onwards) playing a series of campaigns of "D&D 4th Edition" together, some for their first time, with Chris Perkins (R&D of Wizards of the Coast) as the Dungeon Master.
You don't really need encyclopedic knowledge of the game or have to like their associated works to still enjoy the stories, trials and mishaps and various obscure geek-out moments that ensue. And, as webcomic artists are involved, there's plenty of illustrations of choice moments as well.
I should warn you that there is a bit of mature language (the atmosphere is pretty casual between them after all) so it's a little NSFW and discretion is advised.
The first two series of adventures of Acquisitions Inc. can be found
here.
The third series is under the Hide tag.
[HIDE]
Episode 1
Episode 2
Episode 3
Episode 4
Episode 5
Episode 6
Episode 7
Episode 8[/HIDE]
Check them out.
-Also I've been reading:
DM of the Rings (What if the The Lord of the Rings Books/Movies didn't exist and were a part of a D&D campaign?)
and
Darths and Droids (Same thing only with Star Wars, (the lack of Star Wars changes alot of Sci Fi history if you think about it) with lots of poking fun at Star Wars and Tabletop Gaming tropes, overall)
All of them I've found pretty enjoyable, even though I'm not actually an active player. But what do you, more experienced guys, think?