5- X-Files (Unusual Suspects) This one is lowest on the list only because it is such a small reference, in short the character of Langley (the blonde longhaired lone gunman) is seen in what appears to be a back alley game (maybe craps or even a dog fight) He states boldy that the odds are 200, and then questions everyones manhood when they don't put in their bets once they do, he roles the dice. It's a d20, and the people around him (as the shot pans out) are informed that they each lost 200gp (suckers) it's a classic misdirect but a lot of fun and completly within keeping in the game.
4- Dexter's Lab (AD&Dee Dee) This one shows that cartoon artist Gendey Tartakofsky knows what it's like to sit around a table fighting imaginary orcs for treasure. Dexter is cast in the light of a know it all DM ruining the fun for his players when his sister joins in, takes over as Dungeon Master and shows that the rules can go hang as long as the players are having fun (well except Dexter who is stuck playing Hodo, the furry footed Burrower!) great example of kids playing the game.
3- Community (Advanced Dungeons and Dragons) This one gets high marks just for it's clever use of turn around tactics. In the 1980s D&D was a scapegoat for many suicides and people like Pat Robertson, claimed it to be the work of the devil, and t was to blame for suicides. In this episode, Jeff finds out Neil (often called Fat Neil) is depressed because he is being teased at college after being tormented in high school about his weight, finding out that Neil is into D&D, Jeff concocts a game to help show him he has friends and stop him from potentially committing suicide. The only obsticle is Pierce the dickish. Classic.
2- The I.T. Crowd (Jen the Fredo)In this take D&D is analogized with prostitution with hysterical results. Jen is forced to show some businessmen a good time, meaning booze, hookers, and the like and after a disastrous attempt with them seeing the Vagina Monologues instead, she enlists Moss and Roy to play D&D with them. Which they get into, and find that D&D can be pretty fun too.
1- Freaks and Geeks (Discos and Dragons) This one is the top of the list in my opinion, and if you like D&D you owe it to yourself to watch this episode if not the whole run of Judd Apatow's amazing show Freaks and Geeks. Daniel (James Franco) is forced into AV club for punishment and has to hang with the geeks, while Sam and the guys are Nerding it up, the talk about and then invite Daniel to join in, and he does treating the viewer to what about every first D&D game looks like (especially in the 1980s) soda and chips, corny theatrics and rolling dice in the end Daniel admits it was kinda fun, but does not go off the deep end It's probably the most outright realistic approach to the hobby I have ever seen on T.V.