Castle GreyHawk: The Thor Ragnarok of Old-School D&D Adventures From Back in the Day

One of my players asked which was my favorite module of all time? I thought about this question for a second and then answered with a question: Does it have to end in the night or can go on for as long as it needs to? Because if this module has an unlimited time frame, my answer is Castle Greyhawk.

Surprised by that answer, she then asked what makes that adventure so special? Especially considering how much D&D material I’ve read over the years. Well, grab a chair and a coffee as I attempt to give the question the proper justice it deserves. 

Just for some context, Castle Greyhawk isn’t really just a module. It was written in 1988 as more like an entire campaign setting that takes the players through levels 0-25. But wait, there’s more: While there is a castle called Greyhawk, it is ironically not where the lion’s share of the adventure takes place!

The overall premise is this: Extremely unusual monsters are emerging from the castle dungeons, and your party has been hired to put a stop to it. The castle has twelve floors below it, and each was written by a different author. The deeper you explore the levels, the more they become increasingly difficult and can be run entirely separately or in succession.

So, if you wanted to start a new campaign, the party would begin their training on the castle grounds. But, if you had a seasoned group who were looking to try something new for an evening, you could run them through level seven. 

The Value of Humor Is Not to Be Undersold

Castle Greyhawk did for D&D what Ragnarok did for the Thor franchise. Most people enjoyed the first Thor movie, although the second film left them feeling like they just watched an underwhelming sequel. However, the third movie, Ragnarok, was an enormous success that hit all the key story notes while appealing to a wider audience base. And there are a lot of reasons for this success, such as directing, casting and writing, to name a few.

The writing took a new approach by adding humor into the mix. Sure, it’s an epic superhero movie about Gods and the end of the world, but it didn’t take itself too seriously. This is brilliant, because it didn’t force the movie to commit to one particular style, and thus included viewers who might not want to watch a grown man with a helmet smash things with his hammer for two hours.

Instead, the scenes transitioned from action to comedy to drama and then back to action again seamlessly. Castle Greyhawk did the same.

The Introduction of Pop Culture in Fantasy 

You might be asking yourself, “So, they added some elements of humor into these adventures. Is that what made them so great?” And yes there are tons of nerdy game jokes along with a lifetime supply of puns, but that still isn’t it. What made Castle Greyhawk unique was its use of breaking-the-4th-wall comedy that would have impressed even Deadpool. In these adventures, no other franchise is safe from getting spoofed, referenced or made into a joke for your players’ amusement. This includes the Ninja Turtles, Star Trek, classic Marvel and Looney Tunes, just to name a few. 

But the madness doesn’t come close to stopping there. In one level of the adventure, all the monsters are made of edible material like cookie dough, or gingerbread. While in the next, the players could find themselves on a game show. Or even on the set of a movie with the famed wizard Mordenkainen himself.

However, while there are jokes, the threats are real and extremely deadly, as are the impressive and equally ridiculous rewards. So, if your group isn’t afraid of throwing down with a group of Daleks who really got off at the wrong exit, you might have come to the right party. 

Let’s Do Something Different 

One of my hallmarks of running games is scenery changes – because there is nothing quite as exciting as being in a desert for 11 sessions, am I right? One thing I already mentioned that was masterfully executed on this project was that no less than thirteen different authors put it together. So, if the style or flow of one floor wasn’t working for you or your players, you could just move to the next one without derailing the adventure.

In this way, the scenarios, settings or jokes couldn’t possibly get old because everything kept changing faster than a low-level, AD&D wizard could run out of spells. And while the players could run through a game that lasts a single night or an entire campaign, both the action and the laughter had very few slow points. 

As far as running Castle Greyhawk from the DM’s perspective, as long as you’re immersed in the humor and culture of the time, then the prep time will be minimal. Many of the scenes are their own one-shot gag. Amazingly enough, this allows everything to run together in a smooth, light-hearted montage of real-world comedic events with a fantasy spin on them. All of which will keep the players guessing without dissolving into a sequence of cheap gotcha moments. 

In Conclusion 

Castle Greyhawk is easily the funniest piece of material that Dungeon and Dragons, or quite possibly any actual gaming company, ever produced. And I’m not saying this lightly because there were some funny moments in the story here or there – rather, the humor is from beginning to end and, in my experience, humor done right can really add to the game. Because no player was ever in a game where they laughed all night and then said “That kinda sucked” the next day.  

So, if you are a serious player who enjoys only rolling with dramatic stories or isn’t all that familiar with some of the pop culture references from back in the day, this might not be your bag. However, if you are, then I highly recommend that you check out the Castle Greyhawk PDF, because it’s solid gold. Just prepare to have your mind blown that this 4th-wall-breaking, holy grail of comedy was actually a licensed Dungeons and Dragons product.