The Octopus Rule, or: So Your Druid Wants to Be an Owlbear
This title isn't going to make any sense until I get into it, so bear (haha) with me.
I was recently reminded of the discourse that exploded online when the trailer for Dungeons & Dragons: Honor Among Thieves came out, and featured Doric the druid wildshaping into an owlbear.
Objectively, that moment is radical as fuck and one of the most fun moments of the movie itself. But the reason it caused a huge stink is because: druids can only wildshape into anything categorized as a beast, while owlbears are categorized as monstrosities. So the rallying cry from rules purists is that this is impossible and inaccurate and a clear indicator that the writers don't know what they're talking about and the movie sucks! Baaaaw!
But if you're one of the many (potentially new) players who saw that scene and said "but I wanna be an owlbear!" fear not; this isn't as rigidly forbidden as these spoilsports say it is. There are absolutely ways to make this happen, and it starts with a DMing mindset that I call: the octopus rule.
In season 2 of Bluey (stay with me on this), there is an episode called Octopus, where Bluey and her playmate Chloe play the titular game, Octopus. It's a fairly loosely defined roleplay where Bluey's dad, Bandit, burbles and flails wildly while trying to fend the girls off from trying to get to the other side of the couch he's guarding to collect his buried treasure. Chloe has so much fun with this game that she tells her own dad about it, trying to get him to play, but her father is a very practical, reality-minded person - er, dog - and has trouble visualizing what Chloe is describing, and keeps asking "wait, do octopi do that?"
Chloe eventually gives up, disappointed. Her dad feels bad and spends the evening researching octopi, eventually showing her some of the more interesting things he found. It turns into them brainstorming some new rules for Octopus using the information they found - such as being forced to freeze if the octopus touches you, inspired by a particular type of octopus that had poisonous suckers. It makes the game accessible for Chloe's dad, and even more fun for the girls when Bluey comes over to play. And one of the rules they decided on was, that if the question "do octopi do this?" came up, the answer was:
Our octopus does.
And that line is what altered my brain chemistry when it comes to discussing D&D rules, rule of cool, and all that paperwork that gets in the way of doing something interesting in the game. The rulebook might say one thing, but you might think that it makes more sense or is more fun to be another way. Or someone might ask a question about something that might work one way in reality, but maybe your world works differently. So, the answer is: if it's more fun, tells a better story, and keeps you from bickering with your players all day, then yes, it does work that way.
Example: In Forgotten Realms, drow quite famously live primarily in the underdark, most likely in the city Menzoberranzan. But what if you're not playing in a Forgotten Realms module? You don't have to adhere to that.
"I want to play a drow who lived in a little village in the deep dark woods."
"Do drow even live in the woods?"
"Our drow do."
I even invoked this during my mom's campaign. My bardlock got a warning from a higher power that doesn't really understand how the world works that asked if she knew that her brother "was involved with a fiend." This was a scary plot point for a while because she had recently broken her pact with a fiend, and was worried that this meant someone was manipulating or hurting her brother. But when we went to visit him to make sure he was okay, it was a false alarm; his boyfriend was just a werewolf, and one who was aware of his condition and had safety measures in place. And as I say that you may notice a flaw in that: werewolves aren't fiends - they're only listed as humanoid and/or shapeshifter in the books. Turns out my mother had misread or misremembered their classification. But none of us criticized her or argued or even demanded any sort of retcon; her game is set on an entirely different planet, how do we know that werewolves aren't fiends in this world? So I simply stated: "our werewolves are."
"BUT SARIA!" I hear some of you cry, "THE RULES ARE THERE FOR A REASON! CHANGING THE RULES JUST CAUSE IT'S FUN WOULD CAUSE ANARCHY! ARE YOU SAYING WE SHOULD JUST LET A DRUID PLAY AN OWLBEAR WITH FULL MONSTER STATS?!"
No, not at all. Of course there would be reasons not to give your druid full owlbear stats. I'm just saying that if you let one word in the book deny your player something they're excited about, you could afford to think more creatively. If your character wants to be an owlbear, find a way to make it happen! The easiest way would be a cosmetic change; they can say they're wildshaping into an owlbear, and in game they LOOK like an owlbear, but mechanically they have the stats of a brown bear - similar, but lower CR, and an actual beast. Maybe you can have them go on an epic quest to unlock a more powerful form and become an owlbear, but with tradeoffs such as limited use or giving points of exhaustion. Maybe you could make or find a PC build to play an ACTUAL owlbear (those builds exist, ask your local furries) that wildshapes into other forms. Be creative! Don't let the word 'monstrosity' be the end of the conversation! Your players want to do something fun, and you as the DM are the facilitator of fun.
Can druids wildshape into owlbear? Maybe your druids can.