Lessons from the Disney Villains: Cheshire Cat



Not every villain has to be conventionally “evil”

Now, now, please put down your pitchforks and torches. Trust me, I understand that, nine times out of ten, when placed on an old school alignment chart, our antagonists fall into some spectrum of “evil”, be it lawful, neutral, or everyone’s favorite – chaotic. But this does not always necessarily have to be the case.

Throughout life, every person encounters an opponent, one with the intention to inhibit their inevitable success. However, there are those who we meet along the way without blatantly ill intent whose interactions with us can cause us to stumble, to stop, to question truth. These encounters may mean no malice, but nonetheless, they impede progress and serve as obstacles to overcome. Or, other times, they may leave the hero – and the hero’s audience – with an inexplicable, but irrefutable, sense of vexation.

This is the strength of the Cheshire Cat.

Let’s take a look at Cheshire Cat, shall we? At the outset of Alice’s journey in Alice in Wonderland, the audience is led to believe that Cheshire is a sort of ally of Alice’s. Harkening back to the Scarecrow of Wizard of Oz, he points our distressed heroine in the right direction – or so we believe. As every good villain does, Cheshire allows us to believe that, despite his unsettling quirks, he means our damsel well.

Despite this, once Alice reaches her destination at the Queen of Hearts’ Castle, Cheshire causes all sorts of chaos, from exposing the Queen’s bloomers to insulting the Queen on behalf of Alice. On one hand, his actions almost cause the death of the heroine. On the other hand, Cheshire’s intention appears not to be to doom Alice, but rather to simply stir up some trouble, make a little mischief, cause everyone to be just as mad as he himself is.


When writing antagonistic characters, we must ask ourselves: what is the intention behind their actions? Do they loathe those they impede, or do they hold simpler intentions? By no means must these intentions need be pure: Cheshire’s wish to upset the fragile balance of Wonderland certainly does not seem noble by any means. However, that does not mean their intent is to harm the protagonist. The protagonist is but a pawn to them, a means to an end. In some cases, their “toys” are but obstacles to push about the playing field until they reach their goal.

If Cheshire were a Dungeons and Dragons character, his alignment would likely fall much more along the lines of “Chaotic Neutral” than any sort of “Evil”. Despite this, he poses a serious threat to our heroine. So, is he a villain? A hero? A mentor gone wrong? Or does he exist somewhere in the middle: an entity without classification? Sure seems fitting for one such as he, no?

As authors, we must remember that not all enemies wish our heroes harm. Some people seek to manipulate the protagonist. Some seek only their own gain, whether it be helping the protagonist (even temporarily), or turning against them – or both, at different times. These people are not evil, nor should they be treated as such. Misguided? Maybe. Remember to fill your world with enemies of all sorts – not solely those wishing for world domination and the death of benevolence.


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