Surrender Dorothy:

What I Learned from Gender-Bending
a 100-Year-Old Children’s Classic

Theodore & Lolo

CAUTION: These observations about gender were written by a western, upper-middle-class, forty-three-year-old, straight, caucasian, cis male while wearing a Kevlar vest.

The Wonderful Wizard of Oz is one of the most popular and beloved children’s books of all time — and I decided to mess with it.

The Metamorphosis designed by yours truly for Big Fake Books and Records

It all started — as most things do — with me procrastinating. Instead of working on my own book, I followed Alice down a public domain rabbit hole. I decided I should find something free and short, tweak it in some simple way, and publish it on Kindle and iBooks as a test to see how everything works. The Metamorphosis by Franz Kafka was my first choice, because I had already designed a jacket cover for it years ago. But while it may be a short story, it is anything but simple. What would I change? How could I modernize it? And while the original German text may be in the public domain, were the translations also?

I eventually abandoned Kafka and the bug man, looking for something lighter and simpler to experiment with. I noticed that a lot of the popular public domain books were for children: Alice in Wonderland, The Adventures of Huckleberry Finn, and others. What could I do with them to view them in a new way? I suddenly thought of fan-fiction and Adventure Time.

Adventure Time’s Finn and Jake are mirrored by the gender-swapped Fionna and Cake

Adventure Time is a Cartoon Network phenomenon created by the incomparable Pendleton Ward. In an unconventional nutshell, it’s a story of a pre-teen boy named Finn and his thirty-something magical adoptive dog-brother Jake, who adventure in the post-apocalyptic Land of Ooo, often thwarting the plans of the tragic Ice King who is obsessed with marrying princesses. In the ninth episode of the third season, Adventure Time tried a very meta and self-conscious experiment: they did an entire show where the main characters were gender-swapped as Fionna and Cake, a young girl and her cat. In the end, it was all ‘fan-fiction’ created by the Ice King himself, but it set fans on fire and ignited a larger trend of swapping the sex of popular cartoon characters.

“Raging Bender” Episode 8, Season 2 of Futurama, first aired on February 27, 2000.

It is important to note that the term gender bender is somewhat controversial. Gender is (and always has been) a broad yet personal subject. As wikipedia notes, gender bending is “sometimes a form of social activism undertaken in response to assumptions or over-generalizations about genders.” This over-generalization includes the binary swapping of a male form for a female one (and vice versa). To underscore the complicated and multi-faceted nature of sexual identity, facebook allows users to self-identify with over fifty different gender labels. (The Daily Beast has a layperson’s breakdown here.)

Given the more sexually conventional and conservative nature of old children’s stories, it is still a very interesting experiment to make a binary swap of the most typical genders: what if the boys were girls and the girls were boys? How would we view differently Alex in Wonderland or Olivia Twist? The sexual prejudices and stereotypes could be uncovered and viewed in a different light. I decided to test this on the first modern American fairytale. I had no idea what I was getting into.

Original cover

Frank Baum wrote The Wonderful Wizard of Oz in the late 1890s. He was inspired by authors like Lewis Carroll who shunned the moral-laden fairytales of The Brothers Grimm and Hans Christian Anderson to write stories kids could enjoy. Baum thought Alice in Wonderland’s plot was gibberish, but he was in favour of its hero: a little girl. Young characters can accept the impossible, which helps to move the story along at a more adventurous clip. But little girls in particular lend an added vulnerability which allows the author to defy social expectations, especially in the early 20th Century. Dorothy and her ragtag band of strange (male) characters lead The Wonderful Wizard of Oz to become one of the most popular children’s books ever.

What’s in a Name?

Before The Wonderful Wizard of Oz was published in 1900, the name Dorothy was just a quirky form of the more common Dorothea. Just four years later, due to the popularity of the book’s heroine, Dorothy entered the top ten of girls names and stayed there for almost forty years.

Dorothea literally means god’s gift from the Greek words dōron (gift) and theós (god). If you swap these words, you get the male variant of Dorothy: Theodore. This discovery inspired me to see if I could gender-swap the entire cast:

Dorothy → Theodore
Toto → Lolo
Uncle Henry → Aunt Henrietta
Aunt Em → Uncle Ed
The Scarecrow → The Scarecrow (easy!)
The Tin Woodman → The Tin Woodswoman
The Cowardly Lion → The Cowardly Lioness
The Wicked Witch of the West → The Wicked Wizard of the West
The Wizard of Oz → The Witch of Oz
Glinda the Good Witch → Glendo the Good Wizard

It was surprisingly easy to do once I got the hang of it. But after the names I had to deal with the roles. That’s when things began to get more complicated.

On Witches and Wizards

Are all witches female and all wizards male? In the first Oz book this holds true, but in subsequent Oz stories wizardesses are also mentioned. When Baum wished to differentiate the good witches from the bad, he would later substitute the word sorceress. Also, some contemporary fan fiction adds the term warlock to the mix to denote a male witch (even though witch in the Wiccan sense is a genderless word).

I decided to change the four female witches into male wizards, and to make the titular Oz into a female witch. The Wicked Wizard of the West sounds different than The Wicked Witch and reminds the reader that there has been a change. I didn’t realize the full ramifications of this change at the time, or how it would alter the mood of the whole story.

I felt a bit guilty and awkward changing the title to The Wonderful Witch of Oz. Baum loved the word wizard. It was his starting point for the entire story. As Baum himself stated in a 1903 press release:

I have a little cabinet letter file on my desk that is just in front of me. I was thinking and wondering about a title for the story, and had settled on the “Wizard” as part of it. My gaze was caught by the gilt letters on the three drawers of the cabinet. The first was A-G; the next drawer was labeled H-N; and on the last were the letters O-Z. And “Oz” it at once became.

So you see, the real character here is that Land of Oz, not the witches or the wizards, the warlocks or the wizardesses. Oz was Oz was Oz. I continued with the swapping.

On Scarecrows and Cats and Dogs

When Dorothy sets off on her own, she meets her first companion in the form of a scarecrow. There is nothing physically distinguishing the scarecrow as male or female. It wears a blue suit and boots, something a woman could conceivably wear. It has a husky voice, which also pertains to actors like Kathleen Turner or Lauren Bacall. It simply refers to itself as male after it has been taken down from the pole it was trapped on.

“Thank you very much,” said the Scarecrow when he had been set down on the ground. “I feel like a new man.”

What’s interesting and unique in the original book, is that a little girl rescues this goofy, straw man. Dorothy is sincere and focused, whereas her companions are foils (characters who differ from Dorothy to highlight her better attributes) and fools (silly persons).

So here’s a thought: why does it feel awkward to have a young boy leading a foolish female? It’s because little boys are typically considered foolhardy and rambunctious and women are considered practical and nurturing. Men make good fools because they deserve to be taken down a few notches. We can laugh at their expense because they (and their egos) rule the modern world.

Dogs have owners, cats have staff.

Did you ever wonder why there aren’t more funny dog videos on YouTube? It’s because dogs are the most sincere animals on the planet. They don’t have egos and they live to please. The exact opposite is true of cats. Cats are generally aloof, trying to appear cool and in control, so when something happens to knock them down a few pegs we have no trouble laughing at their expense. I’m not saying women are dogs and men are cats, but I am saying that ego and self-importance (two typically masculine traits) are easier to make fun of than sincerity and family loyalty (two typically feminine traits). In television commercials, we often see the stupid Dads, but when have you seen stupid Moms? When you swap the genders, the stereotypes come more into focus. It’s much harder to laugh at a woman Scarecrow stumbling down the road, talking about how brainless she is, because many women struggle to gain the upper hand. We don’t find it funny to laugh at the underdog, but will gleefully LOL when the fatcats get theirs.

On Lumberjanes and Woodswomen

“Sexy” Lumberjack Halloween Costume

There is a disturbing tendency in Western culture to insist that the female version of something is also attractive or ‘sexy’. While it may be titillating for some, it is also insulting to young woman looking for career choices. You want to be an astronaut? Cool, so long as you’re a sexy astronaut. A lumberjack? As long as you wear thick make-up, short-shorts and a Daisy Duke plaid top. If you want to find a gender-offensive example of any stereotypically male vocation, just search for “[job title] sexy Halloween costume” on Google.

Woodswoman by Anne LeBastille, the authentic lumberjane.

When you swap genders of a central character, the biases of the time become more apparent. Why is a female lumberjack (made of tin no less) living by herself in the woods? Male characters are free to be hermits or loners. They have things to work out. Female characters, on the other hand, only live alone if they are: crazy, evil, or very, very old. A wicked witch could live alone, for instance, because nobody loves her. If a woman is kind and sociable, we expect them to be part of a family. The only other acceptable female loners are nuns: the saintly witches of the North and South. They are pure, divine (and presumably chaste) rulers, beyond the earthly pursuits of marriage and children.

In the gender-swapped version of this story, we find our Tin Woodswoman alone in the forest. At first this feels strange, but then we realize that she wanted to get married and live happily ever after but was severely tortured. All of her limbs were amputated, and her entire body was eventually replaced with metal parts. Metaphorically, and literally, the world has turned her into a cold, heartless, machine. Of course, she also happens to care deeply about the smallest creatures (she gets upset about accidentally stepping on an insect), and cries a lot of the time (which we’ll get to later).

This broken lumberjane gets paralyzed with grief, since her metal joints seize up whenever she gets wet from crying (which she does a lot). A battered woman with a broken heart becomes a much more tragic companion than her original male counterpart.

On the Mane Character and Other Hairy Problems

In the City of Oz, Dorothy’s party meets a soldier who is distinguishable by his facial hair, referred to as long, green whiskers. This is problematic when changing physical genders. If you keep the whiskers, then the character stands out as a genetic oddity. If you remove the whiskers, what physical attributes to you replace them with? In the case of this soldier, who keeps popping up throughout the story, I made him a her and presented her with long, green hair. This may seem slightly more common (and perhaps even a bit more sexist) than a fancy moustache, but it serves to identify her without drawing too much unnecessary attention.

The Cowardly Lion as illustrated by W. W. Denslow

The mane of the Cowardly Lion, however, presents an altogether different problem. While it is only mentioned 4 times in the entire story, it proves difficult to remove. Dorothy hangs onto it once while the Lion carries her over a chasm, and she snuggles up to it to keep herself comfortable at times.

The mane is also prominent in the illustrations by W. W. Denslow, the first illustrator of Oz. Denslow attempts to emasculate the scaredy-cat further by tying a bow to the lion’s mane and tail. The original lion is trying to regain his masculinity. What happens when he becomes a lioness? There is an entirely different dynamic. Now she is a bearded lady, purposely attempting to act less feminine, rejecting her ‘natural’ state. Perhaps it is the extra testosterone which is giving her a mane and causing her to act more aggressive? Regardless, she is suddenly more ‘freakish’, a genetic mutation. And while there are maned lionesses in the real world, according to National Geographic, they are anything but common.

There’s nothing wrong with a butchy lioness, but this stereotype now has a completely different meaning. We have switched from an effeminate male with something to prove, to a hairy woman trying to shed her femininity. We’ve gone from Kurt on Glee to Mellissa McCarthy’s character in The Heat. Both are clichés, but they come from very different cultural biases.

In the end, I left the mane unshorn.

The Clothes Make The Man/Woman/Boy/Girl

Just like hair, the wardrobe of a character can often reflect their gender. Dorothy wears a bonnet and a gingham dress. Theodore wears a cap and a checkered shirt. For other characters and cultures, I could usually swap a dress with a robe, or an apron with a vest.

The famous ruby slippers from the first Wizard of Oz movie don’t actually exist in the books. Unlike the movie they are referred to as “Silver Shoes”, which don’t stand out as too strange for a young boy to wear. However, “the child was so proud of his pretty shoes that he never took them off except at night and when he took his bath.” Is it strange that a boy should find his shoes pretty and never want to take them off? Not really, if you just consider pretty to be an old-fashioned word. Replace it with cool and I can easily imagine my son removing his Vans only for his bed or the shower (which he does). Regardless, I keep all adjectives true to the original text. My experiment was to swap the genders, not to modernize the language.

Still, it made me think about how clothing is used to make you feel comfortable (or uncomfortable) with different characters or cultures. It is also a clear way to differentiate them from others. Aside from the Silver Shoes, there is only one other indispensable item of clothing in this story: the Golden Cap which commands the Winged Monkeys. Luckily a cap can be worn easily by anyone without raising eyebrows.

Dorothy is dry-eyed while all the males surrounding her are weeping.

Boys Don’t Cry?

I never realized how much crying happens in this book until I swapped the genders. Interestingly, Baum has the three male companions crying throughout the journey. This makes them sympathetic and less of a threat to Dorothy. When they are the female companions to Theodore, they instead look a bit weepy and over-emotional. The Scarecrow “wails” selfishly when she finds out that Oz is a fraud and she won’t get her brain. The Cowardly Lioness cries when she first explains how terrified she is of everything. Then later she cries in sympathy as the Tin Woodswoman is being repaired. Her tail is consistently wet from wiping her own tears. The Tin Woodswoman is the worst offender as mentioned earlier. She is literally paralyzed by sadness since her own tears cause her joints to rust shut. Theodore is constantly drying her eyes with a sleeve or a towel.

And Theodore cries most of all. Any young child would cry separated from their parents in a strange land filled with threatening magic and talking creatures. But how much is too much for a boy versus a girl? During their journey, Theodore would sometimes “cry bitterly for hours.” And he doesn’t just cry. He weeps when the Witch of Oz won’t send him back to Kansas right away. He sobs when he is told he’ll have to get used to living in Oz. And in what seems like a reprimand, he is told by the pretty green boy-servant to be careful that his tears don’t stain the fancy silk robe he borrowed. All these wet tears makes our hero appear much younger than he actually is.

When A Kiss Isn’t Just A Kiss

And lastly, I learned that even the most innocent of kisses appears suspect when gender roles are reversed. A peck on a little girl’s face from a motherly figure, even a benign stranger, feels so natural that it almost goes unnoticed in this story. But when Theodore is kissed by the North and South Wizards, there’s a twinge of inappropriateness, an awkward discomfort. Should a strange man in an authoritative position kiss a small boy?

We accept politicians kissing babies, but we also think of priests kissing alter boys. The world of woman is almost bereft of pedophiles and sexual predators, but the world of men is rife with aberration. Is it guilt that makes us uncomfortable? Is it so wrong for Theodore‘s Uncle Ed to “cover his face in kisses” when he returns from Oz? Is it strange that the Wizard of the North bends down and kisses Theodore on the forehead, leaving a protective mark? Is it queer for Theodore to kiss the little green boy-servant when they leave the Oz castle? Is it odd for him to beg a little porcelain prince to come home with him in his basket to be cherished? Theodore says, “You are so beautiful that I am sure I could love you dearly.” What is innocent and what is innuendo?

Even my own daughter suggested I might change some of these kisses to more benign hugs or handshakes. I was tempted, but in the end I wanted this dissonance. Originally the purpose of this experiment was to expose the gender biases of the 1900s. But in truth it reflects the stereotypes of today and what constitutes accepted male and female behaviour, even from a very young age.

Jason Theodor
February, 2015

The Wonderful Witch of Oz adapted by Jason Theodor

How will you react to a gender-swapped version of L. Frank Baum’s children’s classic? Get The Wonderful Witch of Oz on iBooks, Kindle, or as a PDF.

Jason Theodor is a creative director, writer, and public speaker who lives in Toronto, Canada. He sometimes blogs at, and works sporadically on his unpublished book, Create More Better Different, when he’s not chasing white rabbits.

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