Willy/Milly (And Other Gender-Bending Films)

Watch.

Available Summary:

When 14-year-old Milly Niceman wishes that she was a boy instead of a girl, her wish comes true overnight and she develops a new persona as a boy named Willy.

-Filmpedia.

Initially released as I Was a Teenage Boy in 1986, the film was later re-titled to Something Special for a 1987 limited theatrical release and for a VHS release.

-Wikipedia.

Jack's Analysis:

Willy/Milly is not a trans film in the traditional sense, and can instead be considered a film about a tomboy; certainly, I believe that it was intended to be interpreted in the latter way. Regardless, it is important to discuss when considering the media history of female-born gender non-conformity and masculinity.

This film is very similar to Just One of the Guys (1985), but with magic added into the mix. And, much like Young Americans (2000), it depicts a female-to-male change which deeply disturbs a cishet guy, who is confused about why he is attracted to the male-presenting protagonist. The message, essentially, is that male love interests can tell that the guy they're looking at is not a "real" guy, due to their heterosexual radar subconsciously picking up on the protagonists' birth sex, leaving them fearing that they are gay. Another example of this can be seen in the homophobic film 金枝玉葉 (1994), also released as He's a Woman, She's a Man, where the male love interest enters a crisis, panicking about his sexuality.

In all four of these examples, concern is alleviated by the end, when the male-presenting protagonists reveal that they are actually girls. The male love interests are able to banish any thought of being attracted to guys, relieved that they're not truly gay. Or bisexual. Perish the thought!

In all four examples, the reason male-presenting protagonists resume living as girls is because they are attracted to their male love interests. The queerness of presenting as a male is resolved by a staunchly heterosexual, cisgender, guy-meets-girl happy ending.

Another thing which all of these films share is unwelcome sexual attention from girls and women. In Willy/Milly, Willy is pressured to be intimate with a girl named Cynthia, but is not assaulted by her. In Just One of the Guys, the male-presenting protagonist is sexually assaulted when a girl gropes inside his pants. In Young Americans, the male-presenting protagonist is kissed without consent by a girl (and he kisses his love interest without consent as well). In He's a Woman, She's a Man, the male-presenting protagonist literally runs away from a woman who is trying to pressure him into sex, saying no multiple times as she tries to force him into intimacy. In Our Flag Means Death, a male-presenting non-binary character is backed into a corner by a woman who is making unwanted sexual comments, with the harassment intended to be funny.

This key theme in AFAB crossdressing and gender-bending media asserts that the sexual harassment of boys/men is hilarious, and the male-presenting protagonists are asking for it due to their non-normative appearances. This is consistent with the larger issue of sexual assault against men being depicted as comedy, with transphobia as the cherry on top; the joke, often, is that these male-presenting protagonists have a dirty secret (their birth sex) which risks being discovered if they are groped. This is a very old trans trope, also seen in I Want What I Want (1972), in which the trans female protagonist is sexually assaulted and therefore outed as a trans woman.

When Willy/Milly begins, viewers are introduced to Milly; ostensibly a tomboy who wishes to experience the freedom and respect which boys enjoy. This desire to be a boy is so profound, however, that when Steph's younger brother offers instructions to perform a magical ritual which will grant a person's deepest desire, Milly takes the opportunity.

(Side note... this ritual is a ridiculous approximation of so-called Indian magic, reminding viewers that this, unfortunately, is an 80s film...)

Milly wishes to be a boy and, later that night, wakes up to find a penis and a flat chest where previously there were only breasts and a vulva. Milly, while initially shocked, wishes to keep this new body rather than seeking to reverse the magic.

After Milly's parents discover that their child has a penis, they have Milly medically examined. The practitioners tell them, "Your little girl is both a little girl and a little boy. She has both sexes right inside her," suggesting that Milly has an intersex genital variation which went unnoticed until age fourteen. Milly's mother asks what to do, and one of the doctors says, "Well, she must make a choice." In response, Milly incredulously asks, "Can't I be both?"

Milly's parents do not know about the magical ritual that Milly performed. They simply think that their child is intersex, as do the doctors. Because of this, Willy/Milly stumbles into clumsily representing intersex people.

Like many individuals with innate sex differences, Milly is immediately pressured to choose maleness or femaleness, with society and the medical establishment viewing Milly's body as a problem to be corrected. The very fact that Milly's sex differences immediately necessitate interrogating Milly's gender is, in itself, anti-intersex bigotry.

Supposing that Milly had been born an intersex woman whose variations were discovered years after birth, those variations would not make her any less of a woman, if that were her identity. Any gender exploration would be Milly's to pursue at her leisure, if she ever even felt the need. Furthermore, intersex diversity is not inherently a problem. Medical interventions should only ever occur if health or life is at risk, or the intersex person themself chooses to pursue interventions, without being pressured or coerced by others.

The difference in Willy/Milly, of course, is that the protagonist has deliberately sought out genital variations as an expression of preference. These differences are acquired (trans) rather than innate (intersex), though Milly's parents don't know that.

Milly's parents panic and argue about how Milly should live. Milly expresses a preference to live as a boy, but does not necessarily desire a binary life. He wants to present as a boy and move through the world as a male, but says that he will still be a girl inside, to whatever degree. This, Milly tells his mother, can be their "secret". Milly wants to explore gender, not be boxed in.

This gender ambiguity angers his father, who says, "There will be no grey in this house. For fourteen years, we thought you were a girl. That's okay, it's alright, anybody could make a mistake. And now, you're telling us that you want to be a boy... And you want to be a girl, too?" He later adds, "No, no, no. There will be no girlish boys in this family! You make your decision, and you abide by it! Black or white. Boy or girl."

That night, sitting with his best friend, Willy looks up at the moon and says, "Oh god, Steph... It's like, there's this whole other side of me that I've never seen. Do you think I should do it? I mean... Try it out, at least?"

For a comedy movie, Willy's gender exploration is oddly earnest, to the point that it's almost out of place. Unlike other AFAB gender-bending films, Willy has no defined goal when choosing to present as a boy. In Just One of the Guys, Terri/Terry goes undercover to investigate sexism in the schooling system. In Young Americans, Jaqueline/Jake is male-presenting to see get her mother's attention, and to see what she can away with behind her mother's back. In He's a Woman, She's a Man, Wing presents as a male to meet her idols. In Our Flag Means Death, Jim is disguised to hide their true identity, because they are on the run.

By contrast, Willy chooses to live as a boy because... he just wants to. And, when he does make this decision, he smiles widely and seems genuinely happy. This framing makes Willy/Milly more of a trans film than I expected, as does the scene where Willy's parents are sitting at the kitchen table, discussing how they will navigate the neighbourhood's response to their child's new gender presentation. Doris, Willy's mother, fretfully suggests, "Maybe we should move." Fred, Willy's father, dismisses that idea; "We just take it one step at a time, and then there will be no problem. I'm telling you, Doris, I had to pull a few strings to get this new high school to accept him." Fred pointedly emphasises the unfamiliar pronoun.

While Willy seems self-conscious about his new appearance for a short time, or perhaps just overwhelmed, he commits to his preference to live as a boy. His parents, waiting at the table, are shocked into silence by his masculine appearance. Fred says, "Morning... son," and Willy smiles at his father's words.

Fred, driving Willy to the high school where he has been newly enrolled as a boy, says, "It'll be a fresh start. New school, and all. You're my boy, right? Willy Niceman." Willy beams at being addressed this way. He is also thrilled when Fred gives him a stopwatch which originally belonged to Willy's grandfather, passing it down to the next son.

Now, I am absolutely aware that much of this gender ambiguity and trans identification may have been intended as a joke, and it is only in retrospect that Willy perhaps seems like a genuine trans character. Certainly, the hijinks which ensue after Willy arrives at his new school do remind viewers that this film is intended to be a comedy, with a dash of social commentary on gender roles.

After Willy is punched in the face by a bully, Fred has very little sympathy, and Willy is shocked by the expectations of machismo he now faces. He is surprised by how differently he is treated when living as a boy, where he could expect tenderness and protectiveness whilst living as a girl. He was intimately familiar with the restrictive gender role of being a girl, and quickly learns that the restrictive gender role of being a boy has its own, very different, harms.

Fred insists that Willy must learn how to fight, instructs Willy to call him pops instead of daddy, and curse more. Willy is expected to embrace aggression, enforce dominance, suppress "weak" emotions, and uphold a stereotype of manliness; all of this, toxic masculinity. The film takes this to a satirical extreme, showing Willy catcalling women on the street, randomly yelling and cursing at home, and punching walls for fun. His mother is distressed by his behaviour, whereas Fred is delighted.

As the film proceeds, Willy settles into a normal boyhood despite Fred's best efforts to push him into harmful behaviours. He shows care and affection for his new friend Alfie, who uses a wheelchair, alongside friends who have modified a bus so that they can drive Alfie to-and-from school. When Alfie is targeted with an ableist slur by bullies, Willy stands up for him despite the likelihood of being targeted in retaliation. When Alfie jokingly asks Willy to "play the girl" during a flirtatious conversation, Willy does so, in contrast to the hyper-manly expectations of his father. He seems genuinely comfortable with his new friends.

Attraction to women is part and parcel with the hyper-manly, heteronormative role which Willy has been pushed into. As the film progresses though, it becomes clear that, while girls flirt with Willy and he does the same, he is not attracted to girls. He is attracted to boys. Specifically, he is attracted to Alfie.

Alfie, for his part, finds himself attracted to Willy as well. This sends him spiralling, causing an identity crisis as he worries that he is gay. He tells Willy that he has "unnatural desires," and calls himself a faggot. To be clear, Willy has a penis and a flat chest, and is socially male. Alfie is, in all respects and as far as he knows, attracted to a male.

Further hijinks, conflict with bullies, and pressure to be intimate with a girl ensues, all wrapped up by the central group of friends triumphing over their bullies. After the group's victory, Willy tells Alfie that he used to be a girl. Alfie doesn't believe him. So, Willy reunites with Stephanie, apologises for neglecting their friendship while living a new life as a boy, and uses magic to return his body to its original female sex so that he can be in a relationship with Alfie.

Milly arrives at a school dance, presenting femininely. Alfie is stunned, but is relieved to find out that his attraction to a male wasn't really attraction to a male, so it's all fine. He asks Milly out on a date, and the pair walk off together.

As occurs in Just One of the Guys, Young Americans, and He's a Woman, She's a Man, heterosexual romance ultimately triumphs over everything else. In those other three examples, however, all of the protagonists were male-presenting for personal gain or with a goal in mind, not as an expression of preference or identity. Even viewing this film as simply the fantastical journey of a tomboy girl, what would have been compelling (for me personally) would have been Milly retaining some of the masculinity she enjoyed embodying while living as Willy, ditching the hyper-manly silliness while incorporating parts of her exploratory boyhood into her female identity. After all, girls can be masculine. Girls can be tomboys without being trans. Milly did not need to cast off Willy entirely, even if embracing her female sex once more.

As previously stated, I don't think this film was intended as a trans movie specifically, or as a commentary on intersex experiences. I think that this film was simply intended to be a send-up of gender roles, gendered expectations, and sexism. It is still quite interesting to interpret through a different lens.

I originally found this film through Dagger: On Butch Women (1994), reproduced here by butchdotorg. The author, Jenni Olson, describes the film thusly:

In this obscure teen transgender comedy Milly Niceman wishes she were a boy and then wakes in the middle of the night to discover she's magically grown "a guy's thing down there." Her family and friends make the adjustment to her new male self, Willy, and the film plays extensively on all of the homo and lesbo-erotic potentials available. She goes back to being a girl at the end (so she can be with a boy), but she's still a butch girl even if she is straight.

This film can be interpreted in so many different ways and, as ever, I would never suggest my interpretation is the only correct one.

WARNING: Sexism and coercive actions.

Early in the film, Fred is kissing Doris in the kitchen, when he announces his intention to get her pregnant so that they can have another child. She literally runs away from him and he pursues her, undoing her apron and carrying her off to the bedroom against her will, so that they can have sex. She continues to argue with him as he carries her, because she doesn't want another child. This scene is intended to be comedic, I suppose, but it looks rather like an abusive marriage, even if portrayed as a joke.