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Have you ever seen an 80s teen romantic comedy that’s as problematic as it is progressive? Well, if not, then you need to check out 1986 Willy Milly. If you’ve never heard of this title, you might want to check out its alternate titles, I was a teenage boy and Something specialbut also knowing that you can currently stream Willy Milly free on the Roku channel at the time of writing.
There’s a lot to unpack, so let’s get straight to it.
The “grass is always greener” scenario.
Willy Milly centers on Milly Niceman (Pamela Adlon), a 14-year-old girl who is obsessed with astronomy. Knowing that her father Fred (John Glover) always wanted a son and not a daughter, Milly is frustrated with her place in life, thinking that being a boy is much easier than being a girl.
Everything changes for Milly when her best friend Stephanie’s (Mary Tanner Bailey) eccentric younger brother Malcolm (played by a very young Seth Green in one of his earliest roles), he sells her a magical spell that will grant her a wish in the form of fulfilling her deepest and darkest desires if she follows his specific instructions during the upcoming solar eclipse. As it turns out, Milly’s deepest and darkest desire is to become a boy, which manifests physically the next day when she wakes up in the form of male genitalia under her nightgown.
Much to the displeasure of her mother, Doris (Patty Duke), Milly decides to change her name to Willy and live as a boy, which initially upsets her father. That is, until he realizes that he finally has the son he’s always wanted. Realizing that it would be impossible to explain that Willy used to be a girl named Milly, Fred arranges for his son to transfer to a new school so he can start over after the transformation.
Unfortunately for Willy, he discovers that being a boy has its own difficulties as he tries to navigate teenage life with his new identity. Things keep getting complicated Willy Milly when Willy befriends a wheelchair-bound boy named Alfie (Eric Gurry) who feels conflicted about his attraction to Willy, who until a week ago used to be a girl.
A surprisingly progressive but unfortunate product of its time
Given that Willy Milly I saw the release in 1986, I have to say it was actually quite ahead of its time, socially speaking. When Milly transforms into Willy, Fred does everything to make his son feel comfortable in his new body. Although Fred leans a little too hard on the gender norms he knows as a middle-aged man in the 1980s, such as teaching Willy to box and scold so he can be the alpha male, he quickly learns to appreciate Willy for who he is . and wants to be, never referring to him as a “she” after his transition and making several misguided but well-intentioned attempts to make sure his ex-daughter feels like his son after he decides to live life as a boy .
However, while Fred supports his son’s transition inward Willy Millyhe still sees the world through the lens of what today would be considered a blatant example of toxic masculinity. You have to give Fred credit for doing his best under the circumstances, but Willy Milly it doesn’t stand up to scrutiny today when it reaches its third act, when Alfie confesses his love for Willy and feels immense shame for his feelings.
What’s more, you can find the typical teenager sex comedy beats being a little creepy in this context. After all, Alfie and his fellow moron friends have a secret junkyard location where they hide from bullies and try to hook up with girls despite the fact that they have absolutely no game on the romantic front. I found myself cringing whenever Willy continued his swearing in an attempt to appear sexually experienced, as locker room talk can easily be misconstrued as incredibly forced and sometimes borderline misogynistic.
One of the movies of all time
Willy Milly is one of those movies that you have to appreciate for being so ambitious, but totally deserves criticism for not fully committing to it. On the one hand, it addresses some of the gender issues we face today in a way that makes those struggling with their own sexual identity feel seen and heard. But for every bit of progressive discourse (intentional or not) found in Willy Millyultimately fails to hold the landing because of how hard it leans on the stereotypical gender norms that have been so prevalent in past decades.
If you’re willing to embark on an adventure that’s equal parts wholesome and raunchy, you can stream Willy Milly at the time of writing for free on the Roku channel. And if you want to dive even deeper into the movie, you can check out the GenreVision podcast for more information and observations.
