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By Robert Scucci
| Published

Have you ever seen an 80s romantic comedy fantasy film for teenagers that is as problematic as it is progressive? Well, if you haven’t, then you need to check out 1986’s Willy Milly. If you’ve never heard of this title, then you might want to check out its alternate titles, I was a Teenage Boy a Something Specialbut also know that you can stream right now Willy Milly free on The Roku Channel at the time of this writing.
There’s a lot to unpack here, so we might as well get into it.

Willy Milly focus on Milly Niceman (Pamela Adlon), a 14-year-old tomboy 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 because she thinks being a boy is much easier than being a girl.
Everything changes for Milly when the eccentric younger brother of her best friend Stephanie (Mary Tanner Bailey), Malcolm (portrayed by a very young boy). Green Seth in one of his earliest roles), sells her a magical charm that will grant her a wish in the form of her deepest, darkest desires coming true if she follows his specific instructions during the upcoming solar eclipse. As it turns out, Milly’s deepest, darkest desire is to become a boy, which manifests physically in the form of male genitalia under her gown the next night when she wakes up.
Much to the displeasure of her mother, Doris (Patty Duke), Milly decides to change her name to Willy and live as a boy, which at first upsets her father. That is, until he realizes he finally has the son he always wanted. Realizing that it would be impossible to explain that Willy used to be a girl called Milly, Fred arranges for his son to be transferred to a new school so that he can have a fresh start after his transformation.
Unfortunately for Willy, he learns that being a boy has its own difficulties as he tries to navigate teenage life with his new identity. Matters continue to get complicated in Willy Milly when Willy befriends a boy in a wheelchair called Alfie (Eric Gurry), who feels conflicted because of his attraction to Willy, who used to be a girl a week earlier.

Given that Willy Milly saw a release in 1986, I have to say that it was actually quite ahead of its time, socially speaking. When Milly transforms into Willy, Fred does everything he can to make sure his son feels comfortable in his new body. Although Fred pushes a little too hard on the gender norms he is familiar with as a man approaching middle age in the 1980s, such as teaching Willy how to box and swear so he can be the alpha male, quickly learning to appreciate Willy for who he is. and wanted to be, never referring to him as “she” after his transformation, and making several misguided but well-intentioned attempts to ensure that his ex-daughter felt she was seen as his son after deciding to live life as a boy
However, while Fred was supportive of his son’s transition in Willy Millyhe still sees the world through the lens of what today would be considered a prime example of toxic masculinity. You have to give Fred credit for doing his best given the circumstances, but Willy Milly unable to catch up in today’s coverage by the time it reaches its third act when Alfie professes his love for Willy and feels tremendous shame for his feelings.
What’s more, you may find the typical teenager sex comedy beats within this context to be a little on the creepy side. After all, Alfie and his fellow nerd friends have a secret junkie spot where they hide from bullies and try to hook up with girls despite the fact that they have no game on the romantic front. I found myself cringing whenever Willy went on his swearing tirades in an attempt to come off as sexually experienced because it’s very easy to misinterpret the conversation in the locker room as being incredibly overbearing and borderline at times.


Willy Milly is one of those films that you have to appreciate for being so ambitious, but which fully deserves criticism for not fully committing to the piece. On the one hand, it tackles some of the gender issues we face today in a way that can make those struggling with their own gender identity feel like they are be seen and heard. But for every bit of progressive discourse (intentional or not) found in it Willy Millyultimately it fails to stay grounded because of how hard it veers into the stereotypical gender norms that were so common in past decades.
If you’re willing to go on an adventure that’s equal parts wholesome and exhausting, you can stream Willy Milly free on The Roku Channel as of this writing. And if you want to dive even deeper into the film, you can look at the GenreVision podcast for more insight and observations.
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