A Trans Guy Watches ‘She’s the Man’ for the First Time

I avoided the 2006 teen comedy She’s the Man for almost two decades. I know this Amanda Bynes/Channing Tatum comedy is really important to a lot of trans guys, but somehow even before realizing I was trans, I felt a panicked aversion to it.

It’s no surprise it’s part of the trans canon: She’s the Man is about a tomboy who cross-dresses so she can pass as her twin brother and play for a men’s high school soccer team. Shenanigans ensue.

In March 2006, when this movie came out, I was about two months shy of graduating from a religious high school in Florida. I was out to myself as bisexual, but I knew absolutely nothing about trans men. I’d seen all the other Shakespearean adaptation teen movies – 10 Things I Hate About You, Get Over It, O. But I very deliberately never watched She’s the Man. I think subconsciously I was worried about the feelings it might bring up for me. Bynes, in an interview with Insider in 2018, described experiencing gender dysphoria when she saw herself as a boy on screen. I knew she’d had this experience, and it delayed my first watch even longer.

But now that Amanda Bynes in drag can no longer turn me trans — watching HBO’s Looking during lockdown did that — I figured it was finally time I watch this movie. Here are my thoughts.

1. Viola Hastings is an incredible character played by a comedic genius.

Bynes’ Viola seamlessly balances masculine and feminine energies. She’s no shrinking violet who needs to learn how to become a tough guy. And there’s no overwrought explanation or tragic backstory as to why Viola isn’t a girly girl. She’s a confident and sexually frank character, even if she might just be a straight cis woman who plays sports.

Viola doesn’t need her mother’s approval on her gender presentation. When her mom tries to talk her into wearing a pink debutante dress, it gave me But I’m A Cheerleader vibes. Amanda’s fearless physical comedy felt appropriately like a mix between Natasha Lyonne’s femme Megan and Clea Duvall’s masc Graham.

While prepping for her female-to-male transformation, Viola follows men around on the street to imitate their walks. She’s never worried about if her behavior is going to be unattractive to the men, or garner negative, scary attention. She simply isn’t deferring or referring to them at all.

Because this isn’t a “trans film,” trying different gender presentations is allowed to be just chill girly things. I loved the upbeat “girls trying on mustaches” montage after Viola decides to go undercover as her brother. It’s cute and fun and she makes it feminine. It stands out against the usual “trans person staring at themselves in the mirror” moment in most trans films.

While Viola is masquerading as her brother Sebastian, she’s not worried that Duke won’t find her hot, just that she won’t be able to get with him in her current form. It’s not, “Does this boy like me?” It’s, “Do I like this boy more than I want to keep playing soccer?” And that’s a level of confidence I don’t have even a year and a half on T.

2. The dean is a trans man.

The one canonically queer character is Paul, the hairdresser that helps Viola transform into a man. At the very end of the movie, he’s seen at the debutante ball, flirting with Duke’s friend Andrew, who seems into his attention.

My “change my mind” take is that their school dean, played by David Cross in a bow tie, is a trans man.

In his first scene, he tells Sebastian-Viola that he’s a fellow “transfer student” who looks out for other transfer students. I don’t think the filmmakers meant it as a code for anything queer but it did bump for me when looking at this movie through a trans lens. David Cross also commiserates with Sebastian-Viola about going bald and later, alludes to having worn high heels in the past. A “trans”-fer student, indeed.

3. This movie was not as gay as I’d been led to believe.

I was under the impression that Tatum’s Duke was canonically bisexual or at least wink-wink bisexual. But there’s no attraction to Sebastian that makes Duke question his sexuality even if you’d all led me to legit believe that was the plot. It was probably a big ask for a mainstream movie in the 00s, but I was expecting at least some kissing while Viola was in Sebastian drag.

There’s a little lesbianism when Kia and Yvonne show up to make Sebastian-Viola look like a ladies man, and Bynes gamely and enthusiastically slaps Yvonne’s ass. I also thought she’d have to kiss Olivia when presenting as Sebastian but the movie didn’t go there either.

It’s not enough that I’m robbed of a single gay smooch in this movie, but Viola is also hounded by her mother to participate in a carnival kissing booth. The girl prior, which happens to be a struggling-to-kiss-men Olivia, has kissed 350 people by the time Viola relieves her. She warns Viola that the elderly man in line kisses with a lot of tongue. Really??

After all that, at least let Sebastian-Viola kiss Duke and Olivia!! Straight people are ridiculous.

Then, the final soccer game presented some pretty stark gay and trans panic from our guy Duke. The part where Viola was outed in front of the whole school and her parents was hard for me to stomach, even if it wasn’t really a trans outing. Dean David Cross announces via megaphone that “Sebastian is a girl.” He literally shouts, “Sebastian Hastings is a girl!!” I imagined a teacher doing this to an actual trans student today, and it was hard to see it as comedy in the current climate.

The Dean also explains that Viola is going to need “extensive psychoanalysis.” The real Sebastian then has to pull down his pants and show his penis to prove he’s a boy. A literal children’s sports genital check, which was so outlandish then that it was fodder for jokes.

When Viola as Sebastian finally tells Duke, in front of everyone, that she loves him. His face is pure disgust. Before he realizes Sebastian is really Viola, he’s giving old school violent homophobia. And when Viola says they kissed, he is quick to make sure the team knows he didn’t kiss Sebastian! Because he was NOT kissing a dude! Even when she reveals herself to be a woman, he’s still visibly grossed out. (Or maybe he just feels betrayed? They never really explain what’s going on for him mentally and emotionally here.)

Wasn’t the selling point of this movie that there wasn’t any gay panic and that Channing got confused by having bisexual feelings? (Whether they turned out to be real or not.) I thought queer people liked this movie because one of the plotlines was that Channing Tatum was into boy-Amanda, and was confused about why. More of a Mulan situation, less of a Boys Don’t Cry. Did I Mandela Effect this?

4. The trans feelings did come up for me just like I thought they would.

When gay Paul drops Sebastian-Viola at school, he tells her that “inside every girl, there’s a boy” (hot) and also tells her to “be a good boy” (extremely hot). But I can’t help but think about the current trans grooming panic. A gay man telling a teenage girl that there’s a boy inside her and inside every girl (even without the innuendo) is bold gender exploration. It makes the kissing booth stuff even more depressing by comparison.

There were definitely a lot of scenes that did exactly what I was worried they would: They made me feel not so good about my body. Seeing Sebastian-Viola when he is first next to the cis men at his new school was like being slapped in the face with a cold fish.

Is that what I look like next to my cis guy friends?

This is the question that has kept me away from this movie for so long. The joke is: Sebastian-Viola looks so obviously different from the other boys. Is that how the cis men in my life perceive me?

It’s hard to tell where the movie even stands on this. When Sebastian-Viola arrives at the Illyria school, she imagines everyone in the hall is staring at her because she doesn’t pass when in my interpretation, it was probably either because she was new or because she looked hot. (A common trans anxiety: Are they staring? Why are they staring? Is it good or bad? Good or bad?!) It’s never explained because maybe as a gender expansive person, we can never really know.

There’s a lot that’s relatable: She’s immediately told she looks young. She hates the rowdy hallway of her men’s dorm similarly to how I’ve had a hard time dealing with gross men’s bathrooms. She struggles to find private time to shower or remove her ACE bandage binder. Her coach uses homophobic insults like “nancy boy.” And one night, Viola has a nightmare where the boys mock her because she’s wearing the pink debutante dress her mother wants her to wear.

5. That reconciliation scene is the final trans guy gut punch.

The relationship between Viola and Duke only recovers from the soccer game where he was repulsed by her, and gets tender again at the very end when they meet by the lake. Viola has set up Olivia and real Sebastian as though replacing the girl version with the boy version makes Olivia’s experience any less queer. And Duke has come to the debutante ball to win Viola back and usher her into polite society as a straight cis woman.

“Maybe if I’d have known you were a girl,” Duke says, “we would have never talked the way we did and got to know each other the same way and that would have been a shame.”

It’s pulling at my closeted trans guy heartstrings, because the next words he says are, “Everything would be a lot easier if you stayed a girl.” And she says, “I promise.”

That’s how Viola gets the happy ending. By promising to stay a girl. A thing not a single one of us can promise a partner.

But if the film’s dilemma is whether or not Viola can reveal she is really a girl, so maybe Duke would choose her, is She’s the Man closer to being about the trans girl experience than it is about the trans guy experience? Maybe we’ve had this all wrong. Maybe all the movies about girls cross-dressing as boys are really for the girls and all the movies about boys cross-dressing as girls are for the boys. Or maybe there’s a little something here for all of us.

I’m glad I finally ripped the bandaid off watching this film for Bynes’ performance alone, and I’m happy for any queers for whom this movie brought solace and joy. It’s a very solid, very funny teen comedy. I’m just glad I didn’t see it in high school – even if I would have had a bisexual crush on Amanda Bynes in drag.

She’s the Man is now available to rent.

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  1. I haven’t seen the movie, though I’ve been interested in reading this and other trans analyses of it. Originally I would have said I was probably just too old when it came out, but your article made me think about how this is a twisted version of the “girl disguised as a boy” trope that I otherwise LOVED as a kid (and adult) for very genderqueer reasons. I think the reason even the trailer made me cringe was that not only was the movie a comedy (often not my favorite genre tbh), but the extent that her dressing as a boy was the focus of the jokes. It definitely kills the wishfulfilment element these stories usually had for me–which honestly largely mirrored my real-life experience that gender was a lot less obvious and binary and a lot more fluid/permeable than people tend to assume.

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