Movie Review - She’s the Man (2006)

Country: United States

Language: English

Type of story: FtM Crossdressing

Is the protagonist Transgender? No.

Sexuality: Doesn’t change

Nudity: No

How I watched it: I watched it on Paramount+ (Watch Here). You can rent it from Amazon (Watch Here) 

When I last watched it: January 11, 2025

The next movie on my list to review was voted on by my Discord members.  Unlike many of the other movies I’ve reviewed, this one I’ve seen maybe a dozen times in the 18 years since it was made. I even used plot elements in it for crossdressing shenanigans in my story The Boy Who Would Be Prom Queen.

My synopsis (spoiler-free): Heavily inspired by Shakespear’s Twelfth Night, this is the tale of Viola (Amanda Bynes), who impersonates her twin brother Sebastian (James Kirk) in order to play for his school’s boy’s soccer team. While there, she befriends Duke Orsino (Channing Tatum) and Olivia (Laura Ramsey). In a perfect love triangle, Duke has a crush on Olivia, Olivia has a crush on Viola’s Sebastian (further known in this review as V-Sebastian), and Viola has a crush on Duke.  Both Duke and Olivia consult V-Sebastian for relationship advice. All of that and we still have that important soccer game coming up.

* * Spoilers ahead * *

There’s tons of backstory and a tangled web of relationships. Viola and her friends go to Cornwall. In the beginning she breaks up with her boyfriend Justin because he didn’t stick up for her. Coincidently Cornwall and Illyria are rivals.  As are soccer stars Duke and Justin. Predictably Cornwall and Ilyriawill be playing each other at the end of the movie. Sebastian’s ex-girlfriend-in-denial, Monique, keeps showing up to be a foil. Suckup student, Malcolm, also has a crush on Olivia and is out to get V-Sebastian for interfering. In addition to all of this, tomboy Viola is in Junior League, at her mom’s insistence, and now has to live both lives. Then the real Sebastian comes home early, confusing everyone! 

The transformation: Viola enlists her friend and stylist Paul (Jonathan Sadowski) to transform her into her brother.  We’re treated to a montage of Viola and her friends playing with a mustache, and Viola mimicking random male strangers.

V-Sebastian’s big reveal is when Paul drives him to Illyria and he steps out of the car. He’s a shorter version of the real Sebastian, but with the wig, fake eyebrows and sideburns, a boy's uniform, and lack of makeup, he is able to pass as a young teen boy (even though the real Sebastian is a senior). Duke and his friends ask V-Sebastian how old he is. He responds that he skipped a couple grades.

We see Viola change multiple times in the movie - mostly in the carnival scene when she’s constantly switching back and forth.

Does this Movie pass the Bechdel test? Barely - but that’s only because Viola doesn’t interact with other female characters often. She (either as herself or as V-Sebastian) interacts with her mom, Sebastian’s girlfriend Monique, Olivia, Eunice, and her two friends Kia and Yvonne. The only time she doesn’t talk about male characters is when she’s talking about soccer or the upcoming Stratford Junior League Cotillion.

Gender and Sexuality: The movie has a basic premise that girls can play boy’s soccer.  The Cornwall coach and Viola’s about-to-be ex-boyfriend scoff at the notion; and while V-Sebastian doesn’t make the first cut, he eventually does make the team. At the end of the movie, the Illyria coach announces that at Illyria they don’t discriminate based on gender. There’s no epiphany or sexual awakening for Viola. We never even get a same-sex kiss. And this is a movie that has a literal kissing booth in it! That’s because homosexuality is played off as weird in this movie.  Whenever V-Sebastian gets touchy with a guy, other guys get creeped out. As if being gay is the worst thing possible. With that being said, Viola and Olivia have some good onscreen chemistry even if they never follow through with it.  There are plenty of fans of the movie that think Viola and Olivia should’ve been a couple at the end.

How it ends: The charade is starting to catch up with Viola. The real Sebastian shows up, and Olivia, in a moment of truth, mistakes him for V-Sebastian, kisses him, and recites his music lyrics.  Duke observes them kissing and also mistakes Sebastian for Viola’s copy.  Now Duke hates V-Sebastian, thinking he stole Olivia from him. Duke kicks V-Sebastian out of their room, still unaware that it is really Viola.  V-Sebastian runs into Eunice, who gives him a place to sleep for the night, and breakfast in the morning.

The next morning is the day of the big soccer game.  The team mistakes the real Sebastian for V-Sebastian and sends him to the locker room to get ready. Meanwhile, V-Sebastian oversleeps in Eunice's room, and shows up at the game after her brother has already gone out to play. 

The real Sebastian sucks at soccer. Meanwhile, Malcolm and Monique - with Principal Gold in tow - are out to expose the whole charade. What they don’t realize is that the Sebastian playing soccer is the real Sebastian. Malcolm demands Sebastian prove he is a boy, so he drops his drawers for the crowd.

The game resumes, but Sebastian is benched for his poor play (it’s only his first game).  At halftime, Viola and Sebastian swap clothing.  V-Sebastian begs to be put back into the game. The coach reluctantly agrees.

Duke is still pissed and it's affecting his game.  A fight ensues between Duke and Viola’s ex-boyfriend, Justin. Everyone rushes the field.  Eventually Viola breaks down and tells Duke the truth. He is at first confused, then skeptical. Apparently they need proof even though Dude saw Viola at the carnival and kissed her at the kissing booth.  Like her brother, she gives the crowd a show and flashes her boobs to everyone.  The Hastings parents must be proud of their son and daughter.

Now that everyone knows what’s under Viola’s shirt, the asshole Cornwall coach from the beginning objects to a girl playing on the same field with boys.  He holds up a “manual,” which is promptly ripped up by the Illyria coach, who then vouches for her and lets her continue playing. Illyria wins off of Viola’s penalty kick.

Viola then introduces Olivia to the real Sebastian. Then there’s the cotillion. Eventually Duke forgives Viola and they start dating. Everyone has a happy ever after and nobody is going to need gender therapy.

Random Notes:  

• Everything about this movie oozes 2006. WIth its rocking soundtrack and bright colors, this movie is a welcome form of nostalgia.

• “You’re already better than half the guys” - Justin while flirting with Viola. Of course, in front of the boys and his coach he denies he said it.

• It appears as if the Cornwall soccer coach was also the girls’ coach as well.  If so, he’s an even bigger ass treating his now-former players like that.

• In the beginning Viola wearing a hoodie fools Monique into thinking she’s Sebastian -  “You’re scary alike.”

• So, Sebastian got kicked out of Cornwall for reasons unknown. He’s about to enroll in Illyria and instead flies to London with his band.  If not for Viola’s plan, Sebastian would’ve likely been kicked out of Illyria too.

• Viola drops tampons in front of Duke, Toby, and Andrew. Viola quickly says she uses them for chronic nosebleeds.  The three guys think that’s gross, but later in the movie Duke uses a tampon to stop his bloody nose after the carnival fight with Justin.

• Viola had two moments where people wanted her to remove her shirt. First was during soccer tryouts. Shirts vs. Skins.  Then later that night when the soccer team was hazing the new members. She was able to avoid both. 

• After Viola was ready to quit because she was a social outcast, Paul orchestrated a scene at Cesario’s, the pizza place,  where Kia and Yvonne were all over V-Sebastian. Then real Sebastian’s girlfriend, Monique, shows up unexpectedly. V-Sebastian demonstrates his moxie over women and the guys are now looking to him for relationship advice.

• When Viola became Olivia’s lab partner, Sebastian's music lyrics fell on the floor for Olivia to see.  Why did Viola even have those? Perhaps she was using Sebastian’s real backpack and those were in there.

• “Ask me about Cheese” Viola as Sebastian coaches Duke on how to talk to women. She suggests asking about her favorite cheese. Later Duke asks Olivia and she scoffs at the question. He also asks Eunice who LOVES cheese. As a peace offering, Viola gifts Duke a wheel of gouda and an invitation to be her escort at the cotillion.

• The Carnival scene is a classic and was an inspiration for my own carnival scene in The Boy Who Would Be Prom Queen.

• After the carnival, things are tense between Viola and Olivia.  That is until Olivia tells Viola (who’s herself at the moment) the truth.  She’s in love with Sebastian. She starts talking about him, making Viola blush. What’s odd is Viola tells Olivia to tell “Sebastian” the truth. She has to know that she’s directly telling her to hit on her again, right?  Good thing the real Sebastian shows up, right? Wouldn’t want Viola to turn gay or something, right? Someone give me some Viola/Olivia shipping fanfiction.

• In previous viewings, I wasn’t sure why the team took Sebastian to the game.  I realize now that Duke woke up still pissed about Sebastian and Olivia kissing and didn’t bother to wake him up on his way out.  Andrew and Toby later barge in yelling, “You’re going to be late!” and drag his confused ass to the game.

• Principal Gold (David Cross) is hilarious. He takes an interest in Sebastian because he too was a transfer student.  He’s always checking up on Viola at the wrong time. Like when Viola is adjusting her wig.  Principal Gold just assumes Sebastian is going bald - like him! Another time, Viola is walking by talking to her mom about the cotillion, and the principal overhears her talking about running in heels. He queries Malcolm, “Have you ever tried running in heels?”

• So apparently Amanda Bynes experienced gender dysphoria during filming watching herself play a male. She said it caused all sorts of self-esteem and body-image issues.

• Did anyone notice Paul (the stylist) was flirting with Andrew (one of Duke’s soccer friends) at the cotillion?

• We see Viola playing soccer as herself a few times in this movie, and neither time is her hair in a ponytail (except during the opening montage).  Her extremely long hair is flowing in the wind and getting in her face. Professional women soccer players either have short hair or tie their hair up.

• Potential Plot hole: Does Viola ever call out sick to explain her weeks-long absence?

• At the end of the movie, we see Viola continuing to play soccer for the Illyria Boys Soccer team as herself. Sure, she made the team, but, is she allowed to be a member of that despite that she doesn’t even go there? She’s still a Cornwall student? Maybe she transferred. Afterall, her brother goes to Illyria now.  So does Duke and Olivia.  The only friends of Viola still at Cornwall are Kia and Yvonne.

Real world politics: Conservative United States Lawmakers must’ve gotten their genital check idea from the soccer match scenes. Both Sebastian and Viola have to show THE ENTIRE STADIUM their private parts.  Republican lawmakers are jerking off reading this very paragraph. I should review Ladybugs (1992) next to show everyone what conservatives THINK is happening to girls sports in the United States.

Comparison to Just One of the Guys (1985): I did a review on Just One of the Guys here. Two movies, similar plots, twenty one years apart. Two girls who are just trying to prove that they are just as good as boys crossdress as a boy at a new school. Both fail at first then succeed, both fall in love with their friend. Neither wind up trans. Nobody gets gender therapy.

Twelfth Night: You can see how similar this movie is to the 17th century Shakespearean comedy. In the play, Viola is shipwrecked on the shore of Illyria. She has lost contact with her twin brother Sebastian. She disguises herself as a male named Cesario. Cesario comes to work for Duke Orsino.  Orsino is in love with Olivia who is in mourning and won’t see any men. Orsino uses Cesario as an intermediary to profess his love. Naturally, Olivia falls in love with Cesario instead and Viola falls in love with Orsino to complete the love triangle. Of course Sebastian eventually shows up and the twins are confused for each other. The names Andrew, Toby, and Malvolio are also reused.

Overall impression: It’s a fun comedy. There’s no doubt about that.  The crossdressing feels real. Amanda Bynes is funny as Viola. Her Sebastian is kinda cringy at times when she’s trying to be a toxic macho man.  But when she tones that down later in the movie, she’s charming.

But the movie doesn’t go far enough, and there’s too much 1990’s gay humor (and this was 2006!).  It certainly has its problems that haven’t aged well.  Paul is reduced to a token gay hairdresser stereotype. The soccer guys freak out at minor intimacy between guys. Viola and Olivia should’ve kissed at least once. Hell, Viola should’ve kissed Duke while in full-blown V-Sebastian mode.  And the kicker? One of the last lines of the movie was by Duke “It’d be a lot easier if you stayed a girl.” Maybe that was innocent in 2006. But in 2025? YIKES.

At the end of the day it was a crossdressing movie, not a transgender movie.  If it was a transgender movie, most likely it wouldn’t have gotten made.  When it was made, it sparked outrage from conservative mom’s groups for encouraging crossdressing and being queer.