How does a crossdressing feminist comedy from the 2000s, inspired by a Shakespeare play, hold up 20 years later? Speaking as a completely objective third-party observer with absolutely no personal interest in the matter … It’s brilliant. Shhh!
She’s the Man doesn’t shy away from its source material, keeping the original names and general plotline of Shakespeare’s “Twelfth Night.” Amanda Bynes delivers a masterclass in comedic commitment, playing the lead character, Viola, disguised as her twin brother, Sebastian (James Kirk), for two weeks at his boarding school to prove her capabilities as a woman on the soccer field.
Viola falls for Duke (Channing Tatum) while rooming with him and acting as his bro … brother … brethren? Duke sets his sights on Olivia (Laura Ramsey), who is instead newly enthralled by Viola in her Sebastian disguise, producing a love triangle that is delightfully queer-coded. Everything Olivia loves about this fake Sebastian is actually the traits of Viola in masculine clothing, from tenderheartedness to softer handsomeness. The sapphic allusions halt there, keeping the story aligned with the original Shakespearean text and concluding with Olivia and the real Sebastian paired up (to the dismay of many modern queer Letterboxd reviewers).
In a very Mulan (1998) trans subtext way, Duke and Viola develop feelings for each other throughout the film, despite Duke’s jock nature and confusion about the fake Sebastian’s chaotic personality. But again, the film doesn’t take it to that place beyond surface-level humor.
Revisiting this story in 2026, the playful simplicity still works. One wonders if the creation of a story like this in modern day would have darker undertones of “transvestigation” from conservative jock teammates. On the other hand, some moments, though entertaining, feel archaic in She’s the Man, such as Sebastian dropping his pants to prove he’s a man or Viola flashing her boobs to prove her womanhood.
Despite its murky gender exploration, the film’s clear goal (beyond producing laughter) is feminist. The inciting incident is Viola’s school cutting her soccer team and forbidding her and her female teammates from trying out for the men’s team. She dumps her boyfriend when he backs the coach’s decision. On a rewatch, it’s sad to see how the sneering sports misogyny is as relevant as ever in 2026, particularly calling to mind the recent Olympics scandal of the USA men’s hockey team laughing at President Trump’s tasteless joke about the women’s team.
However, one positive thing remains true in both this fictional narrative and in real life: women can achieve anything. Eight of the 12 Olympic gold medals awarded to Team USA during the recent Winter Olympics were won by female athletes. Alysa Liu stole our hearts on the global stage this year as she showed us that excelling does not require suffering. She returned from figure skating retirement on her own terms: setting boundaries, taking rests, and refusing to starve herself.
It’s invigorating to see women, not just in sports, push against the harsh conditions of living in the spotlight. Recently, watching Chappell Roan’s outspokenness on this topic and the backlash she receives, it begs the question: Have we learned nothing from the tragedies of Amy Winehouse, Britney Spears, or Selena?
Another woman weathered by the industry, our leading lady, Amanda Bynes, caught her big break at age ten, starring in “All That” (1994–2020), followed by “The Amanda Show” (1999–2002) on Nickelodeon. As she entered her teen years, she starred in the sitcom “What I Like About You” (2002–2006), along with the hit films such as What a Girl Wants (2003), Hairspray (2007), and Easy A (2010). All of this success from such a young age. But at what cost?
The seedy underbelly of Nickelodeon has more recently come to light, from the tell-all memoir “I’m Glad My Mom Died” by Jennette McCurdy to “Quiet on Set: The Dark Side of Kids TV” (2024). In her book, McCurdy reveals that she was offered a handsome sum of hush money to sign documents disabling her from speaking on her experience at Nickelodeon. Although she refused the funds, it may answer some questions regarding why other stars like Ariana Grande or Miranda Cosgrove don’t publicly discuss their experiences in detail. From the information we do have, one thing is for certain: Dan Schneider exhibits predatory behavior, and his TV sets were not the safe spaces they should’ve been for children.
Bynes has struggled with mental health and substance abuse issues, retiring from film and television after Easy A because she hated her appearance and her performance in it. When She’s the Man was released, and she finally saw it, she said she “went into a deep depression for 4-6 months because I didn’t like how I looked when I was a boy,” and that seeing herself with the short wig and sideburns was “a super strange and out-of-body experience. It just really put me into a funk.” Knowing the dysphoria she felt witnessing her own powerhouse performance adds a sad layer to the rewatching experience. She has no idea how much of a badass hunky dude we all find her to be.
In recent years, she’s hosted art shows and posted about upcoming music production projects. One can only hope that Bynes finds peace and growth despite the environment in which she grew up.
Although Hollyweird can be bleak, modern Shakespeare adaptations reinforce the timeless genius of the wordsmith’s body of work. From 10 Things I Hate About You (1999) as a reinvention of “The Taming of the Shrew,” to John Tucker Must Die (2006) retelling “The Merry Wives of Windsor,” to even The Lion King (1994) loosely following “Hamlet,” the playwright is everywhere you look. Not to mention the countless iterations of “Romeo and Juliet,” ranging from West Side Story (1961) to Gnomeo & Juliet (2011). They’re not all rom coms or musicals, as proven with the sci-fi film Ex Machina (2014) re-interpreting “The Tempest.” Whether through comedies of errors or dramatic tragedies, Shakespeare’s mark on society is undeniable.
In 2025, “Twelfth Night” underwent a modern star-studded revival on New York’s Delacorte Theater stage in Central Park, featuring Lupita Nyong’o as Viola, Sandra Oh as Olivia, and Peter Dinklage as Malvolio. It seems to act as further evidence that current audiences continue to love this story, looking back fondly on She’s the Man as a nostalgic high school iteration.
The crux of the film can be summed up in one of my favorite quotes, from a bitter Toby (Brandon Jay McLaren): “How come when I wanted to ask Eunice out, everyone made fun of me, but then Sebastian likes her, and suddenly she’s cool? Screw you guys, I hate high school.” The story defies the norms and made-up hierarchies of high school, as well as society at large. Viola’s mom wants her to be an elegant debutante, but she wants to play soccer. The men’s team won’t let her play, and the guys at her new school, while she’s disguised, find her off-putting because of her earnest, over-the-top way of speaking.
Viola is trying to find her place in a world that tries to put her in a box. Once she shows everyone what she’s been doing to prove herself, it frees them up to violate norms of their own, empowering Toby to ask Eunice (Emily Perkins) out and Andrew (Clifton MaCabe Murray) to seemingly come out of the closet and date Viola’s gay best friend Paul (Jonathan Sadowski).
In the third act of the film, Viola is face-to-face with her condescending ex-boyfriend as he plays goalie on the opposing team in a moment that will decide her and her team’s fate. She has to make this shot, having put everything on the line to prove that women can play just as well, if not better than men. He spews trash talk at her, saying, “I love you. Concentrate. Don’t kick like a girl. Guys are better. Not gonna happen. You’re a loser.” Her eyes are laser-focused, and the antagonization only seems to make her more confident. She, of course, kicks the winning shot. And her ex is left crying.
It seems so unfair that the weight of womankind has to be on the shoulders of one woman in one situation, but it’s so common. Trailblazers have had to persevere in the face of underestimation, barriers, and harassment. Kathrine Switzer made history as the first woman to run the Boston Marathon with an official race number in 1967, despite the race director’s efforts to remove her, among other accostments from fellow racers. Track and field runners Tidye Pickett and Louise Stokes were the first Black women to participate in the U.S. Olympics, still facing hardship like segregation at mealtime and a fellow athlete throwing ice on them in their sleep.
Viola represents the very real barriers female athletes face. Art has a place in politics, even at its most comedic or romantic. A film doesn’t require the Barbie “Impossible to Be a Woman” monologue or Parasite’s (2019) overt socioeconomic commentary for it to be deemed a political work. She’s the Man is a lighthearted film that connects the Shakespearean society of the 1620s, the bubbly humor of the 2000s, and the framework we look at with new eyes in the 2020s.
Plus, there are fabulous lines like, “Girls with asses like mine don’t talk to guys with faces like yours.” So what’s not to love?
Retrospective Courtesy of Risa Bolash
Feature Image Credit to Dreamworks Studios