It’s Time We Admit The Real Villain In ‘She’s The Man’ Was Olivia Lennox

Utter the words She’s The Man around literally anyone with a shred of taste, and you’ll be instantly met with cries of, “My favourite’s Gouda!” or “C’mon, Paul!” or “Chew like you have a secret!”

That’s because She’s The Man is a universally beloved and outrageously quotable film. It stars criminally underrated slapstick comedian Amanda Bynes as Viola Hastings (and the under-cover version of her twin brother, Sebastian), along with Channing Tatum as beautiful himbo and soccer star Duke Orsino.

But bro – brothers? Brethren? – we didn’t come here today to discuss the myriad ways in which She’s The Man is a perfect film. We’re here because it’s time the film’s real villain was finally exposed.

“But isn’t Viola’s fuckboy ex-boyfriend Justin the villain?” you ask. “What about Monique? Or Malcolm? Or Coach Pistonek?”

All of those characters were shitty in their own right, sure. But none come close to Olivia Lennox. Allow me to explain.

She’s The Man is a modern adaptation of William Shakespeare’s Twelfth Night, in which a shipwrecked Viola – believing her brother Sebastian to be lost at sea – disguises herself as a man to serve the Duke Orsino in Illyria. The Duke is in love with a woman named Olivia, who vows not to court or marry for seven years while she mourns the death of her brother. Until, that is, she meets and falls in love with the undercover Viola.

See what they did there? There are nods to the play’s wry comedic beats throughout the film, but few characters fall further from grace in the adaptation as Olivia.

Sebastian’s icy ex-girlfriend Monique is low-hanging fruit, but her villain status is mostly down to her inability to relate to her boyfriend’s bombastic twin sister. That, and the fact that she can’t (or won’t) accept that their relationship is over.

But you know who else won’t take no for an answer? Olivia. Where Monique’s admittedly ungraceful behaviour draws ire from those intent on embarrassing her for wanting closure from the real boyfriend who ghosted her and took off to London, we’re supposed to believe that Olivia’s unwillingness to accept Fake Sebastian’s rejection is romantic.

If the situation were reversed and it was Fake Sebastian manipulating his way into a relationship with Olivia, would we consider it cute?

Notwithstanding the fact that she’s carrying out a pretty big ruse of her own, Viola, too, cops a number of misdirected reprimands as a result of Olivia’s Teflon-like “good girl” exterior. In the bathroom fight scene, Olivia goads Monique into a fight – in which she enthusiastically participates – and lets Viola take the blame for it when they’re sprung.

Olivia only shows real interest in Viola when she stops being threatened and realises Viola could help her snag the real Sebastian at the end of the film.

There’s not a lot of room for forgiveness when it comes to Malcolm, either: he stalks Olivia and becomes obsessed with exposing what he (correctly) believes to be Viola’s deception. This is likely inspired by the play, in which a character named Malvolio (who you’ll recognise as Malcolm’s escaped pet tarantula) is tricked into believing Olivia is in love with him.  

But in the movie, it is Olivia who hatches her own plan to exploit Duke’s affections for her and make Fake Sebastian jealous. Her hubris is such that she openly admits to Viola at the debutant’s lunch that she’s using Duke to get closer to his roommate (though she does have the sense to pretend she “feels really bad about it”).

Of course, without her deception, we never would have experienced the glory of Duke’s attempted flirtation (“I gotta…ch-change m-my… feet”) or the train wreck double date that follows, but that she could actively hurt beautiful, dumb Duke is perhaps Olivia’s greatest crime.

As movie villains go, Olivia Lennox is nowhere near the worst of them. And she’s certainly not the only person pulling some questionable moves in She’s The Man. But it’s high time we all agreed she got off way lighter than the Justins and the Moniques and the Malcolms, and for that, she’s the film’s real villain.

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You can stream She’s The Man on Stan and Netflix.