That Moment in ‘She’s All That’ (1999): Never Let Them See Me Cry

The ugly duckling transformation as a movie trope is one of the oldest and most successful in movies. From long ago classics to modern times, the Cinderella story remains one of the more tried and true formulas in Hollywood, with countless iterations and interpretations. In teen movies especially, the would-be beauty blossoming on screen has lured many into the theater. And so it was for 1999’s romantic comedy, She’s All That.

It starts when high school heartthrob Zack Siler (Freddie Prinze Jr.) gets dumped by the hottest girl in school (Jodi Lyn O’Keefe) after she runs off with a perfunctorily conceited reality TV star (Matthew Lillard). Zack goes on the defensive and claims that any girl can be hot, which inspires his best friend Dean (Paul Walker) to proffer a challenge: turn any random girl into the Prom Queen in six weeks. Zach accepts, and they settle on nerdy art student Laney Boggs (Rachael Leigh Cook), much to Zack’s dismay. Little does he know what awaits.

Very well directed by Robert Iscove, She’s All That is another film adaptation of Pygmalion by way of My Fair Lady. While it doesn’t break any new ground, it does have some freshness nonetheless, with an observational charm to it that seems to understand that its own plot is a hackneyed one. The filmmakers proceed with the formula with standard fare but populate the peripheral with a lot of great moments and humor that betray a wink and a nod to those carefully watching. While pleasant and innocuous as a teen romantic comedy that projects all its surprises long before they happen, it’s these carefully constructed moments that give the film its heart. The leads are well-cast, and while the story is forced by the very rigid structure to come to its inevitable conclusion, it’s better than most in its pool of look-a-likes.

Never Let Them See Me Cry

It’s no surprise that yes, the dorky, awkward, clumsy Laney Boggs is in fact, a beautiful, radiant, shapely young woman once she sheds the (*sigh*) glasses and exchanges her frumpy loose tops and pants for a skin tight, low-cut fire-red dress. There’s no changing that conventional reveal and indeed, it ranks as one of the greats in the tropey beautiful-girl-we-didn’t-think-was-descends-the-stairs-in-slow-motion moments.

Furthermore, the fact that Zack has fallen in love with the once shunned girl is also nothing we didn’t expect. But She’s All That doesn’t quit there–as many films of this genre do. Dressed for a party, Laney must face the big hurdle, the cruel and yet somehow incredibly popular Taylor Vaughn, Zack’s ex-girlfriend. She’s wearing nearly the same dress and has thought of Laney as a worthless girl her whole life, appalled that her poolman’s daughter could be attending this get-together. She’s a real piece of nasty work. She confronts Laney and in front of everyone, publicly humiliates her by pouring a drink down her front and calling her a waste of Yearbook space (a decidedly catchy insult). Laney does pretty well with it all up that point and finally breaks down, running off in tears, much to Taylor’s delight.

Zach of course, like all kids in attendance, is watching. He takes after his date, running right past his former flame, clearly upset with what he just witnessed. And here’s where things take a turn from what we expect. We expect he will save her, that he will rush in and sweep her off her feet, to put Taylor in her place and be the hero. But instead, this moment is not about that but rather Laney herself. This is really critical and further reveals how the makers are trying to go in a different direction. Let’s take a closer look.

There’s a lot about the confrontation with Taylor that establishes much about the relationship between them and Laney’s perceived status in the fixed group. Taylor is the dominate figure, taller and more aggressive, she looks down upon the fragile-looking Laney as if she truly believes she is lesser. What’s more, she deliberately pours her drink into Laney’s dress, making no effort to make it even appear like an accident. This is a strikingly puerile gesture and yet demonstrates a blatant disregard for what Laney thinks of her, but a move so bold as to think that all around would condone the act, which everyone seems to do. Little does she know though, that the silence of those in the room is not one of acceptance. But that comes later.

When Laney rushes outside, she trips and falls in the driveway, surrounded by the expensive cars the party-goers arrived in, crumbling in defeat at the lifestyle that she now feels even more separated from. Zach comes to her side and knees beside her, gently putting a hand on her shoulder, but she demands he not touch her, which is crucial. Laney is not to be taken care of, but more so, wants no pity. What she is feeling is hers alone and Zach, no matter his intentions, is not invited to her pain.

His comfort is not so much unwelcome as ineffectual. She is hurt by Taylor, but it’s much more than that. She let them see it. Through her tears she says she had promised herself that she would never let them see her cry, and this confession has great impact on Zack, who watches her with not only sorrow for what happened, but a much more meaningful reason. Laney Boggs was a nothing to him just weeks before, a girl in the corners of his life, one to be mocked and ignored, and in truth as lowly to him as she is to Taylor. So two things are happening here. First, Laney is literally and emotional tumbled. She had been able to fend off the disparagement from Taylor and her like because she was always on the outside of it, but now, she was on the inside, in the coveted room, as it were, but she found, just as she suspected, it takes more that a pretty dress to get into that circle. You must be born into. Her father’s low income job and Laney’s nebbish clothes make her an easy target. Second, Zack is having a transformative moment, an emotional punch to the gut that has awoken the truth about who he really is (or was).

Both Cook and Prinze Jr. are at their best here, in a gripping and surprisingly raw moment that feels almost unscripted. The film maintains a practiced distance from reality for the entirety of the story, purposefully keeping the setting and themes a bit like a twisted fairy tale, except here. Suddenly it gets real. We expected after she stormed away that she’d be walking away with Zack following behind. Then we’d see the big argument scene, where she would hate him for making her change. That’s what we expect. That’s what happens in all of these movies. What we get instead is this highly personal and vulnerable moment that reveals how deeply this pain she feels is set. And it makes a big difference. We already sympathize with Laney; now we empathize as well.

When she tells him she wants to go home, there is a heartbreaking moment of silence as Zack understands it all and simply says, okay. He then offers his coat, waiting ever-so-slightly for her acceptance, and then drapes it over her shoulders, walking her away. Much has been learned and much will change.