With a little bit of squinting, this premise is recognizable as a take on Pygmalion (both the Greek myth and George Bernard Shaw’s 1912 play, which itself formed the basis for My Fair Lady). But it’s quite remarkable that, despite the supposed march of progress since then, Shaw’s circa-turn-of-the-century Eliza Doolittle remains the most feminist of the popular Galateas (the figurative statue turned into a real woman by Pygmalion).
—I bet there are vague spoilers below (but only if you’re surprised by basic rom-com conventions)—
Much as in other modern adaptations of the myth (Pretty Woman, S1m0ne; as well as, admittedly, the original), the female lead in She’s All That is robbed of most agency. Unlike Eliza, she doesn’t know about the bet, and doesn’t willingly agree to becoming a project; also unlike at least Shaw’s original Eliza, she’s rather easily wooed by simple romantic gestures at the end of the film. One moment of demonstrating her ability to stand up for herself against male aggression is even relegated to off-screen and played for laughs.
The stakes aren’t as high, either, pared down to the concerns of a teenage audience. Eliza Doolittle wants a way to transcend class she is born into; the big development for Laney is opening up a little emotionally and socially (though why she should do the latter given the shallow denizens of Zack’s social circle, of which a would-be date rapist played by, of all people, a young Paul Walker, is only the second-most disgusting, is never satisfactorily explained). She also has to acquiesce to a physical makeover with the typical Hollywood message that glasses, individualised hair and dress choices, and a lack of make-up and eyebrow grooming are all very, very bad, and only by conforming to other people’s beauty standards can you become a complete and well-liked person.
No, it’s the male lead who learns the more valuable lesson: despite being super-smart, physically attractive, athletic and wealthy, he’s vaguely uncertain of his future and resents his successful father’s expectations. His adventure with Laney doesn’t teach him not to lie to girls (in fact, he never apologizes for making her the unwitting object of a bet, at least not to her; apparently he says sorry to her father and brother, if their reactions to his reconcilement with Laney are an indication); it teaches him to deal with his daddy issues. The plot is in service of Zack’s “growth”, not Laney’s, despite lip-service from Laney’s art teacher to the contrary.
This unfortunate, but rather typical-for-the-genre regression aside, She’s All That is mildly entertaining, though wildly dated in its use of teenage slang and music (the number of imitation-ready dance/song sequences is, unfortunately, higher then one); also, weirdly, the film seems to want association football to be a thing in U.S. high schools in 1999 (a concession to international viewers?). But the film never rises above (mostly) predictable teen rom-com mediocrity, despite the potential of the source material (for example, a dream sequence showing Zack’s fear of being played by Laney instead of the other way around suggests an interesting reversal, but doesn’t go anywhere). Its biggest failing is that it doesn’t really commit, but tries to be as bland as possible to appeal to the widest possible audience. Progression doesn’t come from the characters, but because the plot needs to be kept moving, leading to lots of silly contrivances; so both the central prom plot as well as the character development of the protagonists can’t help but fall flat.