She's All That (1999)

I'm surprised that Harvey Weinstein thought this movie was a "piece of shit" (actual quote) given that it celebrates a guy exploiting a power imbalance and harassing a woman into having sex.

Anyway, this was one of the last examples of 'prepsploitation' in the mould first set by Amy Heckerling and John Hughes in the 1980s, and you can somehow feel that this earnest coming-of-age story could no longer be made in such an increasingly irony-pilled culture. Indeed, the next phase of school-bound movies would fragment out into the sarcastic and sassy (eg. Mean Girls), deliberately 'bad' (Napoleon Dynamite), hyper self-aware (Brick) or 'deep' (Donnie Darko). It's not that the underlying idea doesn't have an audience — I mean, this lukewarm Pygmalion was itself reheated into Ugly Betty (2006—2010). But it's more that it could no longer be inserted into the seemingly sincere framework of the 'high-school movie'.

It's somehow indicative of this malaise that nobody's hearts seem to be in it throughout She's All That and that there's something oddly flat and tired about every aspect of this film. Even the funniest line ("His Dad is the manager of Harrison Ford." / "The actor?" / "No, the car dealership.") is just passed over without even the movie appearing to enjoy it. And the camera's relentless oogling of the the bodies of these school-aged kids feels weirdly uninterested in their bodies by the standards of 1999. Moreover, the school's DJ doesn't seem to care about the plot he is explaining back to us, either — not to mention the metatextual laziness inherent in Usher's character given that it was itself sloppily transplanted straight from Spike Lee's Do The Right Thing (1989), without understanding its cinematic origins in The Warriors (1979), and, long before that, in the χορός; the Greek chorus. Hell, the film doesn't even bother to commit to the conceit that she is unattractive at the start of the movie! Why not simply make her a goth who is angry about her mother being dead? It wouldn't have made the ugly sexual politics any better, but at least the movie would have stakes!

Anyway, the 'hackey sack' sequence was weirdly good. I mean, I'd genuinely go to bat for this kind of performance art, and Prinze inadvertently captures the fragile nature of Zach's high status in the school in his multimedia poetry reading. He should do art at Dartmouth for sure.

You can tell director Robert Iscove would have made it a musical if that had been remotely in fashion at the time [—] the school in the movie looks like some kind of feeder institution for MTV, underlined when prep hero Zack Siler (Freddie Prinze Jr.) loses his queen-bee girlfriend [to] a fictional Real World cast member [as] none other than Usher serves as the all-seeing […] school DJ. […] The best way for these fake-ass high school movies from 1999 to take on some genuine feeling is to wait 25 years, at which point a rewatch feels like a reunion [of famous stars].

— Jesse Hassenger (Paste Magazine)

Although it's questionable whether this story has ever been done well, that hasn't stopped filmmakers from repeatedly trying. She's All That is the latest failure.

— James Berardinelli (ReelViews)