Craig D. Lindsey
It always surprises me whenever someone admits that they have a special place in their heart for She’s All That. In 2021, the AV Club’s Caroline Siede proudly proclaimed her adoration: “She’s All That is self-aware without being satirical, knowingly preposterous but also utterly earnest. ‘The essence of Camp is its love of the unnatural: of artifice and exaggeration,’ Susan Sontag once wrote. By that definition, She’s All That is a high-camp masterpiece.”
Yes, the ‘90s rom-com was a major hit (costing around $7-$10 million and grossing over $100 million), launched the careers of a lot of young stars, and kicked off a teen-movie resurgence that went on all through 1999 (aka the Greatest Movie Year Ever Fight Me On My Momma and Everything I Love™). But we shouldn’t forget that it’s also one ugly, morally reprehensible film. So of course, it came from Harvey Weinstein.
The story goes that Weinstein wanted to make a “piece of shit” film, just to prove he could roll with the major studios and also churn out mediocre, moneymaking product. Instead of releasing it through little brother Bob’s genre-friendly, Dimension Films wing, Weinstein gave it a full-on Miramax rollout. Despite Disney CEO Michael Eisner warning Weinstein that he’s “fucking with the brand name” by going mainstream, by the time That hit number one in its opening weekend, Weinstein was officially in the teensploitation business.
Directed by Canadian choreographer/TV director Robert Iscove (he did that racially diverse Cinderella movie with Whitney Houston and Brandy) and scripted by R. Lee Fleming Jr. (a beholden-to-Harvey M. Night Shyamalan did a script polish), That is one of many ‘90s teen films that reimagines a classic work. In this case, it’s the George Bernard Shaw play Pygmalion, later famously revamped as the musical My Fair Lady. Set in one of those tony, California-based high schools that look more like a resort, the Henry Higgins of this story is Zach Siler (Freddie Prinze, Jr.), a BMOC whose girlfriend (Nash Bridges eye candy Jodi Lyn O’Keefe) breaks up with him, as she’s allegedly found true love with a reality-show himbo (Matthew Lillard, goofy as hell).
With the prom just weeks away, Siler is desperate for a date. He agrees to a bet with his buddy (Paul Walker, not yet living fast and furious) where his bestie must pick an undateable girl Siler has to turn into prom-queen material. And that’s where Laney Boggs (Rachael Leigh Cook, who played a young Parker Posey in the MIramax-released The House of Yes, which also starred Prinze), aka our Eliza Doolittle, literally stumbles in. Boggs is the school’s resident outcast, a four-eyed klutz who is loathed by most of the student body for basically being working-class and into art. Even a goth girl (future Veep alumna Clea DuVall) tells her she should take a cue from other late, great artists and commit suicide.
Out of all the problematic high-school flicks of that year (do I have to bring up all the obvious sex crimes that happened in American Pie?), I always found That to be the most mean-spirited. When I reviewed the movie before its release (yes, I’m that old), I said the films had more in common with the black-hearted “comedies” of misanthropic indie auteurs Neil LaBute and Todd Solondz than anything John Hughes gave ‘80s audiences. It’s like a mashup of In the Company of Men and Welcome to the Dollhouse, with wardrobe provided by Urban Outfitters.
Like most teensploitation films of that era, That gives us an exaggerated, damn-near-fantastical view of adolescence. After all, it would have you believe that a conventionally attractive girl like Boggs, who’s too preoccupied with working and taking care of her widowed dad (Kevin Pollak) and eccentric brother (baby-faced, future Emmy/Oscar winner Kieran Culkin) to deal with Siler and his sudden interest in her, is seen as, according to Siler, “scary and inaccessible.” We eventually get to that tired trope of turning the geeky-but-cute gal into an all-out smokeshow. Before Siler takes her to a party, Boggs gets a pointless makeover by Siler’s sister (Anna Paquin) that’s really just a haircut, a nice dress and, as always, no glasses. As Jesse Hassenger said in a 2019 anniversary piece, this movie “inhabits a world that can hardly conceive of unattractiveness, or any genuine strife.”
That does go about subverting the teen-movie genre in other ways. Siler’s really the nerd — a jock with the fourth highest GPA in class and a stack full of acceptance letters from Ivy League colleges — while Boggs is an arty but average student. It also features Black and Brown actors (including Gabrielle Union, a pre-West Wing/Psych Dule Hill, and X-rated rap princess Lil’ Kim) playing popular kids. Perhaps the oddest appearance from a performer of color is the school’s resident DJ(?), played by R&B star Usher. Fresh from doing a bit role in Robert Rodriguez’s sci-fi thriller The Faculty, another Weinstein-backed teen flick, the singer appeared in reshoots that tied in to the Fatboy Slim-scored dance number (originally written as a random-ass thing that happens) in the climactic prom sequence. In a 2019 oral history, Iscove admitted the number was a demo reel for the Weinsteins, who were considering him to helm their upcoming musical Chicago.
The dance number is indicative of how all-over-the-place That is. There are earnest moments between Prinze and Cook placed alongside scenes that go from slapsticky (mostly done by Lillard) to gross (it makes high-school pizza even more disgusting) to downright cruel. And there’s also the rampant misogyny, not to mention the cringey datedness of it all. Just the title alone sounds like a decision made by old white guys who think they know the latest street lingo.
While I would get my more authentic teen-entertainment fix later that year with the short-lived, star-launching TV dramedy Freaks and Geeks, all the teen girls spent 1999 going to see movies like She’s All That, and swooning over guys who put girls through manipulative, gaslighting shit — and ending up together anyway.
“She’s All That” is streaming on Paramount+ and MGM+, and is available for digital rental or purchase.
“Crooked Marquee’s Bad Romances” is an annual spotlight on anti-Valentine’s Day favorites. Follow this year’s recommendations here; you can also read our entries for 2025, 2024, and 2023.
