When Romance Met Comedy
With When Romance Met Comedy, Caroline Siede examines the history of the rom-com through the years, one happily ever after (or not) at a time.
It’s not hard to give out superlatives to the class of mid- to late-’90s teen rom-coms. The best is Clueless, which reignited the genre after it went into hibernation following John Hughes’ domination in the 1980s. The smartest is 10 Things I Hate About You, with its stellar cast and thoughtful feminism. The weirdest is Never Been Kissed, with its ethically squicky undercover reporter premise. And the raunchiest is obviously American Pie. But the distinction of the most ’90s teen rom-com goes to She’s All That, an urtext for the high school rom-com genre that’s so ridiculous its plot barely even needed to be exaggerated for a big screen parody. 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.
It’s also the film that the Netflix algorithm decided needed a gender-flipped remake starring TikTok’s best and brightest. He’s All That will attempt to capture audiences’ hearts the way the original did when it unexpectedly took the January 1999 box office by storm. Made for a budget of about $10 million, She’s All That went on to earn $103 million worldwide and overcome lackluster reviews to cement itself as a generation-defining teen movie. In fact, the rom-com landscape would probably look a whole lot different without the tropes that She’s All That solidified with its story of school stud Zack Siler (Freddie Prinze Jr.) and his Pygmalion-style bet that he can make any girl prom queen—even artsy loner Laney Boggs (Rachael Leigh Cook).
Like a lot of cheesy rom-coms, She’s All That toes the line between something you enjoy ironically and sincerely. One of the movie’s funniest scenes is entirely unintentional, as Zack melodramatically yells at his dad (Tim Matheson) about the difficulties of picking between multiple Ivy League schools. Yet there are some rom-com moments that are genuinely swoon-worthy too, particularly anytime Cook and Prinze Jr. just stare at each other longingly. It’s that mix that makes She’s All That true camp rather than just campy. While there are moments where it comes close to crossing the Failure To Launch threshold of a rom-com that’s so absurd it becomes a meta parody of itself, there’s just enough heart to keep it in more sincere territory—even as its winking references to everything from The Real World to Pretty Woman let the audience know that it’s (mostly) in on the joke.
It’s why I can’t get too worked up about the sexism inherent in She’s All That’s makeover premise. In fact, I’d argue that, karmically, She’s All That giving us a shared cultural lexicon for dissecting those tropes outweighs whatever problematic elements it put out into the universe to begin with. (“Guys, she’s got glasses and a ponytail… There’s no way she could be prom queen!” Chris Evans laments in the She’s All That send-up, Not Another Teen Movie.) And, anyway, I tend to agree with Mindy Kaling’s assessment that romantic comedies are often best enjoyed as a subgenre of sci-fi, “in which the world operates according to different rules than my regular human world.”
So while there were perhaps some young women who saw She’s All That and decided the only way to win a guy was to put on a slinky red dress and walk down the stairs in slow motion to Sixpence None the Richer’s “Kiss Me,” I suspect that most understood they shouldn’t take meaningful life lessons from a movie that features Usher as a high school DJ who reports on popular kid breakups and directs an inexplicably choreographed group dance number at prom. (Director Robert Iscove—who was coming off the Brandy Cinderella TV movie—was gunning for a job directing the Chicago movie musical adaptation, and was hoping to use the prom scene as an unofficial audition.)
She’s All That is more goofily self-aware than many acknowledge, starting with the funny subversion that Laney is a nerdy outcast who isn’t actually good at school, while Zack is a popular jock with the fourth highest GPA in their class. She’s All That has some genuinely solid comedy throughout, including Zack’s baffled reaction to Laney’s bizzaro performance art and a runner where Laney’s dad (Kevin Pollak) keeps getting Jeopardy questions wrong. When Zack tries to smooth talk Laney with a compliment about her eyes, she retorts with the hilariously convoluted comeback, “Oh, please… You wanna know about art? When the class president starts touching my face on darkened street corners and talking about my eyes, there’s a word for it. There’s an entire movement in the ’20s. It’s called Surreal.” And Iscove also offers a few moments of genuinely creative filmmaking, like a flashback sequence where queen bee Taylor Vaughan (Jodi Lyn O’Keefe) literally brings Zack into her memory of falling in love with fictional Real World star Brock Hudson (Matthew Lillard) during spring break.
Rewatching She’s All That today, what stands out most is how many members of its young cast were destined for stardom—a byproduct, unfortunately, of Harvey Weinstein’s bullish involvement as a producer. Zack and Laney’s high school world is rounded out by characters played by Paul Walker, Dulé Hill, Gabrielle Union, Anna Paquin, Kieran Culkin, Elden Henson, Clea DuVall, Lil’ Kim, and even (via a brief, silent appearance) Milo Ventimiglia. The biggest key to She’s All That’s success is that everyone involved seems to have a keen sense of exactly what kind of movie they’re making. Prinze Jr. put it in John Hughes terms for a 15th anniversary retrospective piece: “Some Kind Of Wonderful was never going to be The Breakfast Club, because that’s this beautiful play that somehow works as a movie, but it was still a movie that reached out to the jocks and the outcasts, and if She’s All That could be like Some Kind Of Wonderful, I thought that would be great.”
The cast all play to the lighter side of the material, and the leads come across as the two most non-threatening human beings in the world. Cook’s Laney is like a training wheels version of an angry alt-girl—especially compared to the much more authentically “scary and inaccessible” performance Julia Stiles gave in 10 Things I Hate About You just a few months later. Laney’s prickly posture feels like such an act that it barely even registers when Zack helps her strip it away. In fact, it’s Cook’s inherent sweetness that makes it so memorable when Laney unexpectedly gets to deliver the PG-13 movie’s one f-bomb: “Am I a fucking bet?!?” The iconic line was written by none other than M. Night Shyamalan, who did an uncredited polish on R. Lee Fleming, Jr.’s original screenplay.
Prinze Jr., meanwhile, is pitch-perfect casting for a teenage soccer bro—an archetype that offers a different energy than the aggression of a football bro or the entitlement of a lacrosse bro. As a soccer bro, Zack has the confidence of a jock but also the sensitivity to look out for Laney’s little brother with a casual “Everything copacetic?” He’s gotten into impressive schools like Yale, Harvard, and Dartmouth, only to let half the admissions acceptance deadlines lapse because he’s so racked with indecision. He’s obsessed with his social standing at school, but also so lacking in self-consciousness that he casually improvises a hacky sack spoken word poem at an avant-garde performance space. For all his academic prowess, Zack is mostly just a sweet, dumb himbo, which makes it easier to give him the benefit of the doubt when he says things like, “I made that bet before l knew you, Laney. Before l really knew me.”
In fact, it probably makes more sense that Laney falls for the misguided but clearly kindhearted Zack than it does that Eliza Doolittle falls for the haughtily cruel Henry Higgins in the other famous Pygmalion riff, My Fair Lady. If there’s a thesis to She’s All That, it’s that high school is a strange ecosystem where social hierarchies and boundaries are less rigid than they seem to be—and where pretty much everyone needs to be reminded that the identity they’ve carved out as a teen doesn’t have to be the one that follows them for their whole lives. Zack brings Laney out of her shell and shows her she can fit in wherever she chooses, which will presumably give her a greater sense of confidence as she heads off to art school. Laney, in return, gives Zack a much-needed dose of humility and perspective that will serve him well outside of his high-school bubble. As in Pretty In Pink, they’re a star-crossed couple who absolutely won’t last past a summer-before-college fling. But not all rom-com romances need to last forever to be sweet in the moment.
In the end, She’s All That explores the ’90s teen experience in much the same way the Frankie Avalon/Annette Funicello Beach Party movies riffed on the 1960s one—not with actual verisimilitude, but with an exaggerated aesthetic that feels true to the time in a different kind of way. She’s All That is a glitter and butterfly clip time capsule of a moment that never really existed outside of the pop culture that made it feel like it did. And though the film has all the sustenance of a piece of bubblegum, it takes a rare blend of savvy intelligence and complete guilelessness to pull off that particular kind of sugar rush. He’s All That has some big ankle-strap heels to fill.
Next time: Ever After did the Cinderella story right.