“To everyone here who matters, you’re spam. You’re vapor. A waste of perfectly good yearbook space. Nothing’s ever going to change that.”
We bet you can’t make that girl with glasses listen to this podcast. In our latest episode, we look back to the teen movie explosion of the late 90s via She’s All That, Never Been Kissed, and 10 Things I Hate About You, all released in the first few months of 1999, and all culminating at — where else? — the prom! (Gasp!)
If you don’t think Drew Barrymore, Rachael Leigh Cook, and Julia Stiles are three of the world’s least desirable women, you may have trouble buying the mischief and shenanigans teen boys resort to in search of true love. This was the moment in pop culture when teen entertainment took a cue from Shakespeare and other classic literature — without doing much to update centuries-old sexual politics. If you thought 80s teen comedies were problematic, wait ’til you get a load of the sexist, stalkerish antics of 90s dreamboats like Freddie Prinze Jr., Heath Ledger, Andrew Keegan, Paul Walker, and Joseph Gordon Levitt!
Are any of these 1999 prom-coms “all that,” or are there 10 things to hate about each? We hope you rented a limo to fit all the snark, angst, and inappropriate romance of these teen comedies!
It seemed perfectly normal at the time. A bunch of adults in designer outfits, strutting around sleek high school hallways, impersonating minors. (In the case of Never Been Kissed, impersonating minors who are impersonating minors.) The jocks and prom queens rarely attended class, never did homework, and spent most of their free time playing pimp or placing high-stakes bets on who can destroy a girl who’s already the most humiliated girl in school.
They were never realistic. Growing up in the 90s, we never believed that this is what other teenagers looked or sounded like, except maybe in Beverly Hills. But this was what “cool” was, according to Freddie Prinze Jr. and Julia Stiles and the WB and MTV. Teen-oriented romantic comedies were never exactly the coolest thing pop culture had to offer, but still, they depicted a lifestyle that was meant to be desirable to us — a high school experience that excelled in every way beyond our own.
So-called “teen movies” have always been fluff, from Beach Blanket Bingo to The Breakfast Club. The romances in John Hughes’ Molly Ringwald trilogy were much too starry-eyed to ever be real, but Ringwald’s characters were always relatable, even if everyone around her was a vile creep (as in Sixteen Candles). By the late 90s, real teen emotions were gestured to, but mainly used as a plot device. It’s hard to feel too bad for these girls — they’re all so pretty!
Clearly, 1999 was a peak year in teen-oriented cinema, some of it good, a lot of it not so good. We could — and perhaps will — do another podcast on the movies we had to leave out. What become clear looking at the three frothiest titles from this year is how much they had “borrowed” from Clueless, and how little they understood about what made that movie work. Clueless isn’t just a teen a movie — it’s a satire of wealthy Los Angelinos, stemming from Jane Austen’s Emma. Teen movies of the late 90s aped Clueless‘ aesthetic minus the satire — by this point, we were just meant to accept that high schoolers all across America were this articulate and chic. These movies were also based on literary classics, for the most part… but a lot of them forgot to update the blatant sexism that was par hundreds of years ago for the 90s.
SHE’S ALL THAT
January 29, 1999
Budget: $10 million
Opening Weekend: $16.1 million
Domestic Gross: $63.4 million
Worldwide Gross: $103.2 million
Metacritic: 51
I remembered She’s All That primarily by Sixpence None the Richer’s overplayed “Kiss Me” and the image of Freddie Prinze Jr. and Rachael Leigh Cook slow-dancing in formal wear. (Okay, and Sarah Michelle Gellar’s “declining fresh pepper” cameo, the true highlight of the movie.) The PG-13 teen movie was no exactly my jam. By those standards, She’s All That was adequate, and I never felt a strong urge to watch it again.
So I had more fun revisiting this one than I expected, mostly because there’s so much going on. Freddie Prinze Jr.’s “big man on campus” Zack is cardboard — his main problem in life is that he got into too many colleges. Rachael Leigh Cook also makes for a pretty weak geek — after the big makeover, the vibe we get from her isn’t, “Wow! Look how much prettier I am!” but “At last, I have returned to my natural state.” Aside from a nice moment or two, this romance is a dud.
But there’s also Anna Paquin as Zack’s precocious little sister, Laney’s likable buddy Jesse Jackson, Matthew Lillard as an outrageous MTV Real World star, and Jodi Lyn-O’Keefe as a fairly formidable queen bee bitch. Usher DJs over the school intercom — is he supposed to be a student here? Lil Kim is hanging around, for some reason. A bully tries to make Kieran Culkin eat pubes, and some random guys compose an on-the-fly rap containing the film’s title. Zack has to do hackey sack slam poetry in his most charming scene, and ends the film shamelessly showing all his peers and their immediate family what he looks like naked. Best of all, everyone does a choreographed dance to Fatboy Slim’s “The Rockafeller Skank” at the pro, which I would have been so down with in 1999.
None of this quite gels together, despite the efforts of M. Night Shyamalan, who did some significant rewrites. But it was a lot more fun than the gooey teen romance I was expecting. I was never bored for a moment. Even the occasional cringes were entertaining. She’s All That is not the finest specimen 90s teen culture has to offer, but it was an amusingly bizarre reminder of just how high school was packaged in pop culture back then. Seriously, these movies set terrible examples for teenagers on every level.
10 THINGS I HATE ABOUT YOU
March 31, 1999
Budget: $30 million
Opening Weekend: $8.3 million
Domestic Gross: $38.2 million
Worldwide Gross: $53.5 million
Metacritic: 70
I thought I’d like this one. I really did. I remember having a good time when I saw it originally — it’s probably the only one of the three I saw in theaters. But I never watched it again, and thus, was in for a rude awakening in this reexamination.
I didn’t talk much about the problematic sexual dynamics of She’s All That, and that’s because, as terrible as they are, I found 10 Things I Hate About You so much worse. The bet made in She’s All That is cruel, but in 10 Things I Hate About You there are multiple people offering and accepting money in exchange for dating “services,” and most of that is just meant to manipulate people. Joseph Gordon-Levitt pops out of nowhere as a new student and falls madly in love with Larisa Oleynik before she’s said a single word. He convinces his dorky, Shakespeare-loving friend to manipulate Andrew Keegan and Heath Ledger into dating the Stratford sisters, because their overbearing dad is fond of arbitrary parenting rules that feel like they were thought up in the 1500s. (They were.) None of this is grounded in any logical motive, and Julia Stiles’ supposedly “rebellious” Kat and Ledger’s “dangerous” Patrick would be warmly welcomed on Sesame Street. He stalks her through town and mocks her for being a feminist — which is slightly understandable, because she’s pretty obnoxious about it — but it isn’t long before she’s all dewy-eyed for this jerk. Yes, this is essentially the Pygmalion-inspired plot from She’s All That, except this is Shakespeare, and a lot less has been done to make this plausible in the 20th century. Kat is supposed to be a “shrew,” and 10 Things I Hate About You can’t even be bothered to put glasses on her.
I like all of these actors elsewhere, so I was surprised to find myself wholly uncharmed by them here. Maybe I could have gotten over this if even the movie’s title wasn’t a sham. (Putting “and” between two things doesn’t make them one thing, Kat! There are 14 things you hate about him!) With its father-daughter focus, 10 Things I Hate About You feels most beholden to Clueless, but it’s sorely missing that film’s confidence and craft. It’s also the most ignorant of moral consequence for its characters’ gross behavior of any of these three films, which is surprising coming from a female screenwriter. 10 Things I Hate About You is the most fondly remembered of this 1999 prom-com trilogy, but for me, it was also the falsest and most off-putting.
How many things did I just say I hated about this movie? Ehh, let’s just call it ten.
NEVER BEEN KISSED
April 9, 1999
Budget: $25 million
Opening Weekend: $11.8 million
Domestic Gross: $55.5 million
Worldwide Gross: $84.6 million
Metacritic: 60
I had very little memory of Never Been Kissed beyond what was in the trailer, and had no idea what I was in for. Pleasantly, I discovered that this movie is bonkers.
How bonkers? Well, the editor-in-chief of the Chicago Sun-Times tells a lowly, mousy copy editor that she’s going to sneak back into high school to get the scoop on… something! They’ll figure that out later. First, 25-year-old Josie has to wind the clock back seven years and become Josie Grossie again. She attempts to be a cool kid this time around, of course, but that backfires until she meets a cute guy (in high school, who may be a minor) who likes her. Around this time, Josie’s brother also decides to pose as a teenager and return to high school, in order to relive his glory days. (He peaked.) This involves the siblings tell everyone at school they used to date. He also proceeds to date minors.
Never Been Kissed doesn’t find any of this problematic, as if it’s okay to date underage if you tell them you’re underage, too. But that’s not even the worst of it, because then Josie’s teacher develops the hots for her, and he believes that she is also a minor. It’s a wacky Shakespearean love triangle, but this statutory rape!
This is only a simmering problem in the film, since nothing else is that plausible, either. Why is Josie being paid for weeks to do nothing but attend high school, when there’s nothing notable to find out? Why must the poor readers of Chicago be subjected to this lame story? The only actual “news” that emerges from Josie’s investigation is the inappropriate flirtation of Mr. Coulson with a student — which, again, doesn’t inspire nearly as much outrage as you’d think. The rom-com ending ignores all the problematic details of this unconventional courtship. They don’t even mention it, and probably never will. This movie’s title is a blatant lie, too, by the way.
Despite all this, Never Been Kissed is breezy and engaging. It’s really not taking itself seriously, even by teen prom-com standards. It has a pretty strong cast, from Drew Barrymore to David Arquette to Leelee Sobieski to Michael Vartan to James Franco. It’s not a must-see by any means, but it amused me.
REAL NOBODY 