When Drop Dead Gorgeous was released in 1999, it didn't quite fit in with the other teen movies that were major hits that year. It didn't have the Sixpence None The Richer-soundtracked revenge glow-up or transcendent hacky sack scene of She's All That; the post-riot grrl feminism of 10 Things I Hate About You; or the raunchy sexual exploration (and I don't just mean the infamous pie scene) of American Pie.
Drop Dead Gorgeous was a whole other beast, using mockumentary-style filming to tell a bizarro tale of small-town pageant girls trying their best to not get killed by a crazed pageant mom. And just as She's All That and its film brethren have become cultural touchstones of the Y2K era, so has Drop Dead Gorgeous, though it took an approach that didn't fit the mold of the teen movie, tackling teen girlhood with an unhinged level of absurdity that still resonated with our experiences.
The camera pans through the flat suburbs of the fictional town of Mount Rose, Minnesota, as "Lost Picasso" by Hot Sauce Johnson (a song and band that couldn't be any more 1999 if it tried) plays. The year is 1995, and a (fictional) documentary team is there among the 5,076 residents in the staunchly Lutheran town to film the 50th anniversary of the Sarah Rose Cosmetics American Teen Princess Pageant, let by local chairwoman Gladys Leeman (Kirstie Alley). Among those vying for Mount Rose's next American Teen Princess are ditzy cheerleader Leslie Miller (Amy Adams); dreamer Amber Atkins (Kirsten Dunst), who wants to emulate her two former-pageant-girl heroes, Diane Sawyer and her mom; and Gladys' daughter, mean girl Becky Ann Leeman (Denise Richards), whose competitive psychosis has her firing bullseye shots into a paper target at a shooting range.
But Lisa Swenson (played with endearingly manic, off-the-wall energy by the late Brittany Murphy) has the most compelling reasoning for entering the pageant: "If you're 17, and you're not a total fry, it's just whatcha do." What follows is a completely bonkers and hilarious story of these small-town Minnesotans' quest for the crown, and one rich, powerful, and murderous pageant mom's no-holds-barred attempts to get her daughter the win she wants. It all culminates with one of the most epic barf scenes in film history, the downfall of the evil Leemans, the crashing down of the Sarah Rose Cosmetics corporation, and Amber finding her way to her dream career despite a million setbacks.
The storytelling upends the teen films of the time, and of any time before.
The girls don't yearn to land their respective dream boy; they don't get cool mid-90s dELiA*s-inspired makeovers that leave their popular girl arch-nemesis seething, and they certainly aren't sexually awakened by getting to any base with a hot apple pie. They're too busy trying not to get clapped by a crazed mother-daughter duo — Gladys and Becky Ann — and striving to break out of the confines of their small town, where the American Teen Princess title may get them little more than a job at the local hot dog factory and a starring role in a commercial selling pork products. For Amber, a happy ending means more than winning the popular boy's affections or even getting the crown. Winning the crown is a shot at escaping her trailer park upbringing and showing that even though she's poor — and has a kind of skanky (but loving!) mom and has to work as the hair and makeup artist in the town's funeral home to help out at home and be able to practice her tap dancing — that she can be something, because she works harder than anyone else and has real talent. So long as the Leemans don't get their hands on her, Amber has a chance, and her perseverance in the most intense of situations is the greatest weapon in her arsenal.
Getting the attention of the dreamy football player isn't Amber's priority, though it's nice while it lasts (shortly after, he meets his untimely end — the victim of a very suspicious hunting accident). In fact, the film easily passes the Bechdel test, with discussions between its female characters mostly revolving around the pageant, evading murder, and whether or not they're actually being filmed for an episode of Cops. (Eventually, it turns out, they are, and it's truly a chef's kiss moment.)
Unlike She's All That or 10 Things, the film's resolution isn't a satisfying rom-com trope about the misfit landing the cutest boy in school, but rather a show of triumph about a young girl overcoming the odds of her class and the unfairness that comes with living in a town where, as Loretta puts it, "it's front-page news" if one of the rich, ruthless Leemans "takes a shit."
At its core, Drop Dead Gorgeous gave us a wild, absurdly portrayed story that's fundamentally about small-town struggles and overcoming the adversity of being born into a class that lacks opportunities to ultimately earn the life you've dreamed of for yourself. It's unabashed weirdness and mockumentary-style filmmaking made it an immediate cult classic that perhaps didn't resonate as easily as She's All That or 10 Things I Hate About You on a large-scale, but did with the kids who saw themselves mirrored in the misfit characters.
In 1999, this was the story for teen girls who had to work after-school jobs to help save for college; the teen girls that didn't fit in because they were considered weirdos; the teen girls who laugh their asses off watching a room full of pageant girls cover a pageant stage in vomit. And it's for girls dealing with the same stuff now. It's a reminder to be the Amber persevering in the face of adversity and to avoid the shellfish if it looks a bit sketchy.
She's All That and 10 Things I Hate About You explored the lives of high school misfit girls: Laney Boggs (Rachel Leigh Cook) was the artsy, working-class "freak" and Katarina Stratford, the bitchy riot grrl unafraid to speak her politics. Both Laney and Katarina undergo a sort-of inner (and in Laney's case outer) transformation to find a softened version of themselves, found through the power of love and foam Rocket Dog flip flops. The girls of Drop Dead Gorgeous don't get that little pink ribbon tied at the end of their story, and the film is a million times better for it.
The casting in Drop Dead Gorgeous is perfect, stacked with women who were or would go on to be some of the strongest character actors and leads in Hollywood. Alison Janney steals every scene as Loretta, the horny best friend to Amber's mom (played by an equally mesmerizing Ellen Barkin as the post-prime MILF). Amy Adams' bit part as the spacey, sex-fueled teen Leslie evokes a woozy Marilyn Monroe, and Brittany Murphy is so unabashedly frenetic and spunky that it makes our loss of the young star feel even greater. The pageant's contestants embody the broad range of weirdo archetypes that we remember from our own high school days, and within one or a few of them, you might even see a version of yourself (if you, too, were a teenage misfit).
Originally Appeared on Teen Vogue