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Oct 27, 2020 Web Exclusive By Stephen Danay

It would be hard to explain to anyone who didn’t live through it how much teen comedies dominated the multiplex at the end of the 1990s. Beginning with Clueless in 1995 and bolstered by the popularity of teen soap operas on the fledgling WB network, the cycle reached its zenith in 1999, a year which saw the release of American Pie, 10 Things I Hate About You, She’s All That, Varsity Blues, Cruel Intentions, Never Been Kissed and Election, to name a few. All of these films enjoyed either commercial or critical success, so it’s not hard to see why the Warner Brothers marketing machine would take advantage of the zeitgeist when advertising Drop Dead Gorgeous. Unfortunately for them and the film itself, the strategy didn’t work. The film barely made back its modest $10 million budget and critics and audience reactions were tepid to negative.

Two decades later, it’s unsurprising that the teen audiences propelling sex comedies and YA-Shakespeare adaptations to box office gold didn’t have much interest in a dark comedy that shares far more cinematic DNA with the mockumentaries of Christopher Guest than it does with American Pie. Presented as a documentary of the 50th annual Mount Rose American Teen Princess Pageant, Drop Dead Gorgeous is more concerned with skewering the foibles of small-town Midwestern American culture than it is with teen romance or sex jokes. Well, there’s still quite a few sex jokes. The film’s observational absurdity is intertwined with dark humor, focusing on a streak of accidental deaths and injuries that keep picking off pageant contestants during the run-up to the big show. By the standards of a teen comedy, the film has a lot on its mind, and that mind is fairly mean-spirited, so it’s not hard to imagine why audiences stayed away and critics didn’t take it seriously.

Much of the humor in the film is regional, and it’s hard see this movie existing without Fargo having been an Oscar-winning hit four years earlier. Set in fictional Mount Rose, Minnesota - home of America’s oldest living Lutheran - Drop Dead Gorgeous has more than a little disdain for the folksy Protestant charms of the American Midwest. Most of its characters are hapless rubes, outright hypocrites, or some combination of both. Still, the film’s bizarre specificity keeps it from feeling outright cruel. One of the contestants has a talent for imitating dog barks. Another is a white girl adopted and raised by Japanese immigrants who have transformed her into an all-American country girl via their outsiders’ perspective - her answer for who should be president is Emperor Hirohito and her favorite thing about America is its unquestioned atomic power. The only thing that stands out as particularly tasteless is the character played by Will Sasso, a mentally handicapped hardware store employee who’s the brunt of numerous jokes.

The biggest draw of Drop Dead Gorgeous - and likely the main reason it’s become a cult classic in the two decades since its release - is the cast, which features a number of rising stars and familiar favorites, many of them giving the performance of their careers. As the sweet, determined, Diane Sawyer-worshipping protagonist Amber Atkins, Kirsten Dunst makes it easy to see why she was on the cusp of becoming a star. In the year following the release of Drop Dead Gorgeous, Dunst would release The Virgin Suicides, Dick and Bring It On, cementing herself as one of the most versatile and talented actresses of her generation. Amber is a terrific display of her facility for both the girl-next-door charm and sly intelligence that would make her famous. Her rival, the spoiled, glamorous front-runner Becky Ann Leeman, is played by Denise Richards who in 1999 was riding high on the sleazy success of Starship Troopers and Wild Things. Four months after the release of Drop Dead Gorgeous, she would play the improbably named Bond girl Dr. Christmas Jones in The World Is Not Enough. Richards’ bombshell looks and eventual descent into tabloid/reality-TV ignominy make it easy to brush over any acting talent she possessed, but no film made better use of her self-aware sexuality and Chesire cat grin than Drop Dead Gorgeous. Peppered among the other pageant contestants are the always charming and gone-too-soon Brittany Murphy playing a variation on the lovable goof-ball persona she established in Clueless, as well as five-time Academy Award nominee Amy Adams, making her film-debut as an oversexed cheerleader.

The adult cast is arguably as terrific, including Ellen Barkin and Allison Janney as Amber’s coarse but loving mother and friend, respectively. Janney is especially hilarious and her performance here as a foul-mouthed trailer park burnout will come as a fun surprise to anyone familiar with her from The West Wing. Best of all is Kirstie Alley as Gladys Leeman, Becky’s mother and the host of the pageant, as well as a former winner. Predating the reality TV craze for insane dance moms by a decade, Gladys is a poisonous cutthroat dressed up as a lady who’d say please and thank you if you helped her reach a high shelf at Walmart. Alley plays the role with enough self-awareness and spitting viciousness to remind you that she was a talented comedic actress before she became best known as a Scientology-spouting weirdo.

Warner Archives’ new Blu-ray release of Drop Dead Gorgeous is unfortunately barebones, which is a real shame. The cult following the film has developed over the last two decades and the variety of now-famous personalities involved would make it ripe for a retrospective documentary.