The late ’90s and early ’00s gave us some of the best teen comedies since the days of John Hughes: Can't Hardly Wait, 10 Things I Hate About You, Never Been Kissed, She's All That, and then some. While these have become bona fide classics among millennials of a certain age, one film has achieved cult status – due in large part to its inaccessibility on streaming platforms and its sporadic, unpredictable airings on cable: Drop Dead Gorgeous. Featuring an all-star cast – arguably even by today's standards – led by Kirsten Dunst, director (and former The State member) Michael Patrick Jann's mock-doc combined our obsession with true crime and similarly morbid fascination with beauty pageants into a single, hilarious story of small-town dreams and deadly ambition, evocative in some ways of Gus Van Sant's To Die For. Finally available to stream (on Hulu) for the first time in recent memory (and perhaps ever), Drop Dead Gorgeous remains every bit as darkly comedic and irreverent in 2019 as it was in 1999 – a year synonymous with JNCOs and Delia*s catalogs; a time when Gwen Stefani's cultural appropriation was naively perceived as endearing and weirdly aspirational; an era filled with Limp Bizkits and Korns and Nu Metal groups with aggressively misspelled names one Doc Marten-clad step removed from the prolific "S" symbol scrawled on every available surface. It was a time.
It was also a time when movies like Drop Dead Gorgeous flowed as freely as Fruitopia, the availability of which we took for granted in hindsight (the films, not the Fruitopia – which can and should remain buried in the bowels of consumer hell). Revisiting Jann's film 20 years later comes with the expectant hesitance – has it aged well? Are the jokes offensive in our newly-woke socio-political landscape? Did we ever really get Denise Richards? The answers to these questions – yes, kind of, definitely not – are immediately clear upon returning to the rural town of Mount Rose, Minnesota as the local residents prepare for the annual beauty pageant. Lorded over by Gladys Leeman (Kirstie Alley in what is easily her finest role outside of Cheers), the wife of the wealthiest man in Mount Rose, the beauty pageant is widely accepted as farce – though rarely ever openly discussed as such. With their business connections and wealth, the Leemans have ensured the pageant crown will go to their daughter, the gun-toting, Christ-loving Becky (Denise Richards). While the remaining competitors have come to accept the pageant as something to do to break up the tedium of their small-town life, Amber Adkins (Kirsten Dunst) sees it as an opportunity to pursue her seemingly lofty dreams of escaping her trailer park and becoming the next Diane Sawyer. (For the record, a chunk of my childhood was spent in a trailer park. It was called "Buckingham Place.") Amber is the complete antithesis of Becky: She lives with her single mom, Annette (Ellen Barkin), who cuts hair in their tiny trailer to earn a meager living while Amber supplements their income as a makeup artist at the local morgue. Amber's talents are readily apparent – she can tap-dance like no one's business and she's got more brains in her head than Mount Rose knows what to do with – but Becky has the advantage in at least one crucial area: Privilege. (Not to mention a murderous streak inherited from her deranged mother.)
This is where Drop Dead Gorgeous separates itself from similar teen comedies of the era. Amber's arc is a keenly relatable one for many viewers who were also lacking wealth, privilege, and the opportunities afforded by both. It's unlikely that someone like Amber – despite her intentions and commitment to academic excellence – would have an easy time continuing her education beyond Mount Rose high school. College is for people with money and connections, not for the daughters of single parents with drinking problems. Of the film's cinematic peers, She's All That is the only other teen comedy featuring a relatable female lead (choreographed school dance aside), what with Rachel Leigh Cook's dead mom and her well-meaning but oblivious suburban dad who cleans pools for the parents of the school's more wealthy and popular teens. But Drop Dead Gorgeous – and Lona Williams' script – takes this a step further with its rural setting; a small town filled with small-minded people, where a vague sense of hopelessness permeates everything like a familiar fog.
All of which makes the film sound like kind of a bummer – it's not. Drop Dead Gorgeous is easily the funniest of the late ’90s/early ’00s teen comedies, its sublime dark comedy delivered by a pitch-perfect cast: Amy Adams as the stereotypical "hot girl" cheerleader who's only participating in the pageant to validate her boyfriend's boner; the late, great Brittany Murphy as the dark horse who lives in the shadow of a very obviously gay brother who spends his nights doing Liza Minelli drag in New York; a then-lesser-known Thomas Lennon as the film's unseen "documentarian"; Ellen Barkin as Amber's beer-guzzling trailer park mom and Allison Janney as her foul-mouthed, horned-up BFF, Loretta – only those who had never seen Drop Dead Gorgeous were surprised by her Oscar-winning turn in I, Tonya. The rest of the ensemble is populated with beloved character actors like Sam McMurray, Mike McShane, Matt Malloy, Will Sasso, Mo Gaffney, and Nora Dunn – all of whom have standout moments among a cast of total standouts.
There are few moments more hilarious, however, than the return of reigning Mount Rose queen Mary Johanson (Alexandra Holden), who developed an eating disorder in the months that followed her victory. Mary makes her shakily triumphant return to the stage for an encore performance of the talent that helped her win the title: Lip-syncing to "Don't Cry Out Loud" by Melissa Manchester while a nurse pushes her around in a wheelchair. It is, in a word, glorious:
It's difficult to pinpoint a singular uproarious moment in a film that has so many: The beer can that becomes grafted onto Annette's hand after a fire breaks out in her trailer; Becky performing "Can't Take My Eyes Off Of You" while dancing with a stuffed Jesus on a cross; literally everything that comes out of Allison Janney's mouth. But beneath all the dark humor is a familiarity that makes the film's comedic beats all the more hilarious, whether or not you've ever lived in a trailer park.