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Jesus loves winners: 20 fascinating facts about cult comedy ‘Drop Dead Gorgeous,’ a problematic fave

By Lee Meyer

Everybody loves a good success story—but we love an underdog even more.

Drop Dead Gorgeous, a 1999 mockumentary directed by Michael Patrick Jann, was initially a certified flop—both with critics and at the box office. A violent, darkly comical look at small-town beauty pageants, the film stars Kirsten Dunst as Amber, a girl who yearns to win the local pageant and use the scholarship money to leave her humble hometown behind. But things quickly turn deadly as her fellow contestants start dropping like flies.

Oh, and along the way, a murderer’s row of scene-stealing actresses turn up, each as sidesplittingly hilarious as the last, including Allison Janney, Kirstie Alley, Denise Richards, Brittany Murphy, Ellen Barkin, and even Amy Adams.

Drop Dead Gorgeous didn’t hit at first, but thanks in part to its iconic ensemble, the movie has since developed a devoted cult following—even if a few of its story elements are problematic by todays’ standards.

As we approach the film’s 25th anniversary, here are 20 facts about the strange, hilarious and off-kilter comedy.

1. The film flopped at the box office…

Image Credit: ‘Drop Dead Gorgeous,’ New Line Cinema

Even though has a modest production budget of $15 million, it was considered a box-office bomb, only grossing $10.5 million in total during its theatrical run.

2. …and was panned by critics.

Image Credit: ‘Drop Dead Gorgeous,’ New Line Cinema

Reviews were not kind to the film at the time, and though some critics have praised it in retrospect, the film still sits at a poor 47% approval rating on the review aggregator site Rotten Tomatoes.

3. It’s based on screenwriter Lona Williams’ upbringing.

Image Credit: ‘Drop Dead Gorgeous,’ New Line Cinema

After working as a writing assistant on The Simpsons, Lona Williams wrote her first feature screenplay—initially titled Dairy Queens—based on her own experiences participating in beauty pageants while growing up in Minnesota.

4. Like Amber, Williams was a runner-up, but got to leave her small town.

Image Credit: ‘Drop Dead Gorgeous,’ New Line Cinema

Williams used scholarship money from pageants to go to the University of Minnesota.

5. Its cult status surprised everyone involved.

Image Credit: ‘Drop Dead Gorgeous,’ New Line Cinema

Janney told Buzzfeed, “My funniest moment about Drop Dead Gorgeous was being in an airport and sitting next to some kids who were going over their favorite Loretta lines… and I said, ‘Um, hi, I played Loretta in the movie.’ And they literally started screaming. It was really funny. I feel like a rock star being part of that movie.”

6. The dark script was a turn-off for some producers.

Image Credit: ‘Drop Dead Gorgeous,’ New Line Cinema

“It was really dark. I kind of forgot,” Williams told Buzzfeed in a 2014 oral history of the film. “That’s what’s funny… It’s not for everyone.”

7. Williams initially wanted to hire unknown actors, a la The Blair Witch Project.

Image Credit: ‘Drop Dead Gorgeous,’ New Line Cinema

You can see the vision, especially in moments where the characters address and talk to the camera. But imagine if Janney, Alley, Richards, and Dunst weren’t in the movie?

8. Williams also wrote the flop Sugar & Spice, but is credited with the pseudonym Mandy Nelson

Image Credit: ‘Sugar & Spice,’ New Line Cinema

Sugar & Spice was a similarly dark teen comedy, one that followed a group of high school cheerleaders who turn to crime when one of their members becomes pregnant and desperate for money. It was also—similarly—a box office bomb, only grossing $16.9 million when it hit theaters in 2001.

9. Jann envisioned the movie as a piece of counter-culture.

Image Credit: ‘Drop Dead Gorgeous,’ New Line Cinema

“This is for the girls who went to Clueless and were like, f— them,” the director once said.

10. The film marks Amy Adams’ debut.

Image Credit: ‘Drop Dead Gorgeous,’ New Line Cinema

The future six-time Oscar nominee has a small part in the film as the sweet, fellow pageant contestant Leslie Miller. She was performing in a dinner theater ensemble at the time she auditioned and got the gig—her very first on-screen role.

11. The film’s failure led to Jann turning away from directing feature films.

Image Credit: ‘Drop Dead Gorgeous,’ New Line Cinema

Though Jann has been a prolific television director in the ensuing years—helming episodes Crazy Ex-Girlfriend, Superstore, Community, Reno 911!, and more—his 2023 Western horror Organ Trail was his first theatrical film since Drop Dead Gorgeous.

12. Its darkness, while a turnoff for critics and viewers during its initial release, is one of the reasons for its queer cult following.

Queer director Darren Stein—whose own films like Jawbreaker have cult followings—told Buzzfeed: “I think all cult movies have something that’s intrinsically transgressive about them. They go to a place that regular studio films don’t go to that’s usually darker, edgier, and more forbidden.”

13. The movie celebrates the weirdos in high school.

Image Credit: ‘Drop Dead Gorgeous,’ New Line Cinema

“People have dark fantasies in high school, and as an adult, they can actually live out those fantasies in a cinematic form,” Stein told Buzzfeed.

14. Drag queen Peaches Christ screened the movie at her midnight movie series in San Francisco.

Photo Credit: Getty Images

She told Buzzfeed: “In the old days, a cult movie found its audience on the midnight movie circuit, like Pink Flamingos or Eraserhead. In the last 20, 30 years, with home video and cable television, a lot of these cults are built in people’s living rooms… I think Drop Dead Gorgeous is the perfect example of that.”

15. Peaches Christ thinks the movie was marketed to the wrong audience.

Image Credit: ‘Drop Dead Gorgeous,’ New Line Cinema

“It was for urban queers,” she told Buzzfeed, noting that New Line Cinema marketed it for all teens.

16. The movie may have inspired Gilmore Girls!

Image Credits: ‘Drop Dead Gorgeous,’ New Line Cinema (left) | ‘Gilmore Girls,’ Warner Bros. Television (right)

It’s been said that TV producer Gavin Polone pitched the idea of a series about a mother and daughter who are close in age—inspired by Amber and Annette in Drop Dead Gorgeous—to eventual Gilmore Girls showrunnerAmy Sherman-Palladino.

18. It wasn’t available to stream until 2019.

Image Credit: ‘Drop Dead Gorgeous,’ New Line Cinema

Hulu acquired streaming rights to coincide with its 20th anniversary, thus introduced introducing the film to a new legion of fans.

19. There’s even a gay character!

Image Credit: ‘Drop Dead Gorgeous,’ New Line Cinema

In his only credited screen role ever, Jamie Olsen plays Peter, the gay brother of Brittany Murphy’s Lisa Swenson. Lisa is sweetly supportive of her brother and his burgeoning drag career in NYC… though she also outs him to her dad!

20. Adam White of The Independent summed it up perfectly.

Image Credit: ‘Drop Dead Gorgeous,’ New Line Cinema

Writing in 2019, on the occasion of the film’s 20th anniversary, White said, “Drop Dead Gorgeous, the cult beauty pageant comedy that turns 20 today, was made for a generation of freaks and outsiders, whose ambitions, oddities, queerness and poverty were otherwise ignored by anything similarly mainstream or funny.”

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