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    Shocking Secrets About Drop Dead Gorgeous Revealed

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    Jesus loves winners. And 27 years later, we still love Drop Dead Gorgeous. 

    In the latest movie anniversary to make you truly feel the harsh, cruel and unjust passing of your youth, we’re here to remind you that Drop Dead Gorgeous—the beauty pageant satire starring Kirsten Dunst, Denise Richards, Kirstie Alley and Ellen Barkin—came out on July, 23, 1999. 

    The dark teen comedy, written by former beauty pageant queen Lona Williams and directed by Michael Patrick Jann, was like if Miss Congeniality and Heathers had a baby that grew up and went through a goth phase.

    It’s gone on to become a beloved cult classic over the years, chock full of ridiculously quotable lines and before-they-became super-famous stars (hi, Amy Adams, Brittany Murphy and Allison Janney). But Drop Dead Gorgeous was a box office disaster and critic punching bag when it came out in the middle of the teen comedy gold rush that was 1999.

    And, sure, it wasn’t the most popular, but it was one of the “most smartest” and was way ahead of its time. 

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    Made for just under $15 million, Drop Dead Gorgeous grossed $10.5 million when it hit theaters, earning just 46 percent fresh on Rotten Tomatoes from critics.

    Entertainment Weekly gave it a D, calling it “graceless,” while the late Roger Ebert said, “Sometimes I wonder how anyone could have thought a screenplay was funny enough to film.”

    Kimberly Wright/New Line/Kobal/Shutterstock

    Ding, fried it up!

    But against all odds, Drop Dead Gorgeous became a cult classic, an underrated dark comedy that could only be truly appreciated years later.

    But even before the harsh reviews and disappointing numbers, it wasn’t exactly smooth sailing on the set, with clashes going down between the young writer and director, and one of the stars exhibiting some diva tendencies. 

    Plus, did you know one mega A-lister made her acting debut in Drop Dead Gorgeous? And that Gilmore Girls is rumored to have taken inspiration from the film?

    In honor of its anniversary, here are some secrets you might not know about Drop Dead Gorgeous…

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    1. Drop Dead Gorgeous was based on the experiences screenwriter Lona Williams—a former Minnesota beauty contestant—had in the world of local pageants. When the film initially bombed at the box office and received some harsh reviews, Williams, who had won a college scholarship after taking home the title of Minnesota’s Junior Miss, felt defeated. “It was so hurtful on a deep level,” she admitted, “because there was so much of myself in this.” 

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    2. Even before the bad reviews and box office woes, Williams didn’t have the best experience on-set, often clashing with first time director Michael Patrick Jann. “I just found [Jann] to be a bit of an a–hole,” she recalled to Buzzfeed. “I remember going out in the rain, crying, going to my rental car, like, having a full body cry because I felt like, Oh my god, this could get away and not turn out the way I see it. There were a couple things like that, and then I pulled myself together…I really didn’t favor him.”Jann, who wouldn’t direct another feature film until 2023’s Organ Trail, admitted, “I think I probably could have been nicer. As a 26-year-old, I was probably a little more like, ‘No, we’re f–king doing it this way. What are you talking about?’ I was maybe a tiny bit insensitive at that time in my life.”

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    3. Another disappointing experience for Williams was when she was allegedly told by a producer she was “too old” to make a quick appearance in the film as a candy striper, and was instead told she could make a cameo as Jean, the non-speaking third pageant judge. (No lines means you are considered a featured extra, i.e. paid less than a speaking role.)

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    4. The movie was originally supposed to be called Dairy Queens. However, the corporation that owns Dairy Queen allegedly didn’t love that idea or the association with the mockumentary-style dark comedy, so they filed a lawsuit and Drop Dead Gorgeous became the title. 

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    5. Before Kirsten Dunst landed the lead role of Amber Atkins, the pageant queen with dreams of becoming the next Diane Sawyer, then reigning teen queen Melissa Joan Hart auditioned for the part. But the Sabrina the Teenage Witch lead ended up starring in Drive Me Crazy, a teen rom-com that came out a few months later.When it came to casting Dunst, it wasn’t the young actress’ breakout roles in Interview With a Vampire or Jumanji that convinced Jann she could play Amber; it was Celebrity Teen Jeopardy.“She was so sweet and so normal, and so guileless,” he said. “That’s the girl who can grab the microphone out of the dead reporter’s hand and joyfully keep reporting with no guile. There’s no evil in her. There’s no premeditation…for someone who’d been in movies since she was a kid, like a tiny, tiny kid…she was at ease with being ill at ease, which was charming to me.”

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    6. While it’s hard to imagine anyone else starring as Annette Atkins and Gladys Leeman aside from Ellen Barkin and Kirstie Alley, neither were the first choice for their respective roles. Goldie Hawn was initially approached to play Amber’s supportive and beer-loving mom (“I think she would have been less dirty,” Jann told Buzzfeed), while Sigourney Weaver was the studio’s top choice for the ultra-competitive and ultimately murderous Gladys. 

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    7. “It was my introduction to, ‘Oh, that person’s a huge f–king star.'” That’s how Jann described his experience on-set with Alley to Buzzfeed, revealing this about her first day of filming: “She gets up there and she announces that she’s just quit smoking, she’s on a diet, and she’s got her period. And she’s not f–king kidding.”He went on to allege the actress, who died in 2022, refused to wear many of the costumes the wardrobe department had picked for Gladys, instead asking for the outfits to be sent to the Scientology Celebrity Centre in Hollywood to try them on there.

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    8. Drop Dead Gorgeous marked Amy Adams‘ feature film debut, with the star going on to collect six Oscar nominations, the most recent for 2018’s Vice. And from the start, everyone on set knew Adams, who played promiscuous cheerleader Leslie Miller, had something special. “I remember Amy coming in, and immediately I was like, ‘Well, that’s it, she’s got that part,'” Allison Janney (who played Annette’s bestie Loretta) told BuzzFeed. But funnily enough, Janney forgot that they were both in the movie when Adams later guest-starred on Janney’s hit TV series The West Wing in 2002. “We were filming in Pittsburgh and we went out to dinner together and she was like, ‘Do you remember I was in [Drop Dead Gorgeous]?'” Janney recalled with a laugh to VH1.In an interview with Cinema Blend, Adams said, “That was my first movie I ever made! Everything about that movie was just so surreal to me. That was the first time I realized like, ‘I think I could go to Hollywood and at least get some commercials or something.'”

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    9. While her seven-season run on The West Wing would net Janney four of her seven Emmys and she’d go on to win an Oscar in 2018 for I, Tonya, the actress ended up getting to audition for the movie thanks to the late Brittany Murphy, who was first cast as contestant Lisa Swenson.”I had just done A View From the Bridge on Broadway with Brittany Murphy,” Janney told the Huffington Post of the Clueless star. “John Papsidera cast Drop Dead Gorgeous, because I think Brittany auditioned for the movie and told him he needed to cast me in it, if I’m not crazy.”

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    10. Now comfortable with ad-libbing, Janney revealed she only went off script once in Drop, Dead Gorgeous. “The one ad-lib I said that I was proud of was ‘I got some!'” she told the Huffington Post. “That was my one ad-lib because I don’t think I knew how to ad-lib at that point in my career.” Janney did have a hand in establishing Loretta’s look, however, including her over-the-top orange tan.”Maybe her neck would be a different color than her face. And then we discussed that her idea of glamour might not be everyone’s,” she said. “She might wear blue eye shadow with bright red lipstick. She definitely has a confused sense of glamour, a trailer park-tinged sense of glamour.”

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    11. While she’s gone on to become one of the most successful alums from the movie, Janney wasn’t invited to the Drop Dead Gorgeous premiere in 1999.”I was not even included in the poster on that. They usually don’t ask you if you’re not included on the poster,” the Mom star explained. “Because then they have to pay for you to get there, and that involves money for the studio to pay, so of course they’re not going to want to pay for everyone in the movie to come. I understand that.”

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    12. Matt Molloy played John Dough, the local pageant judge with an inappropriate level of interest in the young contestants. And the role has earned him some less than ideal fan encounters over the years.”Six times in my life I have been in a public setting—once in a mall, once in a bakery, each time with a lot of people around—and a teenage girl has turned and yelled, ‘You’re the pervert!'” he told Buzzfeed. “And I put my hands up and say, ‘In a movie. In a movie. Finish the sentence.’ But there’s this moment where the whole fucking place turns, and it’s just like, Oh, you’re hanging by your balls, kid. That still happens.”

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    13. In one of the film’s most iconic scenes, Denise Richards‘ mean rich girl Becky performs a tone-deaf (in more ways than one) rendition of Frankie Valli’s “Can’t Take My Eyes Off of You” while dancing with a Jesus doll on a crucifix. The scene has gone down in cult cinema history, but some of the extras who were on set when it was filmed were not amused. “Halfway through my performance they were offended,” The Real Housewives of Beverly Hills alum told VH1, “and actually walked off the set and left.”

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    14. Of course, there was another iconic cover of the Valli hit that came out in 1999: Heath Ledger‘s high school bleacher rendition in 10 Things I Hate About You. The dueling performances’ mainstream vs. cult success is symbolic of Drop Dead Gorgeous‘ legacy among 1999’s teen comedy offerings. While the dark comedy eventually found its audience years later, 10 Things, She’s All That, American Pie and Jawbreaker were among the films credited with ushering in the golden era of the genre.

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    14. Screenerwriter Williams’ less-than-great experience on Drop Dead Gorgeous was followed up by 2001’s Sugar & Spice. She eventually took her name off the cheerleaders-turned-bank robbers dark comedy after massive alterations were made to the script following the 1999 Columbine school shooting, including a change to the original title (Sugar & Spice & Semi-automatics). The credited writer is the non-existent Mandy Nelson.

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    15. Janney revealed her adorable nickname for Dunst during her chat with Huffington Post, telling the outlet, “I had a lot of fun getting to know Kirsten, or Kiki, as they called her on the movie—I don’t know what they call her now.” She described Dunst, Richards, Murphy and Adams as “just really sweet, lovely girls.” 

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    16. Believe it or not, given her impressive resume, Drop Dead Gorgeous is the project most fans approach Janney about. “I think I get more people coming up to me saying how much they love that movie than any other thing I’ve done,” she told The A.V. Club. “Even more than West Wing.”Her favorite fan encounter? “I was sitting in an airport next to these teenagers, and they were quoting lines that Loretta said,” she told Huffington Post. “It took me a while. I was like, ‘That sounds familiar.’ And then all of a sudden I realize, ‘Oh, they’re talking about Loretta.’ And then I said, ‘Excuse me, did you know that I played Loretta?’ And they started screaming and of course they had a huge photo op afterward. They really didn’t know they were sitting next to me. It was great.”

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    17. In an odd casting move, Japanese superstar Seiko Matsuda was fit into the movie after the studio, New Line, had sold the international rights to the film, and need to appeal to Japanese movie-goers. The pop star ended up in a very small role as the sister of contestant Molly Howard.

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    18. Perhaps take this with a few grains of salt from a shaker at Luke’s Diner, but Gavin Polone, one of the producers, told Buzzfeed that he found the mother-daughter dynamic explored between the close-in-age Annette and Amber in Drop Dead Gorgeous so dynamic and fascinating that he pitched the concept to Amy Sherman-Palladino, who would go on to create Gilmore Girls. “Gilmore Girls wouldn’t exist if I had not produced that movie,” Polone claimed. (Hey, we do think Lorelai and Rory would totally have watched Drop Dead Gorgeous during one of their many movie nights.)

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    19. While the film’s ending is already pretty dark, the initial version was even more twisted “In the original ending, Kirstie actually killed herself in prison,” Jann revealed to Buzzfeed. “In the next scene, there was just her feet swinging in the jail cell, and it went from her feet swinging down to an ashtray with a still lit cigarette.” Gladys’ shooting spree was then originally committed by librarian/former Mount Rose American Teen Princess Iona Hildebrandt. “The whole theater went, ‘Ugh,'” Jann said of the test audiences’ reaction to the ending. “That was too much. That was one step over the line.”

    Allison Janney/Instagram

    20. Twenty years after working together on Drop Dead Gorgeous as BFFs Annette and Loretta, Barkin and Janney reunited on-screen in the 2021 film Breaking News in Yuba County.”Ok, this is a full circle moment for me! In and out of character with the amazing #EllenBarkin,” Janney, who once described Barkin as “a dream to work with,” captioned a cute behind-the-scenes 2019 Instagram post. “First time was #DropDeadGorgeoustogether again in #breakingnewsinyubacounty More full circles coming!”

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