On-Set Feuds, Offended Audiences and a Box Office Disaster: 20 Secrets You Might Not Know About Drop Dead Gorgeous

Released on July 23, 1999, Drop Dead Gorgeous launched the career of Amy Adams, who made her movie debut, and might've inspired an iconic series

By Tierney Bricker Jul 23, 2019 10:00 AMTags

Jesus loves winners. and 20 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, 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. And while it's gone on to become a beloved cult classic over the years, ridiculously quotable and full of before-they-became super-famous stars, Drop Dead Gorgeous was a box office disaster and critic punching bag when it came out 20 years ago in the middle of the teen comedy gold rush that was 1999. It wasn't  the most popular, sure, but it was one of the "most smartest" and was way ahead of its time. 

On-Set Feuds, Offended Audiences and a Box Office Disaster: 20 Secrets You Might Not Know About Drop Dead Gorgeous

Made for just under $15 million, Drop Dead Gorgeous grossed just $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 20th anniversary, here are some secrets you might not know about Drop Dead Gorgeous...

1. Drop Dead Gorgeous was based on screenwriter Lona Williams, a former Minnesota beauty contestant herself, experience in the world of local pageants. When the film initially bombed at the box office and received some harsh reviews at the time, 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, because there was so much of myself in this," she admitted.

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 asshole," 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 would never direct another feature film, 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."

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 aka paid less than a speaking role.)

4. The movie was originally supposed to be called Dairy Queens. However, the corporate 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. 

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. The Sabrina the Teenage Witch star 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."

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. For Amber's supportive and beer-loving mom, Goldie Hawn was initially approached ("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. 

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, and revealed this about her first day of filming introduction: "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 she refused to wear many 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.

8. DDG marked Amy Adams' feature film debut, with the star going on to receive six Oscar nominations. And from the start, everyone on set knew Adams, who played the 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,'" Janney 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.  "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.'"

9. While she would go in to become a TV icon thanks to The West Wing and win an Oscar in 2018 for her work in I, Tonya, Janney 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 HuffPo 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."

9. Now comfortable with ad-libbing, Janney revealed she only ad-libbed one time in Drop, Dead Gorgeous, but it's a moment she's rather proud of. "The one ad-lib I said that I was proud of was 'I got some!'" she told the Huffingtong 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 the 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."

10. While she's gone on to become one of the most famous and 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 Emmy-winning 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."

11. 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."

12. In one of the film's most iconic scenes, 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 done in cult cinema history, but some of the extras who were on set the day the performance was filmed were not amused. 

"Halfway through my performance they were offended and actually walked off the set and left," The Real Housewives of Beverly Hills star told VH1 of the unprepared audience members. 

13. 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, finding an audiences years later while 10 Things, She's All That, American Pie and Jawbreaker and more were credits for ushering in the golden era of the genre.

14. Williams' less-than-great experience on Drop Dead Gorgeous was followed up by 2001's Sugar & Spice, the cheerleader-turn-into-bank robbers dark comedy, which she ultimately took her name off of after massive changes 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.

15. Janney revealed her adorable nickname for Dunst during an interview reflecting on the filming experience, telling Huffington Post, "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." 

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. It took me a while. I was like, That sounds familiar,'" she told HuffPo. "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."

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 the Japanese movie-goers. The popular pop star ended up in a very small role as the sister of contestant Molly Howard.

18. Perhaps take this with a few grains of salt from a shaker at Luke's Diner, but Gavin Polone, one of the producers alleged to 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.)

19. While the film's ending is already pretty dark, the original ending 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."

20. 20 years after working together on Drop Dead Gorgeous as BFFs Annette and Loretta, Barkin and Janney are reuniting on-screen in the 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 Instagram post. "First time was #DropDeadGorgeoustogether again in #breakingnewsinyubacounty More full circles coming!"

Drop Dead Gorgeous is available to stream on Hulu.