‘Drop Dead Gorgeous’ at 25: Denise Richards and More on How the Very Un-P.C. Mockumentary Became a Cult Classic

“Don’t Cry Out Loud,” lip-syncs Mary Johanson (Alexandra Holden), the reigning Mount Rose Teen Princess, with the few ounces of energy she has left after the pressures of pageantry have withered her away.

The equally hard-working cast and crew of “Drop Dead Gorgeous” would benefit from the wise words of said Melissa Manchester hit, written by Peter Allen and Carole Bayer Sager in 1976, when the film debuted in 1999. And way outside the box office top 10 in a crowded movie summer already filled up by “American Pie” and “The Blair Witch Project,” and without recouping its $15 million budget. Mild for the time, but by today’s standards huge for a female-driven comedy about high schoolers clawing over each other for the top spot in a Minnesota-statewide pageant.

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Written by Lona Williams (who also moonlights onscreen as the pageant’s timid Judge #3), director Michael Patrick Jann’s cult classic mockumentary follows a Los Angeles documentary crew who descend upon the small town of Mount Rose, where all that’s paramount is gearing up for the Sarah Rose Cosmetics American Teen Princess Pageant. But someone’s holding a grudge against the contestants, who are being mysteriously killed off, and the crew’s footage is about to catch all the murder and mayhem. The eventual big night is just the beginning of the madness — including a climactic, massive spell of food poisoning.

The killer female-led ensemble included Kirsten Dunst, Ellen Barkin, Kirstie Alley, and Denise Richards as rival mother-daughter duos from opposite sides of the tracks. The cast list goes on — Allison Janney, Brittany Murphy, and also, in her film debut, a then-unknown named Amy Adams. Despite the star power, the poorly reviewed dark comedy faded into obscurity fast, but not before underdog fans could fall in love with its inappropriate, tacky awesomeness.

“Drop Dead Gorgeous” was ahead of its time, well before comedy mockumentaries became a staple genre in film and TV. No walk of life is safe from ridicule here, and not even the lord Jesus himself as Becky Leeman’s (Richards) outrageous pageant performance proves. All of the film’s problematic elements — with crass, politically incorrect humor that leaves no corner of the population unscathed — could possibly have an argument made for their defense.

DROP DEAD GORGEOUS, Mindy Sterling, Kirsten Dunst, Denise Richards, 1999. ©New Line Cinema/ Courtesy Everett Collection.
‘Drop Dead Gorgeous’: Mindy Sterling, Kirsten Dunst, Denise Richards, 1999. ?New Line Cinema/ Courtesy Everett Collection.?New Line Cinema/Courtesy Everett Collection

Like Amber (Dunst), the story’s Diane Sawyer-worshipping hero who hangs in there against all odds while dreaming of becoming a news anchor, this antithesis to the common teen fare of the time only later got its due. And in the case of “Drop Dead Gorgeous,” on home video, repertory midnight screenings, and even in a live parody show starring drag superstars Peaches Christ and Jinkx Monsoon. “Drop Dead Gorgeous” is iconic now thanks to the queer folks and film lovers who’ve helped resurrect it, an audience that perhaps wasn’t there (or encouraged to be so) when the film ultimately grossed $10 million by the end of its run.

Timed to the film’s anniversary — “Drop Dead Gorgeous” opened in theaters on July 23, 1999 from New Line Cinema — IndieWire spoke with director Michael Patrick Jann and stars Denise Richards and Mindy Sterling (who plays stressed-out pageant organizer Iris) about the ever-growing but still very punk-rock legacy of “Drop Dead Gorgeous.”

This interview has been condensed and edited for clarity.

IndieWire: When did you realize “Drop Dead Gorgeous” was becoming a cult favorite and thus softening the blow of its failure to launch upon release?

Michael Patrick Jann: I had an inkling. I would hear from people every once in a while just like, “Oh my god. I love that movie,” from people of a particular age who were the people that the movie was really made for. Specifically, the movie was made for outsider kids. When I first went to pitch it at New Line, my pitch was: “This is for everybody who saw ‘Clueless’ and was like ‘fuck them’!”

Denise Richards: A few years ago, I brought my daughter, Lola, to the Hollywood Forever Cemetery Cinespia and introduced her to “Drop Dead Gorgeous”. It was a proud moment for me having my daughter there […] I had one of the best times filming “Drop Dead Gorgeous.” I love that, over the years, fans still love the movie. I think it was also before its time before social media and reality television.

Mindy Sterling: Nobody knew where it was going to go, but we all thought it was very magical. I was so honored to have gotten to be a part of this and that it still lives and people still ask about it. People go crazy when I do my [conventions]. They go, “Oh my god, you were in that!” and I love that feeling. At the time, not all the women in the cast were that big or successful, but look at them now. To me, that’s saying something. I remember sitting on the grass and talking to Amy Adams about how driven she was. I said, “Oh honey, you have to go to LA.”

DROP DEAD GORGEOUS, Ellen Barkin, Allison Janney, Kirsten Dunst, 1999. ©New Line Cinema/ Courtesy Everett Collection.
‘Drop Dead Gorgeous’: Ellen Barkin, Allison Janney, Kirsten Dunst, 1999. ?New Line Cinema/ Courtesy Everett Collection.?New Line Cinema/Courtesy Everett Collection

Were you surprised that it’s a heavily recognized film in the queer community? 

Jann: I think it’s fantastic. At the time that it came out, especially in big city newspapers, it was not well reviewed. Older critics didn’t get it, [it] 100% flew right over their heads. This movie isn’t for those people. It’s a teen movie about beauty pageants, but it’s a pretty punk rock movie. It’s not for the Roger Eberts of the world.  One of the things that’s so gratifying about the movie getting its due is because of the diversity that has come to media. Those voices didn’t have a platform. My good friend Kevin Allison [aka The Red Head Gay from “The State”] said it’s shocking that of the two of us, you have done the thing that is so prominent in queer culture.

What prior mockumentary experience did you have as a viewer or creator?

Jann: I’d been doing it for years on TV and, also I was aware that “Drop Dead Gorgeous” is a different kind of mockumentary than Christopher Guest’s. The format of the Chris Guest films is that they’ve got all these great improv actors and super funny people. Especially “Spinal Tap,” part of the ethos of it is like, “Let’s be loose enough that these people can be funny. Let’s get out of the way.” There’s a mix of written [dialogue], but there’s so much improv going on, and that’s part of the fun of those movies. “Drop Dead Gorgeous” is not that mockumentary. There’s improv in it but it’s not on-camera. There are things in it that we figured out on the way or in rehearsal. It’s meticulously framed and very conscious as to where it goes back and forth from being a proscenium, perfect little frame to a little more handheld. Those edits bump into each other very deliberately to create friction between the two different styles.

Organized chaos. 

Jann: We did come up with a lot of jokes on the set, like Allison Janney came up with tons of her material. She was a delight to work with. She’s so phenomenal. I cast her off a tape. The second I saw it, I was just like, “Her!” The character was fully realized right off the bat.

The cast has since lost Brittany Murphy and now Kirstie Alley. Can you share any fond memories of working with either of them?

Jann: Kirstie was fantastic. She’s iconic, She was really great to work with. She showed up. There was a little bit of like, ya know, in the first couple days, because she was a big enough star that she didn’t really want to come and rehearse beforehand, so we had to be like, “No, no, you’re being too nice. Underneath your Minnesota nice needs to be like a steeliness. People need to be afraid of you.” And Brittany always showed up ready to go [and] gave 100% on each take. Brittany was a walking ball of warmth and love on the set. She had that big laugh. She was easy for all the actors to work with because she was giving all the time. She was a delight.

DROP DEAD GORGEOUS, from left: Denise Richards, ?, Brittany Murphy,  Kirsten Dunst, Amy Adams, 1999, © New Line/courtesy Everett Collection
‘Drop Dead Gorgeous’: Denise Richards, Laurie A. Sinclair, Brittany Murphy, Kirsten Dunst, Amy Adams, 1999, ? New Line/courtesy Everett Collection?New Line Cinema/Courtesy Everett Collection

There’s nothing better than when her character Lisa Swenson screams, “GAY!”

Jann: She’s an ally. There’s no question about it.

Denise Richards: I remember Brittany Murphy being a beautiful ray of light that lit up any room she walked into. And I feel so blessed to have had Kirstie Alley play my mom in that movie.

Mindy Sterling: Kirstie was really funny and very sweet. Brittany was such a wonderful soul. I remember when I left, she bought me this sticker that I put on my bedroom door that said “Goddess,” and I was really touched. Everybody loved her. It was such an amazing group of people. It was like a family.

All these years later the film is still fresh and just as controversial. Do you think “Drop Dead Gorgeous” is protected against the “cancel police”? I’m glad we’ve arguably got to a better place with respecting sensitive topics like the use of the “R” word for instance. How does that sit?

Jann: I think that it’s of its time in that aspect. For me, if anybody is hurt by it, it just wasn’t something that people thought about. That would be something that, were I given the chance, I would do differently. It’s not meant maliciously, but it is the one piece of the movie I would change.

Or the past contestant with an eating disorder? Funny in a grim way.

Mindy Sterling: That is how important this was [to her]. They’re nobody if they’re not trying to be queen or get that special prize. You don’t know what happens when they don’t get it. Maybe they have a nervous breakdown and want to kill everybody [like Gladys, Kirstie Alley’s character]. Back then, think about that. That is what went on, especially in small towns and probably still does a little bit […] I love when people [like screenwriter Lona Williams, who had pageant experience as a child] have something that is so different that we don’t know about, and it’s like, “This is what I went through.” It has more meaning because it’s coming from a real place.

Let’s talk about Becky’s (Denise Richards) dance with Jesus.

Jann: That’s one of my favorite parts. She was great, too. She really jumped in with both feet in an area that was not her specialty. She was upfront about it that she’s not a comedian. We came up with a way for her to work with her strengths. One of the things I asked her to do was to work on it as if she were auditioning to be a newscaster. That’s one of the key sort of things to her performance.

Richards: When I read the scene where my character had to chance with Jesus, I really wanted to play the scene real, which meant playing Rebecca as being very religious but not making fun of or mocking anything. I played Rebecca believing her story, having nothing to do with anyone else.

DROP DEAD GORGEOUS, Mindy Sterling (obscured), Kirstie Alley, Denise Richards, Sam McMurray, 1999. ©New Line Cinema/ Courtesy Everett Collection.
‘Drop Dead Gorgeous’: Kirstie Alley, Denise Richards, Sam McMurray, 1999. ?New Line Cinema/ Courtesy Everett Collection.?New Line Cinema/Courtesy Everett Collection

Mindy, you did double duty in the summer of 1999 as the sidekick to a lunatic — Frau Farbissina to Dr. Evil (Mike Myers) in “Austin Powers: The Spy Who Shagged Me” — and, of course, as the much less menacing Iris to Gladys Leeman in “Drop Dead Gorgeous.” Who was crazier: Gladys or Dr. Evil?

Sterling: [Laughs.] Oh wow, that’s a tough one. They both have their crazy, sick moments. Poor Iris.

Had you played around with your accent before filming? 

Sterling (snapping back into her Minnesotan dialect to answer this): Oh yah, oh yah. We really went to the top of that. There was this one woman who was a local. We always went to her, like, “How do you say this?” or “Say this line,” and she goes, “I don’t know why everyone’s asking me because I don’t have an accent.” And I’m like, “ummm…”. Kirsten was great [at it] too. She loved that part, loved talking like that.

I’m so happy the film is finally on Blu-ray, but once again, it’s virtually nowhere to be found on streaming. Does that disappoint you?

Jann: Initially, I was kind of like, oh it’s a bummer it’s not available all the time to watch, but on the other hand, I’m like, you know what? I don’t think this movie should be available all the time to watch. I’ve grown to love that it’s got that kind of, like, what used to be [on] when I was a kid, the “Charlie Brown” special is on, and it’s on once a year, you have to find it and go to it. This is a movie that every once in a while shows up. It’s a very cult movie, and it never was intended to be anything other than that. This is the right way for this to live. When it first came out and it wasn’t a giant success, it was hurtful to me, so I’m very gratified that, 25 years later, people still care about it. It has found its correct audience. I appreciate all the people who understand it. There’s a small sense of brotherhood and sisterhood, family, of the people who can appreciate the darkness and the light.

The final shot of Amber, Kirsten Dunst’s character, is such a joyous moment as Joan Jett proclaims on the soundtrack, “You’re gonna make it after all.”

Jann: I’m glad you took it that way. It’s certainly intended to be joyous and awful. She literally stepped over somebody’s corpse, but she did it, and that push-in shot, the logo for the TV station, is specifically designed with that star, so when it pushes in on her […] it’s corny, but it’s a star halo, and that’s the last image of the movie.

Sterling: Yeah, just don’t kill yourself if you don’t get something because life goes on, and bigger and better stuff comes to you. 

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