Hosted by Chris Winterbauer and Lizzie Bassett
Written by a model from the transcript; not yet reviewed.
This bonus episode examines the 1999 dark comedy Drop Dead Gorgeous, exploring its production history, cultural impact, and how it evolved from a box office bomb into a cult classic. The host and the guest, Hallie Kiefer, discuss the film's unique mockumentary style, its sharp critique of American meritocracy, and performances from a standout cast including Kirsten Dunst, Denise Richards, and Kirstie Alley. The conversation also highlights behind-the-scenes tensions between writer Lana Williams, director Michael Patrick Jan, and producer Gavin Pallone, tracing how a spec script based on real Midwestern pageant experiences became a beloved, anarchic satire.
The episode opens with a brief promo for Hulu’s new series and a Pluto TV ad before the hosts introduce themselves and the show’s theme.
Hallie Kiefer from Ruined is welcomed, and the hosts discuss her background and the format of her podcast.
The hosts outline the plot of Drop Dead Gorgeous, highlighting its mockumentary style and commentary on American ambition.
The episode delves into the film’s production, covering writer Lana Williams, director Michael Patrick Jan, and producer Gavin Pallone’s backgrounds.
The hosts discuss Kirstie Alley’s difficult behavior during filming, including her refusal to wear costumes and work with the dialect coach.
The episode covers the lawsuit filed by Dairy Queen to force a title change from Dairy Queens to avoid trademark conflict.
The discussion turns to the original ending where the lead dies by suicide, and how it was altered for a lighter tone.
The hosts analyze the film’s poor opening weekend, low total gross, and negative reviews comparing it to other mockumentaries.
The conversation shifts to how the movie gained a cult following via home rentals and later streaming platforms.
The hosts discuss Lana Williams’ subsequent writing projects, her pseudonym use, and the challenges of getting a feature produced.
The episode concludes with a hopeful look at reviving campy, queer‑friendly comedies and encouraging writers like Williams.
Real-Life Small Town Pageantsstory
The writer Lana Williams based the script on her own 1985 experiences competing in Minnesota pageants as a junior in high school, using the competition as a vehicle to escape her small town.
The State Troupe Originsinsight
Director Michael Patrick Jan emerged from NYU comedy troupe The State, whose MTV sketch show faced network interference and cancellation before members went on to create projects like Reno 911.
Writer Lana Williams recalled crying in her rental car due to creative friction with first-time feature director Michael Patrick Jan during the tense production.
Amy Adams Debutdata
Amy Adams was cast as a local hire from Minneapolis during her time dancing at dinner theaters and working extra shifts at Hooters.
Dairy Queen Trademark Lawsuitstory
The film was originally titled Dairy Queens, but American Dairy Queen sued the production to force a title change, fearing association with the movie's unwholesome content.
Box Office Bombdata
Released against heavy summer competition like American Pie and The Blair Witch Project, the $15 million film debuted at number 12 and earned only $10 million during its theatrical run.
Cult Classic Re-emergenceinsight
The film found a second life and venerated camp status through repeated home rentals by bored teenagers, particularly female and queer audiences.
“I made the mistake of thinking that, you know, maybe it was like a little bit of a bit for the show that she was unable to watch these movies.”
“I think the secret of mine and Alison's success, it is that she's not really not a horror person.”
“The one that upon this re-watch, I was just like, this was completely unnecessary and honestly not funny is the American girl who is adopted by the Japanese family.”
“She was so funny and she's so funny in this.”
“She actually had her clothes sent to the Scientology Celebrity Center in Hollywood and she would try them on there.”
“On a budget of around $15 million, it debuted at number 12 and took in only $3.9 million its opening weekend. It earned only about $10 million during its entire theatrical run.”
“In 2019, it finally hit streaming. It was eventually picked up by Revry, which is an LGBTQI plus streaming service who reported it was their top title.”
“The transformation of Drop Dead Gorgeous from a flop to a venerated artifact of Y2K era camp began with bored teenagers, most of them female and/or queer, who flocked to blockbusters around the country and rented the movie over and over.”
‘Drop Dead Gorgeous’ was supposed to be a big break for first time feature writer Lona Williams and first time feature director Michael Patrick Jann… except they couldn’t agree on anything. Difficulties with the film’s biggest star, Kirstie Alley, and a lawsuit from Dairy Queen didn’t help. In this bonus Featurette, Halle Kiefer from the Ruined podcast joins Chris and Lizzie to break down this 1999 box office bomb that somehow became a cult classic. Discover why Lona wasn’t allowed to play the role she’d written for herself, how Kirsten Dunst got cast, and why we have this movie to thank for Amy Adams’ career! Hosted on Acast. See acast.com/privacy https://acast.com/privacy for more information.
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