We rewatched ‘Drop Dead Gorgeous’ to unearth what’s good, what’s bad & what should stay dead forever

Some things deserve to stay in the ’90s. Things like frosted tips. Purple ketchup. And stanning Justin Timberlake.

But what about the film, Drop Dead Gorgeous? Released a quarter of a century ago this week (hehe, feel old yet?), the 1999 mockumentary 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.

Though initially panned by critics upon its release, Drop Dead Gorgeous has since become a cult classic–beloved by queers and outsiders alike.

How about we take this to the next level?

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To celebrate the film’s 25th anniversary, Queerty rewatched Drop Dead Gorgeous–particularly through a 2024 lens–to unbury what held up, what didn’t, and what about the movie should stay dead and never, ever be resurrected… What could possibly go wrong!?!

What had us living (a.k.a. the good)

Drop Dead Gorgeous is so distinctly different from other films of its time, to the point where it’s literally in a beautiful league of its own (see what we did there?). 

Unlike movies such as She’s All That, Never Been Kissed and 10 Things I Hate About You–which basically told the story of boy meets girl, boy falls in love with girl, blah blah blah– Drop Dead Gorgeous told a refreshingly unique story, opting out of romance in favor of satire and unapologetically dark humor. It’s almost like if Saved!, Jawbreaker and Heathers all had a baby, but times a million. Sometimes the humor works, and sometimes it doesn’t (but more on that in a bit).

Not to mention, that cast! It includes Kirsten Dunst (who still deserves an Oscar, damnit!), Ellen Barkin, Allison Janney, Kirstie Alley (before she became problematic), Amy Adams, and a very unexpectedly funny Denise Richards. It’s basically the kind of cast Ryan Murphy would kill for today.

It’s in large part to said cast that makes the film so damn quotable and hilarious too. From hotels next to airports, dances with Jesus, Tilt-a-whirls and “fat ladies in tube tops,” Drop Dead Gorgeous has no shortage of laughs. 

One of my favorite bits is when Kirsten Dunst’s character is talking about a former beauty pageant winner who went on to do great things… including doing commercials for pork products. Oink, oink!:

Another one is when Dunst is describing how people are able to leave her hometown of Mount Rose: “Oh yeah. Guys get out of Mount Rose all the time on hockey scholarships… or prison.” It’s too good!

But alas, there are just too many pithy lines to choose from, so here, you decide on a favorite!

What deserves a nail in the coffin (a.k.a. the bad)

As hilarious as Drop Dead Gorgeous is, there is no denying it is clearly a product of its time. Which is really just a nice way of saying… It is problematic AF! 

It’s something even Lona Williams, the film’s writer, has acknowledged. According to a 2014 piece in Buzzfeed:

Williams’ sense of humor has always skewed dark, which is why Drop Dead Gorgeous is more blistering satire than light humor. (As Matt Malloy put it, “You can say anything around Lona Williams. She’ll go double dark on you.”) In writing the film, Williams didn’t worry about whom she might be offending — she focused on the kind of envelope-pushing that she found funniest.

But the film’s relentless darkness and somewhat bleak message may have been part of what made Drop Dead Gorgeous a tough sell. Even Williams was surprised by her own work when she revisited it recently.

“It was really dark. I kind of forgot,” she said. “That’s what’s funny.” She paused. “It’s not for everyone.” – From “Jesus Loves Winners”: How “Drop Dead Gorgeous” Found Cult Success As A Flop, via Buzzfeed

Here are just a few of the things that don’t hold up today:

In the film, Matt Malloy plays John Dough, one of the beauty pageant judges. There is a running joke throughout the film about how the character has a hankering for ahem, young girls. And while it’s never stated outright, it is very obvious Malloy’s character is a pedo– something that absolutely would not fly today.

There is also the character of Mary Johanson (Alexandra Holden), a former Miss America’s Princess who is now anorexic. In the spirit of the film’s no-holds-barred humor, Mary’s disease is often made the butt of a joke. Holden is no doubt hilarious in this role–as seen by the clip below–but similar to John Dough, there is a no way a character like this would exist in a movie today. 

Additionally, there are several terrible jokes made about race and identity in Drop Dead Gorgeous. For example, one character asks another not to “jew me down” when selling them furniture. During another scene, a character offers to “pay Mexicans in tacos.” There is also a very odd, Rachel Dolezal-esque moment when a white character says they “identify as Asian American,” because they have Asian parents.

Combined, these are all lazy, cheap-shot style jokes that (rightfully) wouldn’t cut it in today’s world.

What deserves to stay six feet under (a.k.a. the absolutely god awful)

Perhaps my biggest grip with Drop Dead Gorgeous is how it portrays people with disabilities. Full disclosure, hi! I am absolutely, 100% disabled so call me biased or extra sensitive or whatever, but it’s a lot. As in, the screenwriter seems to make more digs at disabled people than any other character or community.

Case in point: There is a disabled character in the film who is continuously made fun of in the movie. In fact, over the course of its 98-minute runtime, the R-word is dropped a total of, checks notes, nine times. That’s nearly once every 10 minutes. 

And it’s never used in a “haha, they are using it ironically!” kind of way. No, it is absolutely relentless, demeaning and derogatory–to the point where it made me wonder if the screenwriter had some kind of vendetta against disabled people. It totally took me out of being able to enjoy the movie every time I heard it. Dramatic, I know.

But hey, I get it. Drop Dead Gorgeous is a satire that’s supposed to be making fun of it’s subjects and how people perceive others. Plus, it was made during a time where the R-word was more socially acceptable. But it was still a lot to take as a disabled viewer, especially when watching it through a 2024 lens.

The final verdict

25 years later, Drop Dead Gorgeous has all the makings of a cult classic: a to-die-for cast that bounces off each other like the best trampoline you’ve ever been on, punchy dialogue that makes you laugh until you sob, and just enough outdated humor and nostalgia to make you appreciate “the good ol’ days.”

But like any cult classic, there is plenty of offensive content that makes you appreciate just how much we’ve evolved as a society. It really is quite a beautiful drop dead gorgeous thing!

But what do you think? Do you agree, or are we dead wrong?

Drop Dead Gorgeous is (sadly) not available to stream anywhere online, so you’ll have to buy a physical copy on Amazon

Related

Jesus loves winners: 20 fascinating facts about cult comedy ‘Drop Dead Gorgeous,’ a problematic fave
Celebrating its 25th anniversary this summer, ‘Drop Dead Gorgeous’ was initially a critical and box-office bomb, but has become a cult favorite of the gays.