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Jawbreaker holds up surprisingly well. I say "surprisingly" because most teen movies from the '90s feel very much stuck in the '90s. They might still be funny, but they come stocked with moments of cringeworthy homophobia, or racism, or misogyny that's just part and parcel of dealing with art that's a reflection of its era. But Jawbreaker somehow feels not only like a product of its time, but slightly ahead of it—while also serving as a celebration of the past. And that's probably because a queer person wrote and directed it.

If you took All About Eve, late-'70s John Waters, and Heathers, then threw them into a battle royale–type situation, you'd have Darren Stein's dark comedy about a clique of popular high school girls who accidentally kill one of their own and see the dynamics of their friendships change as a result.

It was the film that gifted unto the world Judy Greer and propelled Rose McGowan to stardom. Released in February 1999, Jawbreaker was the first in a series of movies that year that dealt with the more morbid but still highly stylized side of teenage life: Cruel Intentions, Drop Dead Gorgeous, Election, and But I'm a Cheerleader all hit theaters within months of each other.

Meanwhile, on TV Ryan Murphy was diving into the candy-coated world of the high school dramedy that he would revisit time and time again with Popular, which premiered in September of 1999. With Glee and most recently The Politician, Murphy has continued the tradition of Popular, Jawbreaker, et. al. with teenagers doing and saying very adult things—while often resembling actual grown-ass adults.

These films and shows were exaggerated portraits of high school life—like, how often do slow-motion tandem walks down an empty hallway actually happen? More than that, however, they were a stylized study of popularity from an outsider's perspective. That's where the thematic angst came from—these were stories about outsiders, often told by outsiders, wherein the popular kids were heartless, social-climbing villains with matinee idol looks. And if anything has a timeless resonance, it's how awful high school is.

Leading up to its 20th anniversary Blu-ray release on November 19, NewNowNext chatted with Stein about Jawbreaker's cult status, our mutual love of bad bitches, and that very gay popsicle scene.

What inspired you to write Jawbreaker?

I've always been a huge fan of the horror genre, and I've always loved teen films. I remember these girls growing up in the '80s in the Valley who would kidnap each other on their birthdays as a prank and tie each other to the flagpole in their pajamas. It's similar to a hazing, a sort of humiliation ritual. So I was like, "Well, what if that went wrong? Like what if they accidentally killed her?" That's where the idea came from. It was meant to be a horror movie, and then when I started writing the dialogue, it became a lot snarkier and more about high school politics and belonging, and less about horror.

Darren Stein on the set of Jawbreaker.

What was it like trying to get this film made?

It was really difficult. Every major studio passed on the script because it was so extreme. Finally, a home video division of Sony financed it—not the studio itself. So it was still like an independent film in a way because the budget was 3.5 million, which was much less than the budget for Cruel Intentions or Can't Hardly Wait, which I think was between seven and 15 million. The home video division had only ever acquired movies, and this became the first one they produced. So then after Jawbreaker, the home video division became Sony Screen Gems.

What was the casting process like?

Rose was sort of attached. The home video division of Sony had assured me "A, B, or C actress will make the movie," and Rose was one of those three names. So we had Rose. She was our green light. And then Rebecca [Gayheart] came in and read, and Julie Benz came in and read. And they were both just great. The thing with these characters—they are sort of glamazons. They're larger than life. I remember being a kid and seeing Carrie and Grease, and being like, "Oh, my God, high school's so intimidating. And these people are so old. They look like adults."

Stockard Channing was like a full-fledged 30 when Grease came out.

Totally. I wanted to tap into the terror of that, just make it really obvious. And then Judy was a last-minute discovery.

What a discovery.

We had found someone else for that role, and the girl decided to do a pilot and didn't do the film. And then we were a week away from production and we didn't have Fern/Vylette. And the casting director was like, "This girl just came to L.A. She's from a small town. She just got out of a university for acting school, and she's brilliant." And it was Judy Greer. And she'd only done one indie before Jawbreaker. And she was perfect. She was a literal saving grace, revelation, kind of eureka moment, because it was the hardest part to cast.

Do you have a favorite scene or line from the film?

When Courtney (McGowan) pushes Fern into the mirror. That whole thing is really great because it was all one shot. She and Vylette were just at peak bitch levels. It just felt like something out of All About Eve. I remember I told Judy to blow smoke in Rose's face at one point, and Rose didn't know that was going to happen. So then Rose plucked the cigarette out of Judy's hand and threw it on the ground. That was fun.

Can you speak to the queerness of the film?

Well, obviously Fern's obsession with Liz (Charlotte Ayanna) is definitely queer. It was really never discussed, but I think we all just sort of knew. You have obsessions in high school, and sometimes they're sexual, sometimes they're not. Sometimes they're beyond sexual. They fall into a realm of "other." Either you want to be the person or you're attracted to them, or you're just obsessed in a way that you can't define. And it's not necessarily sexual, but it is queer.

Also, the scene when Rose makes her boyfriend [Ethan Erickson] give head to the Big Stick popsicle—that's completely, overtly queer. I wrote that for myself because that's the scene I wanted to see in a high school movie when I was growing up but never got. Also, Courtney is Satan in heels. I mean, she's a badass, dominant bitch. So it would make sense that she would top the high school quarterback for her own pleasure. It's definitely one of those scenes that I get a lot of feedback on. Like "That's how I knew I was gay!" and "Oh, my God, I wore that scene out on VHS!" Which is great, because that's exactly what it was intended for.

Why do you think Jawbreaker has become a cult classic?

I think people love a bad bitch.

They sure do.

Whether it's Dynasty Mean Girls, Heathers—any kind of archetypal female with unchained, unbound energy, where it's not necessarily about getting permission from men or any kind of masculine intervention. It's this world where women are in control, and I think that's empowering—not just for women, but for anybody. And gay men, of course.

I've always said this about cult films: You can't make a cult film. A cult film needs to become a cult film over time. And that's why it's exciting that Sony is releasing this Blu-ray 20 years later. I think the film is better now than it was when I made it. I think it actually stands up really well. When I first made it, I would watch it like, Oh, I would've done this, this, and this different. I was younger and just a lot closer to it. But I think it has aged well.

Have you ever thought of remaking it or doing a sequel?

Actually, we've had a stage musical in development for about a decade. That's getting closer to happening. And George Northy, who wrote my film G.B.F, and I sold Jawbreaker as an hourlong pilot about two years ago, but it didn't get made. Now I'm thinking about making the stage musical as a musical series. So yeah, there's a lot of talk about remaking Jawbreaker in some capacity. We'll see what happens. I'm not even sure how it's going to land and what exactly is going to happen with it. But there's definitely an appetite for it.