Although Jawbreaker killed the teen dream in 1999, Rebecca Gayheart is returning to her breakout film to school a whole new generation of mean girls.

While on break from rehearsing to play Principal Sherwood in Jawbreaker The Musical, premiering Frida and running through Sept. 20 at Hudson Backstage Theatre, the actress admitted to Deadline that she’s “scared shitless” to make her musical theater debut in the production, but knows the performance will be “so much fun” regardless.

“Well, I’m scared shitless about singing. I’m just going to say that,” she told me at the Hudson Theater Coffee Shop. “I’m not a singer, so I have one solo and I’m really nervous about it. But at the same time, I am going to make it entertaining and fun. And if the singing isn’t amazing, it won’t matter, because the scene will be so much fun.”

Jawbreaker (1999) writer/director Darren Stein, who also penned the book for the musical, expressed how “thrilling” it is to reunite with Gayheart on the stage production, noting her role is actually a combination of two characters from the original.

“It’s so fun to have her playing the Carol Kane role,” said Stein of Principal Sherwood. “Actually, in the musical, the Carol Kane role, Ms. Sherwood, and Pam Grier, the detective, are one role together. So, Rebecca, she’s the principal, but then she becomes empowered to sort of solve the case. So, it’s a really fun arc for that character that wasn’t in the movie.”

In the film, Ms. Sherwood (Kane) was a mousy, well-intentioned school administrator, who ultimately meets the tough and inquisitive Detective Vera Cruz (Grier) when popular student Liz Purr dies.

“So, it’s tricky because they’re polar opposites, as you know. Pam Grier and Carol Kane, it doesn’t get more different,” explained Gayheart of her approach to the role. “So, what I’m trying to do is just really find it for myself, make it my own. I will tell you this Ms. Sherwood goes through a transformation throughout the play. And so, it’s nice. It’s not just Ms. Sherwood, she has her own story and she has her own transformation. Not unlike Fern.”

That onstage evolution includes a solo for Principal Sherwood, complete with some whip-cracking choreo by Jay Jackson (RuPaul’s Drag Race‘s Laganja).

More than a quarter century after playing cool girl with a heart of gold, Julie Freeman, in the movie, Gayheart hopes her former co-stars could take over the role in a potential West End run.

“Well, Darren and I spoke about this. I think that the role of Ms. Sherwood—and in any play, you know, no one does a play for the entirety of the run—so what I think would be great is if Julie Benz, Judy Greer and Rose McGowan all play this role at some point when the musical is happening on the West End in London,” she said. “I think it would be amazing, and I think it would be really fun to see all of us in our different ways of doing it, and exciting for fans of the movie to see all of us come back and return.”

Read on about Rebecca Gayheart’s return to Jawbreaker with her musical theater debut.

DEADLINE: Tell me about the cult legacy of the original Jawbreaker movie and getting to update it for the stage musical.

REBECCA GAYHEART: I mean, it’s pretty incredible that 27 years later, this movie is still relevant, and Darren Stein kept it timeless. I think that’s why every generation keeps finding it, and the message in the movie is really relatable for so many genre, types of people. People ask me all the time, “What is the genre?” And I’m like, “Well, it’s a heartfelt dark comedy.” I don’t know.

DEADLINE: Tell me about playing Principal Sherwood, but as a combination of Ms. Sherwood and Detective Vera Cruz, and also adding your own personal touch to it.

GAYHEART: So, it’s tricky because they’re polar opposites, as you know. Pam Grier and Carol Kane, it doesn’t get more different. So, what I’m trying to do is just really find it for myself, make it my own. I will tell you this Ms. Sherwood goes through a transformation throughout the play. And so, it’s nice. It’s not just Ms. Sherwood, she has her own story and she has her own transformation. Not unlike Vylette.

DEADLINE: I’m excited to see that. And tell me about passing the torch of Julie. Did you give any wisdom to Kristen Seggio in her portrayal?

GAYHEART: No, I think for Kristen, she has a really good handle on it. And I think this is such a different beast, that are all making it their own and they’re doing a wonderful job. So, I’m not offering any tips because I don’t think they’re needed. And if they want, I’m here, of course, but I really don’t think they need it. These kids are so talented.

DEADLINE: What’s been your favorite scene to recreate on stage, or do you have a favorite musical number?

GAYHEART: Well, I’m scared shitless about singing. I’m just going to say that. I’m not a singer, so I have one solo and I’m really nervous about it. But at the same time, I am going to make it entertaining and fun. And if the singing isn’t amazing, it won’t matter, because the scene will be so much fun.

DEADLINE: Well, I’m excited to see it. And I know you’ve done theater before. You were on Broadway, weren’t you?

GAYHEART: Yes, I was in Steel Magnolias, and we did that for just under a year. I played Shelby, which was an iconic role, the Julia Roberts role from the movie. And then I also did Boeing Boeing with Christine Baranski and Mark Rylance and Greg Gorman. And so, that was also really nice. But I’m going to point out that for me, doing a play, even on Broadway, is so different than doing a musical. I don’t even understand some of the language they use. They’re like, “Oh, we’re going to send the plunk track.” And I’m like, “What is that?” They’re like, “Oh, let’s work on the reprisal.” I’m like, “What’s that? Somebody help me.” So, I’m out of my comfort zone. It’s a journey. It’s exciting, but it’s scary and it’s fun.

DEADLINE: Is there anyone else from the original cast that you think should maybe take a swing at one of the stage characters?

GAYHEART: Well, Darren and I spoke about this. I think that the role of Ms. Sherwood—and in any play, you know, no one does a play for the entirety of the run—so what I think would be great is if Julie Benz, Judy Greer and Rose McGowan all play this role at some point when the musical is happening on the West End in London. I think it would be amazing, and I think it would be really fun to see all of us in our different ways of doing it, and exciting for fans of the movie to see all of us come back and return.

DEADLINE: Yeah, absolutely. Also, they announced the Urban Legend reboot, and I’m curious if you have heard anything about what’s going on there or if you would reprise your role?

GAYHEART: So, there’s been a lot of chatter about it. I don’t think anything has come to fruition yet. I would be open to it because I really love Brenda Bates. I think she was ahead of her time. I love that they let a female be a serial killer, and I think she was justified in her actions. So yes, I’m open to it if it’s done right and they stick to the tone of how we originated the movie. I would absolutely love to be a part of it.

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